PMID-sentid	Pub_year	Sent_text	compound_name	comp_offset	prot_official_name	organism	prot_offset
34611680-3	2021	Similarly, from SbCl3, a cationic formal SbI compound and from RhCl3, (RhI(HMB)(COD))+ and (RhI(COD)2)+ (HMB = C6Me6, COD = 1,5-cyclooctadiene) are formed as (Al(ORF)4)- salts when reacted with Ga+.	1,5-cyclooctadiene	124-142	cortactin binding protein 2	Homo sapiens	158-167
32959513-1	2021	The earth-metal olefin complex [Ga I (COD) 2 ] + [Al(OR F ) 4 ] - (COD = 1,5-cyclooctadiene; R F = C(CF 3 ) 3 ) constitutes the first homoleptic olefin complex of any main-group metal accessible as a bulk compound.	1,5-cyclooctadiene	73-91	cortactin binding protein 2	Homo sapiens	50-61
34339213-6	2021	The 1,5-cyclooctadiene (COD) ligand contained in the precatalyst CODPd(CH2TMS)2 (Pd1) was shown to be a beneficial additive.	1,5-cyclooctadiene	4-22	spermatogenesis associated 2	Homo sapiens	81-84
34339213-6	2021	The 1,5-cyclooctadiene (COD) ligand contained in the precatalyst CODPd(CH2TMS)2 (Pd1) was shown to be a beneficial additive.	1,5-cyclooctadiene	24-27	spermatogenesis associated 2	Homo sapiens	81-84
34180473-2	2021	In the case of Ni(COD)2 (COD = 1,5-cyclooctadiene), a dianionic sandwich-like cluster (Ni{Ge9(Hyp)3}2)2- (1) was obtained, in line with a simple ligand substitution reaction of COD by (Ge9(Hyp)3)-.	1,5-cyclooctadiene	31-49	COD2	Homo sapiens	15-23
34467299-1	2021	The complexes (RhX(COD))2 (X = Cl, Br; COD = 1,5-cyclooctadiene) form cocrystals with sigma-hole iodine donors.	1,5-cyclooctadiene	45-63	chromosome 12 open reading frame 73	Homo sapiens	35-37
30521318-1	2018	In the presence of a catalytic amount of Ni(cod)2 (cod = 1,5-cyclooctadiene) and PCy3 (Cy = cyclohexyl), the cross-tetramerization of tetrafluoroethylene (TFE), ethylene, alkynes, and aldehydes leads to a variety of fluorine-containing enone derivatives.	1,5-cyclooctadiene	57-75	COD2	Homo sapiens	41-49
32065839-1	2020	We report that Ni(COD)(DQ) (COD = 1,5-cyclooctadiene, DQ = duroquinone), an air-stable 18-electron complex originally described by Schrauzer in 1962, is a competent precatalyst for a variety of nickel-catalyzed synthetic methods from the literature.	1,5-cyclooctadiene	36-52	retinitis pigmentosa GTPase regulator	Homo sapiens	28-35
30500210-6	2019	When 3 was allowed to react with Ni(cod)2 (cod = 1,5-cyclooctadiene), the unique {[SiII(Xant)SiII]GeI}2NiII complex with a three-membered ring Ge2Ni-metallacycle was obtained via reductive coupling of two Ge0 atoms on the Ni center.	1,5-cyclooctadiene	49-67	COD2	Homo sapiens	33-41
32412179-2	2020	Bis(alpha-hydroxycyclopentyl)phosphine oxide reacts with [PdCl2 (COD)] (COD=1,5-cyclooctadiene) to give a new palladium complex trans-[PdCl2 {P(OH)(cyclo-C5 H8 -1-OH)2 }2 ] (3 a, isolated yield 11 %) bearing phosphinous acid as a ligand formed via tautomerization of the phosphine oxide.	1,5-cyclooctadiene	76-94	phosducin like 2	Homo sapiens	58-63
31576866-1	2019	The reaction of the phosphine functionalized chlorogermylene 1 with Ni(COD)2 (COD = 1,5-cyclooctadiene) afforded the bis-chlorogermylene ligated nickel(0) complex 2 in high yield.	1,5-cyclooctadiene	86-102	COD2	Homo sapiens	71-76
31576866-1	2019	The reaction of the phosphine functionalized chlorogermylene 1 with Ni(COD)2 (COD = 1,5-cyclooctadiene) afforded the bis-chlorogermylene ligated nickel(0) complex 2 in high yield.	1,5-cyclooctadiene	86-102	retinitis pigmentosa GTPase regulator	Homo sapiens	78-85
30816389-3	2019	When reduction is performed in the presence of 1,5-cyclooctadiene (COD), [Ni(COD)2] is obtained.	1,5-cyclooctadiene	47-65	COD2	Homo sapiens	77-82
29149562-1	2017	In the presence of a catalytic amount of Ni(cod)2 (cod = 1,5-cyclooctadiene) and PCy3 (Cy = cyclohexyl), the cross-tetramerization of tetrafluoroethylene (TFE), alkynes, and ethylene occurred in a highly selective manner to afford a variety of 1,3-dienes with a 3,3,4,4-tetrafluorobutyl chain.	1,5-cyclooctadiene	57-75	COD2	Homo sapiens	41-49
29441396-2	2018	Reaction of (PPh2)2BMes with Ni(COD)2 or Pt(COD)Me2 (COD = 1,5-cyclooctadiene) results in gradual COD displacement to give [eta3-P,B,P-(PPh2)2BMes]Ni(COD) (3) or [eta3-P,B,P-(PPh2)2BMes]Pt(CH3)2 (6).	1,5-cyclooctadiene	59-77	COD2	Homo sapiens	32-37
29323365-3	2018	In contrast, reaction of 1a with [Ir2Cl2(COD)2] (COD = 1,5-cyclo-octadiene) affords the complex [IrCl(COD){kappa2-P,P"-H2C(NCH2PPh2)2C10H6}], thermolysis of which affords cyclo-octene and the pincer-NHC complex [IrCl{kappa3-C,P,P"-C(NCH2PPh2)2C10H6}].	1,5-cyclooctadiene	55-74	COD2	Homo sapiens	41-46
29155467-1	2018	The recently published purely metallo-organic NiI salt [Ni(cod)2 ][Al(ORF )4 ] (1, cod=1,5-cyclooctadiene, RF =C(CF3 )3 ) provides a starting point for a new synthesis strategy leading to NiI phosphine complexes, replacing cod ligands by phosphines.	1,5-cyclooctadiene	87-105	cortactin binding protein 2	Homo sapiens	70-76
29116776-3	2017	We report detailed mechanistic analysis of the hydrogenolysis of diaryl ethers catalyzed by the combination of Ni(COD)2 (COD = 1,5-cyclooctadiene) and an N-heterocyclic carbene (NHC).	1,5-cyclooctadiene	127-145	COD2	Homo sapiens	111-119
26952589-2	2016	Treatment of the homoleptic, 8-coordinate M(NP)4 monometallic precursors with Ni(COD)2 (COD = 1,5-cyclooctadiene) yielded the heterobimetallic complexes (kappa(2)-NP)M(mu2-NP)3Ni (M = Ti, Zr, Hf).	1,5-cyclooctadiene	94-112	COD2	Homo sapiens	81-86
27629250-1	2016	Various aryl-, alkenyl-, and/or alkyllithium species reacted smoothly with aryl and/or benzyl ethers with cleavage of the inert C-O bond to afford cross-coupled products, catalyzed by commercially available [Ni(cod)2 ] (cod=1,5-cyclooctadiene) catalysts with N-heterocyclic carbene (NHC) ligands.	1,5-cyclooctadiene	224-242	COD2	Homo sapiens	211-216
26426089-2	2015	The reaction of [LSi:]2 (1, L = PhC(NtBu)2) with [Ir(cod)Cl]2 (cod = 1,5-cyclooctadiene) in toluene at ambient temperature afforded the base-stabilized silicon(I) dimer-iridium complex [LSi{Ir(cod)-mu-Cl-Ir(cod)}SiL][(cod)IrCl2] (2).	1,5-cyclooctadiene	69-87	STIL centriolar assembly protein	Homo sapiens	212-215
27059164-1	2016	N-heterocyclic carbene (NHC) ligands with naphthyl side chains were employed for the synthesis of unsaturated, yet isolable [(NHC)Ir(cod)](+) (cod=1,5-cyclooctadiene) complexes.	1,5-cyclooctadiene	147-165	high mobility group nucleosomal binding domain 4	Homo sapiens	0-22
27059164-1	2016	N-heterocyclic carbene (NHC) ligands with naphthyl side chains were employed for the synthesis of unsaturated, yet isolable [(NHC)Ir(cod)](+) (cod=1,5-cyclooctadiene) complexes.	1,5-cyclooctadiene	147-165	high mobility group nucleosomal binding domain 4	Homo sapiens	24-27
21956660-3	2011	In contrast to the analogous complexes that contain cis,cis-1,5-cyclooctadiene (cod), this complex shows well-resolved NMR spectroscopic signals.	1,5-cyclooctadiene	80-83	suppressor of cytokine signaling 1	Homo sapiens	56-61
23780721-2	2013	This transformation gives direct access to [(123)I]- and [(125)I]-imaging agents for single photon emission computed tomography (SPECT), such as 5-[(123)I]-A85380 (see scheme, Boc = tert-butyloxycarbonyl, cod = 1,5-cyclooctadiene, TFA = trifluoroacetic acid).	1,5-cyclooctadiene	211-229	BOC cell adhesion associated, oncogene regulated	Homo sapiens	176-179
23712914-2	2013	High levels of enantioselectivity and high yields were achieved with this operationally easy and robust protocol, the use of which was demonstrated in the synthesis of GPR40 receptor agonist AMG 837. cod = 1,5-cyclooctadiene.	1,5-cyclooctadiene	206-224	free fatty acid receptor 1	Homo sapiens	168-173
26226412-5	2015	These complexes were synthesized in higher yields from the reaction of with Ni(COD)2, where COD = 1,5-cyclooctadiene.	1,5-cyclooctadiene	98-116	COD2	Homo sapiens	79-84
25693968-2	2015	Reported herein is that 1,4-dilithio-1,3-butadienes reacted with [Ni(cod)2] (cod = 1,5-cyclooctadiene) to deliver dilithionickeloles.	1,5-cyclooctadiene	83-101	COD2	Homo sapiens	69-74
25283156-3	2014	The use of our highly active [Ir(cod)(IMes)(PPh3 )][PF6 ] (cod=1,5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective beta-activation and labelling of a range of alpha,beta-unsaturated compounds with differing steric and electronic properties.	1,5-cyclooctadiene	63-81	caveolin 1	Homo sapiens	44-48
25283156-3	2014	The use of our highly active [Ir(cod)(IMes)(PPh3 )][PF6 ] (cod=1,5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective beta-activation and labelling of a range of alpha,beta-unsaturated compounds with differing steric and electronic properties.	1,5-cyclooctadiene	63-81	sperm associated antigen 17	Homo sapiens	52-55
24526274-4	2014	In these media, spontaneous decomposition of Ni(COD)2 (COD = 1,5-cyclooctadiene) in the absence of H2 occurred giving small NPs (<=4 nm) with narrow size distributions.	1,5-cyclooctadiene	61-79	COD2	Homo sapiens	45-53
23659205-5	2013	The calculations reproduced and rationalized the experimentally observed selectivities and provided an explanation for the remarkable alteration in the product distribution when the catalyst precursor is changed from [RhCl(nbd)]2 (nbd = norbornadiene) to complexes containing noncoordinating counterions ([Rh(cod)2X]; X = OTf, BF4, PF6; cod = 1,5-cyclooctadiene).	1,5-cyclooctadiene	343-361	sperm associated antigen 17	Homo sapiens	332-335
17330965-7	2007	Cycloocta-1,5-diene elimination from, and single methyl protonation of, Pt(CH3)2(cod) with 1 equiv of 2.HH in toluene at ambient temperature affords the neutral complex Pt(CH3)(2.H-), 5a, in which 2.H- functions effectively in a kappa3-PNN" coordination mode.	1,5-cyclooctadiene	0-19	pinin, desmosome associated protein	Homo sapiens	236-239
29711974-1	2001	The precatalyst [Cp*RuCl(cod)] promotes the head-to-head cyclodimerization of propargylic alcohols and the formation of novel alkylidene cyclobutenes (see scheme; Cp*=C5 Me5 , cod=1,5-cyclooctadiene) by addition of carboxylic acid to the Ru(eta4 -cyclobutadiene) intermediate and dehydration.	1,5-cyclooctadiene	180-198	FAT atypical cadherin 1	Homo sapiens	170-173
21588809-2	2010	The rhodium(I) coordination sphere is completed by the Cl atom and the COD [= 1,5-cyclo-octa-diene] ligand inter-acting through the pi-electrons of the double bonds.	1,5-cyclooctadiene	78-98	small nuclear ribonucleoprotein polypeptides B and B1	Homo sapiens	71-74
17441112-1	2006	In the 1,4-addition of phenylboronic acid to alpha,beta-unsaturated ketones, [Rh(OH)(cod)]2 has a much higher catalytic activity than [Rh(OH)(binap)]2 (cod = 1,5-cyclooctadiene, binap = 2,2"-bis(diphenylphosphanyl)-1,1"-binaphthyl).	1,5-cyclooctadiene	158-176	COD2	Homo sapiens	85-91