9,10-dihydro-9,10-ethanoanthracene-12-(2H2-methanol) | 40744-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-dihydro-9,10-ethanoanthracene-12-(2H2-methanol)
• 英文别名: 9,10-ethanoanthracene-11-methanol-13-d2；C,C-dideuterio-(9,10-dihydro-9,10-ethano-anthracen-11-yl)-methanol；C,C-Dideuterio-(9,10-dihydro-9,10-aethano-anthracen-11-yl)-methanol；Dideuterio(15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)methanol
• CAS: 40744-65-8
• 化学式: C₁₇H₁₆O
• 分子量: 238.298
• InChiKey: GKHXDBKHCPINBJ-KBMKNGFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-9,10-ethanoanthracene-12-(2H2-methanol) 以98%的产率得到1,1-二氘代-2-丙烯醇
  参考文献：
  名称：

  Synthesis of δ--α-aminoadipoyl--cysteinyl--allylglycine, and eight deuterated analogues, substrates for the investigation of the mechanism of action of isopenicillin n synthase.

  摘要：

  The synthesis of delta-L-alpha-aminoadipoyl-L-cysteinyl-D-allylglycine (1a) from its component amino acids is described, along with the synthesis of eight analogues (1b-i) specifically deuterated at C-3 and/or C-5 of the allylglycine residue.

  DOI：

  10.1016/s0040-4020(01)91015-4
• 作为产物：
  描述：

  蒽 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 、 硝基苯 为溶剂， 生成 9,10-dihydro-9,10-ethanoanthracene-12-(2H2-methanol)
  参考文献：
  名称：

  Deuterium isotope effects and product studies for the oxidation of N ω -allyl- l -arginine and N ω -allyl- N ω -hydroxy- l -arginine by neuronal nitric oxide synthase

  摘要：

  The nitric oxide synthases (NOS), which require heme, tetrahydrobiopterin, FMN, FAD, and NADPH, catalyze the O-2-dependent conversion of L-arginine to L-citrulline and nitric oxide. N-omega-Allyl-L-arginine, a mechanism-based inactivator of neuronal NOS, also is a substrate, producing L-arginine, acrolein, and H2O (Zhang, H. Q., Dixon, R. P.; Marletta, R I. A.; Nikolic, D.; Van Breemen, R.; Silverman, R. B. J. Am. Chem. SOC. 1997, 119, 10888). Two possible mechanisms for this turnover an proposed, one initiated by allyl C-I-I bond cleavage and the other by guanidino N-H cleavage, and these mechanisms are investigated with the use of N omega-allyl-L-arginine (1), N-omega-[1,1-H-2(2)]allyl-L-arginine (7), N-omega-allyl-L-hydroxy-L-alginine (2) and N-omega-[1,1-H-2(2)]allyl-N-omega-hydroxy-L-arginine (8) as substrates. Significant isotope effects on the two kinetic parameters, k(cat) and k(cat)/k(m) are observed in case of 1 and 7 during turnover, but not with 2 and 8. No kinetic isotope effects are observed for either compound in their role as inactivators. These results support a mechanism involving initial CH bond cleavage of N-omega-allyl-L-arginine followed by hydroxylation and beakdown to products. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(00)00154-1

文献信息

• Iron catalysis of grignard reductions. Mechanism of 1, 3-reductive eliminations from γ-propyl halides
  作者：K.L. Rollick、W.A. Nugent、J.K. Kochi

  DOI：10.1016/s0022-328x(00)86830-8

  日期：1982.2

  3-substituted propyl bromides by Grignard reagents affords propylene and cyclopropane. The reduction to propylene is particularly noteworthy since it formally represents a 1, 2-hydrogen shift. Two key intermediates have been identified in propylene formation, in which 3-methoxypropyl bromide is first catalytically reduced to the magnesium derivative by Grignard reagent. The iron-catalyzed β-elimination

  用格氏试剂对各种3-取代的丙基溴进行铁催化的还原，得到丙烯和环丙烷。还原为丙烯特别值得注意，因为它形式上代表1，2-氢转移。在丙烯的形成中已经发现了两种关键的中间体，其中首先通过格氏试剂将3-甲氧基丙基溴催化还原为镁衍生物。3-甲氧基丙基镁中间体的铁催化的β-消除作用得到烯丙基甲基醚，然后将其还原裂解成丙烯。对反应物中以及两种中间体中氘标记的广泛研究，可以明确地跟踪氢的转移过程。在方案2和3中提出了铁催化的机理，代表了还原为丙烯的第一和第二阶段。
• Mechanistic Aspects of the Reaction of Anionic Iron(0)-Olefin Complexes with Organic Halides. Detection and Characterization of Paramagnetic Organometallic Intermediates
  作者：Dale H. Hill、Masood A. Parvez、Ayusman Sen

  DOI：10.1021/ja00086a022

  日期：1994.4

  The scope and the mechanism of the reactions of [CpFe(COD)][Li(TMEDA) (Cp = C5H5-; COD = 1,5-cyclooctadiene; TMEDA = Me(2)NCH(2)CH(2)NMe(2)), 1, with a number of organic monohalides and geminal dihalides were investigated. With monohalides organic coupling products were observed, and, in:particular, the coupling and cross-coupling of benzyl and allyl halides were studied in detail. The addition of 1 equiv of benzyl halide to 1 in benzene resulted in the initial formation of [CpFe(COD)(CH(2)Ph)], 7. The predominant pathway involved an initial one-electron transfer from [CpFe(COD)](-) to PhCH(2)X to form PhCH(2)X*(-) and [CpFe(COD)]*. PhCH(2)X*(-) quickly disproportionated to form PhCH(2)* and X(-). The benzyl radical then added to [CpFe(COD)]*. Once formed [CpFe(COD)(CH(2)Ph)] reacted with TMEDA in a disproportionation reaction to form 0.5 equiv of the paramagnetic compound, [(TMEDA)Fe(CH(2)Ph)(2)], 3, and 0.5 equiv of FeCp(2). When additional benzyl (or allyl) halide was added, it reacted with [(TMEDA)Fe(CH(2)Ph)(2)] to form the coupled (or cross-coupled) product. This coupling reaction involved the intermediacy of benzyl (and allyl) radicals, and the experimental results were consistent with the product being formed by the coupling of two radicals in solution.
• Ruthenium(II) catalysis in redox fragmentation of allyl ethers
  作者：Robert G. Salomon、James M. Reuter

  DOI：10.1021/ja00455a027

  日期：1977.6
• The Polymerization of Allyl Compounds. VI. The Polymerization of Allyl-1-d₂ Acetate and the Mechanism of its Chain Termination
  作者：Paul D. Bartlett、Fred A. Tate

  DOI：10.1021/ja01097a026

  日期：1953.1
• Synthesis of δ--α-aminoadipoyl--cysteinyl--allylglycine, and eight deuterated analogues, substrates for the investigation of the mechanism of action of isopenicillin n synthase.
  作者：Jack E. Baldwin、Mark Bradley、Nicholas J. Turner、Robert M. Adlington、Andrew R. Pitt、Helen Sheridan

  DOI：10.1016/s0040-4020(01)91015-4

  日期：1991.9

  The synthesis of delta-L-alpha-aminoadipoyl-L-cysteinyl-D-allylglycine (1a) from its component amino acids is described, along with the synthesis of eight analogues (1b-i) specifically deuterated at C-3 and/or C-5 of the allylglycine residue.