endo,endo-5,6-dideuteriobicyclo<2.2.1>hept-2-ene | 28956-14-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: endo,endo-5,6-dideuteriobicyclo<2.2.1>hept-2-ene
• 英文别名: 3,6-endo-dideuterionorbornene；norbornene-endo,endo-5,6-d2；(1R,4S,5S,6R)-5,6-dideuteriobicyclo[2.2.1]hept-2-ene
• CAS: 28956-14-1
• 化学式: C₇H₁₀
• 分子量: 96.1405
• InChiKey: JFNLZVQOOSMTJK-ZAVZRDCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  endo,endo-5,6-dideuteriobicyclo<2.2.1>hept-2-ene 以75%的产率得到
  参考文献：
  名称：

  EDWARDS, O. E.;DIXON, J.;ELDER, J. W.;KOLT, R. J.;LESAGE, M., CAN. J. CHEM., 1981, 59, N 14, 2096-2115

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-降冰片二烯 在 palladium on activated charcoal 吡啶 、 potassium tert-butylate 、 溴 、 三正丁基氢锡 、 氘 作用下， 以 叔丁醇 为溶剂， 反应 72.0h， 生成 endo,endo-5,6-dideuteriobicyclo<2.2.1>hept-2-ene
  参考文献：
  名称：

  Werstiuk, Nick Henry; Timmins, George; Cappelli, Frank Peter, Canadian Journal of Chemistry, 1980, vol. 58, p. 1738 - 1750

  摘要：

  DOI：

文献信息

• Selective Hydrogenation of Conjugated Dienes Catalyzed by Thiocyanatotris(triphenylphosphine)cobalt(I)
  作者：Taisei Nakayama、Hiroyoshi Kanai

  DOI：10.1246/bcsj.58.16

  日期：1985.1

  bromide, selectively hydrogenated conjugated dienes to the corresponding cis-monomenes. The C2-or/and C3-methyl substituted 1,3-butadienes enhance the reactivity by a factor of 2.3 per one methyl group, while C1- or/and C4-methyl substituted 1,3-butadienes lower the reactivity by a factor of 1/23 per one methyl group. In the hydrogenation of cyclic conjugated dienes α-angle (∠C–C=C) is closely related to

  硫氰酸根合三（三苯基膦）钴（I）由双（硫氰酸根合）双（三苯基膦）钴（II）、三苯基膦、溴化锌、选择性氢化共轭二烯到相应的顺式单烯中原位制备。C2-或/和C3-甲基取代的1,3-丁二烯每一个甲基将反应性提高2.3倍，而C1-或/和C4-甲基取代的1,3-丁二烯则降低反应性每个甲基有 1/23。在环状共轭二烯的加氢中，α角（∠C-C=C）与加氢速率密切相关。环醚的加氢速率大于无环醚的加氢速率，但无环醚的顺式选择性要高得多。氘选择性地添加到 1,3-丁二烯和 2,5-降冰片二烯（双环 [2.2.1] 庚-2,5-二烯）中，得到 3,4-dideuterio-1-butene 和 cis-1，4-dideuterio-2-butene 和endo,endo-5,6-dideuteterionorbornene 和endo,endo-3,5-dideuterionortricyclene。提出了一种机制，该机制源自
• Synthesis and Protonation of [RuH(NBD)(2,6-(Ph₂PCH₂)₂C₆H₃)]
  作者：Sheng Hua Liu、Sze Ming Ng、Ting Bin Wen、Zhong Yuan Zhou、Zhenyang Lin、Chak Po Lau、Guochen Jia

  DOI：10.1021/om020521q

  日期：2002.9.1

  Treatment of [RuCl(PPh3)(PCP)] (PCP = 2,6-(Ph2PCH2)(2)C6H3) With norbornadiene (NBD,) in the presence of CuCl produces [RuCl(NBD)(PCP)]. Reaction of [RuCl(NBD)(PCP)1 with TlOTf gives [Ru(OTf)(NBD)(PCP)], which reacts with NaBH4 to produce [RuH(NBD)(PCP)]. Protonation of [RuH(NBD)(PCP)l with acetic acid in the presence of PPh3 gives norbornene and [Ru(OAc)(PPh3)(PCP)]. Protonation of [RuH(NBD)(PCP)] with HOTf gives norbornene and [Ru(OTf)(NBD)(PCP)]. Protonation of [RuH(NBD)(PCP)l with HOTf in the presence of MeCN gives norbornene, [Ru(MeCN)(NBD)(PCP)]OTf, and [Ru(MeCN)3(PCP)]OTf. In the protonation reactions, the NBD is likely hydrogenated through the dihydrogen intermediate [Ru(H-2)(NBD)(PCP)](+). A computational study shows that hydrogen transfer from the dihydrogen to the NBD ligand of [Ru(H-2)(NBD)(PCP)](+) proceeds through a stepwise mechanism.
• Stereoselectivity in the Rhodium-Catalysed Reductions of Non-Conjugated Dienes
  作者：Bao Nguyen、John M. Brown

  DOI：10.1002/adsc.200900013

  日期：2009.6

  Abstractmagnified imageThe stereochemical course of rhodium‐catalysed addition of hydrogen and catecholborane to bicyclo[2.2.1]heptadiene, and of hydrogen to a range of cyclic dienes has been analysed. For hydroboration, the overall catalytic reaction possesses exo‐selectivity, but the initial step is endo‐selective. For hydrogenation (deuteration), the first step may occur with either exo‐ or endo‐ selectivity, depending on the structure of the diene. This enables a distinction to be made between pathways involving prior dissociation of the diene, and direct addition to the complexed diene without full dissociation. The relative ease of hydrogenation of the first and second double bonds varies markedly with reactant structure, and also depends on the choice of catalyst ligands. For dicyclopentadiene, hydrogenation of the cyclopentene double bond is accompanied by rapid alkene isomerisation, as revealed by deuterium addition. The asymmetric hydrogenation of acyclic skipped meso‐dienes is reported, demonstrating control of relative rates of the two sequential steps, with ees of up to 53% after the first reduction.
• Edwards, Oliver E.; Dixon, John; Elder, John W., Canadian Journal of Chemistry, 1981, vol. 59, p. 2096 - 2115
  作者：Edwards, Oliver E.、Dixon, John、Elder, John W.、Kolt, Ralph J.、Lesage, Maurice

  DOI：——

  日期：——
• Chmielewski, Dietmar; Grevels, Friedrich-Wilhelm; Jacke, Juergen, Angewandte Chemie, 1991, vol. 103, # 10, p. 1361 - 1363
  作者：Chmielewski, Dietmar、Grevels, Friedrich-Wilhelm、Jacke, Juergen、Schaffner, Kurt

  DOI：——

  日期：——