trans-1-hydroxymethyl-2-vinylcyclopentane | 87734-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1-hydroxymethyl-2-vinylcyclopentane
• 英文别名: (2-vinylcyclopentyl)methanol；[(1R,2S)-2-ethenylcyclopentyl]methanol
• CAS: 87734-78-9；90582-64-2；92216-62-1；92216-63-2；119067-64-0
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: LXGVQRGBNSVJCF-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  trans-1-hydroxymethyl-2-vinylcyclopentane 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 trans-2-vinylcyclopentane-1-carboxaldehyde
  参考文献：
  名称：

  Epoxy-silanes in organic synthesis

  摘要：

  DOI：

  10.1016/s0040-4020(01)86648-5
• 作为产物：
  描述：

  4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol 在 吡啶 、 盐酸 、 甲醇 、 重铬酸吡啶 、 Na 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 生成 trans-1-hydroxymethyl-2-vinylcyclopentane
  参考文献：
  名称：

  Cobalt π-cations in carbocyclic ring constructions

  摘要：

  DOI：

  10.1016/s0040-4039(97)82966-8

文献信息

• Organocatalyzed Tsuji–Trost reaction: a new method for the closure of five- and six-membered rings
  作者：Bojan Vulovic、Filip Bihelovic、Radomir Matovic、Radomir N. Saicic

  DOI：10.1016/j.tet.2009.10.006

  日期：2009.12

  A combination of organotransition metal catalysis and organocatalysis allows for Tsuji–Trost 5-exo- and 6-exo-cyclizations of aldehydes. This transformation can also be accomplished as a catalytic asymmetric reaction, which affords vinylcyclopentane derivatives with up to 98%ee.

  有机过渡金属催化和有机催化的结合可实现Tsuji-Trost醛的5 exo-和6 exo-环化反应。该转化也可以作为催化不对称反应来完成，该反应提供了高达98％ee的乙烯基环戊烷衍生物。
• Dual Amine and Palladium Catalysis in Diastereo- and Enantioselective Allene Carbocyclization Reactions
  作者：Meiling Li、Swarup Datta、David M. Barber、Darren J. Dixon

  DOI：10.1021/ol303128s

  日期：2012.12.21

  A pyrrolidine and Pd catalyzed diastereoselective carbocyclization of aldehyde and ketone-linked allenes has been developed. The cooperative organo/metal-catalyzed cyclization reaction, which presumably proceeds via an enamine intermediate, is efficient and broad in scope. Also, it has been extended to a catalytic asymmetric variant using diarylprolinol-based organocatalysts to afford substituted cyclopentane and pyrrolidine reaction products in up to 82% ee.
• Yoshitake, Makoto; Yamamoto, Makoto; Kohmoto, Shigeo, Journal of the Chemical Society. Perkin transactions I, 1991, p. 2161 - 2167
  作者：Yoshitake, Makoto、Yamamoto, Makoto、Kohmoto, Shigeo、Yamada, Kazutoshi

  DOI：——

  日期：——
• Yoshitake, Makoto; Yamamoto, Makoto; Kohmoto, Shigeo, Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1226 - 1228
  作者：Yoshitake, Makoto、Yamamoto, Makoto、Kohmoto, Shigeo、Yamada, Kazutoshi

  DOI：——

  日期：——
• An enantiospecific cobaloxime π-cation initiated carbocyclisation
  作者：Georg Kettschau、Gerald Pattenden

  DOI：10.1016/s0040-4039(98)00163-4

  日期：1998.4

  The cationic carbocyclisation of the allyl silane substituted beta-hydroxycobaloxime (+)-4 was effected by treatment with catalytic amounts of pTSA to form the cyclopentane derivative (+)-5 which was elaborated to the aldehyde (-)-7 via the alcohol (-)-6. Both the optical rotation of (-)-7 and the ee of (-)-6 determined by Mosher esterification revealed that (+)-5 had been formed in an enantiospecific fashion with retention of configuration at the inducing stereogenic centre. (C) 1998 Elsevier Science Ltd. All rights reserved.