(2S,3R)-2-Benzyl-3-vinyl-oxirane | 217434-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-2-Benzyl-3-vinyl-oxirane
• 英文别名: (2S,3R)-2-benzyl-3-ethenyloxirane
• CAS: 217434-49-6
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: PMYSHMXXQPPIQD-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-Benzyl-3-vinyl-oxirane 在 sodium perborate 、 bis(cyclohexanyl)borane 作用下， 生成 2-(3-benzyloxiran-2-yl)ethan-1-ol
  参考文献：
  名称：

  An efficient approach to chiral cis-3,4-epoxy alcohols

  摘要：

  A new method for the synthesis of cis-3,4-epoxy alcohols has been developed by employing hydroboration of chiral cis-vinylepoxides or syn-chlorohydrins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01773-0
• 作为产物：
  描述：

  (2S,3S)-3-Chloro-1-phenyl-pent-4-en-2-ol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (2S,3R)-2-Benzyl-3-vinyl-oxirane
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of syn-α-Vinylchlorohydrins and cis-Vinylepoxides

  摘要：

  A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (alpha-haloallyl)lithiums with methoxy-9-BBN or Ipc(2)BOMe followed by treatment with BF3 . OEt(2) leads to (Z)-(gamma-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de greater than or equal to 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-alpha a-halohydrins (de greater than or equal to 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-gamma-chloroallyl]BIpc(2) leads to chiral syn-alpha-chlorohydrins and cis-vinylepoxides in high de (greater than or equal to 90%) and ee(90-99%). Enantioselectivity of reactions of chiral (Z)-(gamma-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other alpha-or gamma-substituted allylboranes. The effects of proportion ofBF(3) . OEt(2) and the relative efficacies of LiNR(2) bases on diastereo- and enantioselectivity of the chloroallylation are reported.

  DOI：

  10.1021/jo960875p

文献信息

• New access to chiral syn-α-Chlorohydrins and cis-vinyloxiranes through chloroallyboration
  作者：Seetharaman Jayaraman、Shaojing Hu、Allan C Oehlschlager

  DOI：10.1016/0040-4039(95)00928-6

  日期：1995.7

  A new method to generate chiral cis-vinyloxiranes from readily available starting materials is reported. (α-Chloroallyl)lithium, generated in situ from LiN(c-Hex)2 and allyl chloride at −95°C, reacts with (−)-β-methoxydiisopinocampheylborane, dIpc2BOMe, to give an ate complex. Treatment of this with BF3·OEt2 leads to the reagent, [(Z)-γ-chloroallyl]BIpc2. Chloroallylboration of aldehydes using the

  报道了一种从容易获得的起始原料中生成手性顺式-乙烯基氧杂环丁烷的新方法。在-95°C下由LiN（c- Hex）2和烯丙基氯原位生成的（α-氯代烯丙基）锂与（-）- β-甲氧基二异opinocampheylborane，d Ipc 2 BOMe反应，得到ate配合物。这种治疗BF 3 ·OET 2个通向试剂，[（Z） - γ -chloroallyl] BIPC 2。使用后者试剂随后消除手性辅助剂的醛类的Chloroallylboration提供顺式- α-氯醇的高de（≥94％）和ee（90–99％）。碱诱导的氯醇环化作用可提供手性顺式-乙烯基环氧乙烷。
• Reaction of 3-chloroallyltrimethylsilane with acid chloride and exploitation of a new regioselective synthesis of αβ-unsaturated epoxide
  作者：Masahito Ochiai、Eiichi Fujita

  DOI：10.1016/s0040-4039(00)77860-9

  日期：1980.1

  reaction of 3-chloroallyltrimethylsilane (1) with acid chloride. The ketone was converted into αβ-unsaturated epoxide (3) regioselectively in good yield via reduction with NaBH4 or LiAlH4 followed by treatment with NaOH. Treatment with methyl lithium instead of reduction gave homologous epoxide (5).

  由3-氯烯丙基三甲基硅烷（1）与酰氯反应合成α-氯-βγ-不饱和酮（2）。通过用NaBH 4或LiAlH 4还原，然后用NaOH处理，将酮以良好的产率选择性地转化为αβ-不饱和环氧化物（3）。用甲基锂而不是还原的处理得到同源的环氧化物（5）。
• Diastereo- and Enantioselective Synthesis of <i>syn</i>-α-Vinylchlorohydrins and <i>cis</i>-Vinylepoxides
  作者：Shaojing Hu、Seetharaman Jayaraman、Allan C. Oehlschlager

  DOI：10.1021/jo960875p

  日期：1996.1.1

  A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (alpha-haloallyl)lithiums with methoxy-9-BBN or Ipc(2)BOMe followed by treatment with BF3 . OEt(2) leads to (Z)-(gamma-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de greater than or equal to 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-alpha a-halohydrins (de greater than or equal to 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-gamma-chloroallyl]BIpc(2) leads to chiral syn-alpha-chlorohydrins and cis-vinylepoxides in high de (greater than or equal to 90%) and ee(90-99%). Enantioselectivity of reactions of chiral (Z)-(gamma-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other alpha-or gamma-substituted allylboranes. The effects of proportion ofBF(3) . OEt(2) and the relative efficacies of LiNR(2) bases on diastereo- and enantioselectivity of the chloroallylation are reported.
• An efficient approach to chiral cis-3,4-epoxy alcohols
  作者：Shaojing Hu、Seetharaman Jayaraman、Allan C. Oehlschlager

  DOI：10.1016/s0040-4039(98)01773-0

  日期：1998.10

  A new method for the synthesis of cis-3,4-epoxy alcohols has been developed by employing hydroboration of chiral cis-vinylepoxides or syn-chlorohydrins. (C) 1998 Elsevier Science Ltd. All rights reserved.