2-(Bromomethyl)-3-pentyloxirane | 192326-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 2-(Bromomethyl)-3-pentyloxirane
• CAS: 192326-35-5
• 化学式: C₈H₁₅BrO
• 分子量: 207.111
• InChiKey: XDRWGNKNJXLWKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-(Bromomethyl)-3-pentyloxirane 在 indium(III) chloride 、 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以77%的产率得到1-辛烯-3-醇
  参考文献：
  名称：

  Selective reductive cleavage of 2,3-epoxybromides by the InCl3–NaBH4 reagent system

  摘要：

  A combination of sodium borohydride and a catalytic amount of indium(Ill) chloride in acetonitrile reduces 2,3-epoxy-bromides to the corresponding allylic alcohols in good yields involving reduction of the bromo moiety followed by selective C-O bond cleavage through a radical process. Several aromatic, cyclic and open-chain bromoepoxides successfully participated in this reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.120
• 作为产物：
  描述：

  2-octenol 在 三溴化磷 、 间氯过氧苯甲酸 作用下， 生成 2-(Bromomethyl)-3-pentyloxirane
  参考文献：
  名称：

  Selective reductive cleavage of 2,3-epoxybromides by the InCl3–NaBH4 reagent system

  摘要：

  A combination of sodium borohydride and a catalytic amount of indium(Ill) chloride in acetonitrile reduces 2,3-epoxy-bromides to the corresponding allylic alcohols in good yields involving reduction of the bromo moiety followed by selective C-O bond cleavage through a radical process. Several aromatic, cyclic and open-chain bromoepoxides successfully participated in this reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.120

文献信息

• US4895942A
  申请人：——

  公开号：US4895942A

  公开（公告）日：1990-01-23
• US4933423A
  申请人：——

  公开号：US4933423A

  公开（公告）日：1990-06-12
• US5001213A
  申请人：——

  公开号：US5001213A

  公开（公告）日：1991-03-19
• Selective reductive cleavage of 2,3-epoxybromides by the InCl3–NaBH4 reagent system
  作者：Brindaban C. Ranu、Subhash Banerjee、Arijit Das

  DOI：10.1016/j.tetlet.2004.09.120

  日期：2004.11

  A combination of sodium borohydride and a catalytic amount of indium(Ill) chloride in acetonitrile reduces 2,3-epoxy-bromides to the corresponding allylic alcohols in good yields involving reduction of the bromo moiety followed by selective C-O bond cleavage through a radical process. Several aromatic, cyclic and open-chain bromoepoxides successfully participated in this reaction. (C) 2004 Elsevier Ltd. All rights reserved.