methyl (E)-4-hydroperoxy-2-hexenoate | 612845-19-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E)-4-hydroperoxy-2-hexenoate
• 英文别名: methyl (E)-4-hydroperoxyhex-2-enoate
• CAS: 612845-19-9
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: VSYSKRGBBOIIEY-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-hydroperoxy-2-hexenoate 在 2,6-二甲氧基苯酚 、 lipid-HRP 、 三甲氧基磷 作用下， 以 phosphate buffer 、 乙醚 、 甲苯 为溶剂， 反应 26.5h， 生成 (S),(E)-Methyl 4-hydroxy-hex-2-enoate
  参考文献：
  名称：

  Enantioselective reduction of γ-hydroperoxy-α,β-unsaturated carbonyl compounds catalyzed by lipid-coated peroxidase in organic solvents

  摘要：

  The reduction of racemic gamma-hydroperoxy-alpha,beta-unsaturated carbonyl compounds in the presence of lipid-coated horseradish peroxidase as a homogenious catalyst in organic solvents such as toluene, benzene and chlororform containing a small amount of water enantio selectively afforded optical active (R)-alcohols and (S)-hydroperoxides, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00436-1
• 作为产物：
  描述：

  山梨酸甲酯 在 Co(tdcpp) 三乙基硅烷 、 氧气 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 1.0h， 以58%的产率得到methyl (E)-4-hydroperoxy-2-hexenoate
  参考文献：
  名称：

  Enantioselective reduction of γ-hydroperoxy-α,β-unsaturated carbonyl compounds catalyzed by lipid-coated peroxidase in organic solvents

  摘要：

  The reduction of racemic gamma-hydroperoxy-alpha,beta-unsaturated carbonyl compounds in the presence of lipid-coated horseradish peroxidase as a homogenious catalyst in organic solvents such as toluene, benzene and chlororform containing a small amount of water enantio selectively afforded optical active (R)-alcohols and (S)-hydroperoxides, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00436-1

文献信息

• Regioselectivity in the ene reaction of singlet oxygen with alkenes bearing an electron withdrawing group at β- position
  作者：Manolis Stratakis、Michael Orfanopoulos

  DOI：10.1016/s0040-4039(96)02469-0

  日期：1997.2

  Electronic repulsions between a perepoxide intermediate and the allylic functionality in the product forming transition state, direct the regioselectivity in the photooxygenation of trisubstituted alkenes bearing an electron withdrawing group at β- position.

  在形成过渡态的产物中，过氧化物中间体与烯丙基官能团之间的电子排斥作用指导在β-位置带有吸电子基团的三取代烯烃的光氧化中的区域选择性。
• Vasil'ev, A. A.; Cherkaev, G. V., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 5, p. 834 - 840
  作者：Vasil'ev, A. A.、Cherkaev, G. V.

  DOI：——

  日期：——
• Enantioselective reduction of γ-hydroperoxy-α,β-unsaturated carbonyl compounds catalyzed by lipid-coated peroxidase in organic solvents
  作者：Hidetaka Nagatomo、Yoh-ichi Matsushita、Kazuhiro Sugamoto、Takanao Matsui

  DOI：10.1016/s0957-4166(03)00436-1

  日期：2003.8

  The reduction of racemic gamma-hydroperoxy-alpha,beta-unsaturated carbonyl compounds in the presence of lipid-coated horseradish peroxidase as a homogenious catalyst in organic solvents such as toluene, benzene and chlororform containing a small amount of water enantio selectively afforded optical active (R)-alcohols and (S)-hydroperoxides, respectively. (C) 2003 Elsevier Ltd. All rights reserved.