2-[(2S)-oxiran-2-yl]ethyl acetate | 1092554-94-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(2S)-oxiran-2-yl]ethyl acetate
• CAS: 1092554-94-3
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: CYJBIBDHIZXACV-LURJTMIESA-N

物化性质

• 沸点：
  158.3±13.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2S)-oxiran-2-yl]ethyl acetate 在 lipase from Rhizomucor miehei, expressed in Aspergillus oryzae 作用下， 反应 14.0h， 以92%的产率得到(S)-(2-hydroxyethyl)oxirane
  参考文献：
  名称：

  Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology

  摘要：

  Novel epoxide hydrolases in Yarrowia lipolytica have been shown to hydrolyse a variety of functionalised epoxides with good to excellent stereoselectivity and at high volumetric productivities. Individual biotransformation products have been converted into optically active (R)-(tetrahydrofun-2-yl)methanol (6), (S)-N-benzyl-3-hydroxypyrrolidine (7), (S)-3-hydroxytetrahydrothiophene (8), (S)-N-benzyl-3-acetoxypiperidine (10), (S)-3-hydroxytetrahydrofuran (16) and (R)-[(S)-N-benzylpyrrolidin-2-yl](phenyl)-methanol (20). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.097
• 作为产物：
  描述：

  2-(oxiran-2-yl)ethyl acetate 在 Yarrowia lipolytica epoxide hydrolase (Oxy-3) 、 水 作用下， 以20%的产率得到2-[(2S)-oxiran-2-yl]ethyl acetate
  参考文献：
  名称：

  Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology

  摘要：

  Novel epoxide hydrolases in Yarrowia lipolytica have been shown to hydrolyse a variety of functionalised epoxides with good to excellent stereoselectivity and at high volumetric productivities. Individual biotransformation products have been converted into optically active (R)-(tetrahydrofun-2-yl)methanol (6), (S)-N-benzyl-3-hydroxypyrrolidine (7), (S)-3-hydroxytetrahydrothiophene (8), (S)-N-benzyl-3-acetoxypiperidine (10), (S)-3-hydroxytetrahydrofuran (16) and (R)-[(S)-N-benzylpyrrolidin-2-yl](phenyl)-methanol (20). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.097

文献信息

• Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology
  作者：Daniel P. Pienaar、Robin K. Mitra、Thomas I. van Deventer、Adriana L. Botes

  DOI：10.1016/j.tetlet.2008.08.097

  日期：2008.11

  Novel epoxide hydrolases in Yarrowia lipolytica have been shown to hydrolyse a variety of functionalised epoxides with good to excellent stereoselectivity and at high volumetric productivities. Individual biotransformation products have been converted into optically active (R)-(tetrahydrofun-2-yl)methanol (6), (S)-N-benzyl-3-hydroxypyrrolidine (7), (S)-3-hydroxytetrahydrothiophene (8), (S)-N-benzyl-3-acetoxypiperidine (10), (S)-3-hydroxytetrahydrofuran (16) and (R)-[(S)-N-benzylpyrrolidin-2-yl](phenyl)-methanol (20). (C) 2008 Elsevier Ltd. All rights reserved.