(S)-(3-溴丙基)环氧乙烷 | 1092554-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: (S)-(3-溴丙基)环氧乙烷
• 英文名称: 5-bromopentene oxide
• 英文别名: (S)-(3-bromopropyl)oxirane；(2S)-2-(3-Bromopropyl)oxirane；(2S)-2-(3-bromopropyl)oxirane
• CAS: 1092554-93-2
• 化学式: C₅H₉BrO
• 分子量: 165.03
• InChiKey: ZRRZAIJKJYIGIV-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  7
• 可旋转键数：
  3
• 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：

  (S)-(3-溴丙基)环氧乙烷 在 溶剂黄146 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(2S)-1,5-dibromopentan-2-ol
  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：

  5-溴-1-戊烯 在 titanium(IV) isopropylate 、 四丁基高氯酸铵 、 C₃₂H₂₁F₁₀N₃O₄ 、 双氧水 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 以92 %的产率得到(S)-(3-溴丙基)环氧乙烷
  参考文献：
  名称：

  钛 Salalen 催化对映选择性苯甲基羟基化

  摘要：

  顺式-1,2-二氨基环己烷（顺式-DACH）Ti salalen络合物（R=NO 2）被证明可以有效催化以H 2 O 2作为氧化剂的对映选择性苄基羟基化。四氢化萘和茚满衍生物转化为 ee 高达 98% 的苯甲醇。酮的过度氧化可以忽略不计。环氧化反应同样有效，在 0.1 mol% 催化剂负载量下，1-癸烯转化为其环氧化物，产率达 90%，ee 达 94%。

  DOI：

  10.1002/anie.202306584

文献信息

• Predictable Stereoselective and Chemoselective Hydroxylations and Epoxidations with P450 3A4
  作者：Aaron T. Larsen、Erin M. May、Karine Auclair

  DOI：10.1021/ja200551y

  日期：2011.5.25

  Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.
• 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.