(2S,3S)-2-Benzyloxymethyl-3-ethyl-2-methyl-oxirane

• 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,3S)-2-Benzyloxymethyl-3-ethyl-2-methyl-oxirane
• 英文别名: (2S,3S)-3-ethyl-2-methyl-2-(phenylmethoxymethyl)oxirane
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: BGKDZPMJQACJHF-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-Benzyloxymethyl-3-ethyl-2-methyl-oxirane 在 zirconyl chloride 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以81%的产率得到
  参考文献：
  名称：

  Regio- and Stereoselective Ring Opening of Epoxides and Aziridines Using Zirconyl Chloride: An Efficient Approach for the Synthesis of β-Chlorohydrins and β-Chloroamines

  摘要：

  在室温下，通过氯锆酸锆催化的环氧化物和氮杂环丙烷的区域选择性和立体选择性开环反应，分别以高产率得到相应的β-氯醇和β-氯胺。

  DOI：

  10.1246/cl.2007.82
• 作为产物：
  描述：

  (2E)-2-methyl-2-penten-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,3S)-2-Benzyloxymethyl-3-ethyl-2-methyl-oxirane
  参考文献：
  名称：

  使用手性环氧醇的对映选择性合成

  摘要：

  环氧醇（1，R CH 2 Ph）在酸催化下通过攻击邻近的碳原子而打开。

  DOI：

  10.1039/c39830000312

文献信息

• Synthesis ofβ-Chlorohydrins in Water
  作者：Biswanath Das、Katta Venkateswarlu、Maddeboina Krishnaiah

  DOI：10.1002/hlca.200790008

  日期：2007.1

  Abstract2,4,6‐Trichloro‐1,3,5‐triazine (TCT, cyanuric chloride) was found to mediate the regio‐ and stereoselective ring opening of epoxides in H2O in the presence of morpholine at room temperature to afford the corresponding β‐chlorohydrins in excellent yields (Table). The transformation is very simple, fast, efficient, and ecologically beneficial.
• Highly regioselective ring opening of epoxides and aziridines using (bromodimethyl)sulfonium bromide
  作者：Biswanath Das、Maddeboina Krishnaiah、Katta Venkateswarlu

  DOI：10.1016/j.tetlet.2006.04.059

  日期：2006.6

  Epoxides and aziridines undergo ring opening efficiently with (bromodimethyl)sulfonium bromide at room temperature to form the corresponding beta-bromohydrins and beta-bromoamines, respectively. The conversions are highly regioselective and afford the products in excellent yields within a short period of time. (c) 2006 Elsevier Ltd. All rights reserved.
• A mild, rapid and highly regioselective ring-opening of epoxides and aziridines with acetic anhydride under solvent-free conditions using ammonium-12-molybdophosphate
  作者：Biswanath Das、V. Saidi Reddy、Fouzia Tehseen

  DOI：10.1016/j.tetlet.2006.07.055

  日期：2006.9

  A highly regioselective ring opening of epoxides and aziridines can be carried out efficiently with acetic anhydride to form the acetates of the corresponding 1,2-diols and 2-amino-alcohols, respectively, using ammonium-12-molybdophosphate (AMP) as a heterogeneous catalyst, at room temperature, in the absence of solvent. (c) 2006 Elsevier Ltd. All rights reserved.
• Regio- and Stereoselective Ring Opening of Epoxides and Aziridines Using Zirconyl Chloride: An Efficient Approach for the Synthesis of β-Chlorohydrins and β-Chloroamines
  作者：Biswanath Das、Maddeboina Krishnaiah、Katta Venkateswarlu

  DOI：10.1246/cl.2007.82

  日期：2007.1

  Zirconyl chloride mediated regio- and stereoselective ring opening of epoxides and aziridines at room temperature affords the corresponding β-chlorohydrins and β-chloroamines, respectively in high yields.

  在室温下，通过氯锆酸锆催化的环氧化物和氮杂环丙烷的区域选择性和立体选择性开环反应，分别以高产率得到相应的β-氯醇和β-氯胺。
• Enantioselective synthesis using chiral epoxy-alcohols
  作者：Ernest W. Colvin、Alan D. Robertson、Shaila Wakharkar

  DOI：10.1039/c39830000312

  日期：——

  The epoxy-alcohol (1, RCH2Ph) opens under acid catalysis by attack at the proximate carbon atom.

  环氧醇（1，R CH 2 Ph）在酸催化下通过攻击邻近的碳原子而打开。