(2S)-2-ethenyl-2-(phenylmethoxymethyl)oxirane | 1253120-60-3

• 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)-2-ethenyl-2-(phenylmethoxymethyl)oxirane
• CAS: 1253120-60-3
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: HDYSHBUNVJYIGX-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (+/-)-2-benzyloxymethyl-2-vinyloxirane 在 Bacillus subtilis Tamy 2 strain 作用下， 以 水 、 甘油 为溶剂， 反应 96.0h， 生成 (2S)-2-ethenyl-2-(phenylmethoxymethyl)oxirane 、 (2R)-2-ethenyl-2-(phenylmethoxymethyl)oxirane 、 (R)-2-((benzyloxy)methyl)but-3-ene-1,2-diol
  参考文献：
  名称：

  The scope and limitation of the regio- and enantioselective hydrolysis of aliphatic epoxides using Bacillus subtilis epoxide hydrolase, and exploration toward chirally differentiated tris(hydroxymethyl)methanol

  摘要：

  The substrate specificity of an engineered Bacillus subtilis epoxide hydrolase, which so far had shown high activity and enantioselectivity with 1-benzyloxymethyl-1 -methyloxirane, has been studied by altering the methyl substituent into hydrogen, oxygen-containing functionalities, and unsaturated homologs. High enantioselectivity (E = 44) was observed with 1-benzyloxymethyl-1-vinyloxirane with a proper catalytic activity. The elaboration of the reaction conditions and work-up procedures enabled a preparative-scale kinetic resolution, to give (R)-2-benzyloxymethyl-3-butene-1,2-diol and its antipodal (R)-epoxide in high ees. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.014

文献信息

• The scope and limitation of the regio- and enantioselective hydrolysis of aliphatic epoxides using Bacillus subtilis epoxide hydrolase, and exploration toward chirally differentiated tris(hydroxymethyl)methanol
  作者：Ken-ichi Shimizu、Maki Sakamoto、Manabu Hamada、Toshinori Higashi、Takeshi Sugai、Mitsuru Shoji

  DOI：10.1016/j.tetasy.2010.07.014

  日期：2010.8

  The substrate specificity of an engineered Bacillus subtilis epoxide hydrolase, which so far had shown high activity and enantioselectivity with 1-benzyloxymethyl-1 -methyloxirane, has been studied by altering the methyl substituent into hydrogen, oxygen-containing functionalities, and unsaturated homologs. High enantioselectivity (E = 44) was observed with 1-benzyloxymethyl-1-vinyloxirane with a proper catalytic activity. The elaboration of the reaction conditions and work-up procedures enabled a preparative-scale kinetic resolution, to give (R)-2-benzyloxymethyl-3-butene-1,2-diol and its antipodal (R)-epoxide in high ees. (C) 2010 Elsevier Ltd. All rights reserved.