R-1-{2'3'-dihydrobenzo[b]furan-4'-yl}-ethane-1,2-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: R-1-{2'3'-dihydrobenzo[b]furan-4'-yl}-ethane-1,2-diol
• 英文别名: (1R)-1-(2,3-dihydro-1-benzofuran-4-yl)ethane-1,2-diol
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: GISHMZNHTLGCGK-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R,S)-[2',3'-dihydrobenzo[b]furan-4'-yl]-1,2-oxirane 在 phosphate buffer 、 Rhodotorula glutinis SC 16293 作用下， 以 various solvent(s) 为溶剂， 反应 5.5h， 生成 (S)-4-(oxiran-2-yl)-2,3-dihydrobenzofuran 、 (S)-1-{2',3'-dihydrobenzo[b]furan-4'-yl}-ethane-1,2-diol 、 R-1-{2'3'-dihydrobenzo[b]furan-4'-yl}-ethane-1,2-diol
  参考文献：
  名称：

  Stereospecific enzymatic hydrolysis of racemic epoxide: a process for making chiral epoxide

  摘要：

  Among various microbial cultures evaluated, Rhodotorula glutinis SC 16293 and Aspergillus niger SC 16311 catalyzed the stereospecific hydrolysis of the racemic epoxide, RS-1-{2',3'-dihydrobenzo[b]furan-4'-yl}-1,2-oxirane, 1 to the corresponding R-diol, R-1-{2',3'-dihydrobenzo[b]furan-4'-yl}-ethane-1,2-diol, 3. The S-epoxide, S-1-{2',3'-dihydrobenzo[b]furan-4'-yl}-1,2 remained unreacted in the reaction mixture. A reaction yield of 45-50% (theoretical maximum yield is 50%) and an enantiomeric excess (ee) of >95% were obtained for unreacted S-epoxide 2 using each culture. Addition of 10% methyl tert-butyl ether to an aqueous reaction mixture during hydrolysis by R. glutinis improved the ee of the unreacted S-epoxide 2 to >99% (yield 48%) and that of the R-diol 3 to 79%. Unlike R. glutinis, hydrolysis of racemic epoxide 1 in the presence of 10% methyl tert-butyl ether by A. niger showed an adverse effect and gave S-epoxide 2 in 54% yield and 49% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00326-2

文献信息

• Stereospecific enzymatic hydrolysis of racemic epoxide: a process for making chiral epoxide
  作者：Animesh Goswami、Michael J. Totleben、Ambarish K. Singh、Ramesh N. Patel

  DOI：10.1016/s0957-4166(99)00326-2

  日期：1999.8

  Among various microbial cultures evaluated, Rhodotorula glutinis SC 16293 and Aspergillus niger SC 16311 catalyzed the stereospecific hydrolysis of the racemic epoxide, RS-1-2',3'-dihydrobenzo[b]furan-4'-yl}-1,2-oxirane, 1 to the corresponding R-diol, R-1-2',3'-dihydrobenzo[b]furan-4'-yl}-ethane-1,2-diol, 3. The S-epoxide, S-1-2',3'-dihydrobenzo[b]furan-4'-yl}-1,2 remained unreacted in the reaction mixture. A reaction yield of 45-50% (theoretical maximum yield is 50%) and an enantiomeric excess (ee) of >95% were obtained for unreacted S-epoxide 2 using each culture. Addition of 10% methyl tert-butyl ether to an aqueous reaction mixture during hydrolysis by R. glutinis improved the ee of the unreacted S-epoxide 2 to >99% (yield 48%) and that of the R-diol 3 to 79%. Unlike R. glutinis, hydrolysis of racemic epoxide 1 in the presence of 10% methyl tert-butyl ether by A. niger showed an adverse effect and gave S-epoxide 2 in 54% yield and 49% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.