1-(5-(2-chlorophenyl)furan-2-yl)ethane-1,2-diyl diacetate | 1312997-59-3

• 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: 1-(5-(2-chlorophenyl)furan-2-yl)ethane-1,2-diyl diacetate
• CAS: 1312997-59-3
• 化学式: C₁₆H₁₅ClO₅
• 分子量: 322.745
• InChiKey: JSEZHTCUHTZSFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.74
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(5-(2-chlorophenyl)furan-2-yl)ethane-1,2-diyl diacetate 在 Burkholderia cepacia lipase 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 1-(5-(2-chlorophenyl)furan-2-yl)-2-hydroxyethyl acetate
  参考文献：
  名称：

  Sequential use of regio- and stereoselective lipases for the efficient kinetic resolution of racemic 1-(5-phenylfuran-2-yl)ethane-1,2-diols

  摘要：

  Possible routes for the enzymatic transformation of various substituted 1-(5-phenylfuran-2-yl)ethane-1,2-diols and their mono- and diacetylated counterparts were studied. Combining the regioselectivity of LPS mediated acylation of the starting racemic diols, the stereoselectivity of LAK shown in the enantiomer selective transformation of the previously formed racemic primary acetates and the LPS mediated mild hydrolysis-alcoholysis of the resolution products, an efficient preparative scale procedure for the synthesis of various highly enantiomerically enriched (R)- and (S)-phenylfuran-2-yl-ethane-1,2-diols has been developed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.006
• 作为产物：
  描述：

  1-[5-(2-氯苯基)-2-呋喃基]乙酮 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 pyridinium hydrobromide perbromide 、 18-冠醚-6 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.5h， 生成 1-(5-(2-chlorophenyl)furan-2-yl)ethane-1,2-diyl diacetate
  参考文献：
  名称：

  Sequential use of regio- and stereoselective lipases for the efficient kinetic resolution of racemic 1-(5-phenylfuran-2-yl)ethane-1,2-diols

  摘要：

  Possible routes for the enzymatic transformation of various substituted 1-(5-phenylfuran-2-yl)ethane-1,2-diols and their mono- and diacetylated counterparts were studied. Combining the regioselectivity of LPS mediated acylation of the starting racemic diols, the stereoselectivity of LAK shown in the enantiomer selective transformation of the previously formed racemic primary acetates and the LPS mediated mild hydrolysis-alcoholysis of the resolution products, an efficient preparative scale procedure for the synthesis of various highly enantiomerically enriched (R)- and (S)-phenylfuran-2-yl-ethane-1,2-diols has been developed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.006