(+/-)-isopropyl 3-hydroxycyclopent-1-ene-1-carboxylate | 472963-10-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (+/-)-isopropyl 3-hydroxycyclopent-1-ene-1-carboxylate
• 英文别名: Propan-2-yl 3-hydroxycyclopentene-1-carboxylate
• CAS: 472963-10-3
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: WTGRIRCWCJAEPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-isopropyl 3-hydroxycyclopent-1-ene-1-carboxylate 在 Geotrichum candidum 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以151 mg的产率得到(+)-(R)-isopropyl 3-hydroxycyclopent-1-ene-1-carboxylate
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure isopropyl (3R)- and (3S)-3-hydroxycyclohex-1-ene-1-carboxylates and their reduction to isomers of isopropyl 3-hydroxy-cyclohexane-1-carboxylate

  摘要：

  Reduction of an alpha,beta-unsaturated cyclic ketone with Geotrichum candidum affords the corresponding (S)-allylic alcohol, while enantiospecific oxidation of the corresponding racemic alcohols leases the (R)-enantiomer unchanged, giving access to both enantiomeric forms. Subsequent chemical reduction of the double bond of these homochiral allylic alcohol allows all isomers of the corresponding cyclohexanols to be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00152-0
• 作为产物：
  描述：

  isopropyl 3-oxocyclopent-1-ene-1-carboxylate 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以71%的产率得到(+/-)-isopropyl 3-hydroxycyclopent-1-ene-1-carboxylate
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure isopropyl (3R)- and (3S)-3-hydroxycyclohex-1-ene-1-carboxylates and their reduction to isomers of isopropyl 3-hydroxy-cyclohexane-1-carboxylate

  摘要：

  Reduction of an alpha,beta-unsaturated cyclic ketone with Geotrichum candidum affords the corresponding (S)-allylic alcohol, while enantiospecific oxidation of the corresponding racemic alcohols leases the (R)-enantiomer unchanged, giving access to both enantiomeric forms. Subsequent chemical reduction of the double bond of these homochiral allylic alcohol allows all isomers of the corresponding cyclohexanols to be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00152-0