(S)-2-(4-methylphenyl)-4-pentenoic acid | 494802-95-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-2-(4-methylphenyl)-4-pentenoic acid
• 英文别名: (2S)-2-(4-methylphenyl)pent-4-enoic acid
• CAS: 494802-95-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: HBZHVUXHIIPNEA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-methylphenyl)-4-pentenoic acid 在 碘 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以53%的产率得到(3S,5R)-3-(4-methylphenyl)-5-iodomethyl-γ-butyrolactone
  参考文献：
  名称：

  Synthesis of enantiomerically enriched (S)-(+)-2-aryl-4-pentenoic acids and (R)-(−)-2-aryl-4-pentenamides via microbial hydrolysis of nitriles, a chemoenzymatic approach to stereoisomers of α,γ-disubstituted γ-butyrolactones

  摘要：

  In the presence of the nitrile hydratase amidase-containing Rhodococcus sp. AJ270 whole cell catalyst. 2-aryl-4-pentenenitriles 1 underwent enantioselective hydrolysis under mild conditions to afford (R)-(-)-2-aryl-4-pentenoic acid amides 2 and (S)-(+)-2-aryl-4-pentenoic acids 3 in almost quantitative yield. The amidase involved in the cells shows very high S-enantioselectivity whereas the nitrite hydratase exhibits low to moderate S-enatitioselectivity. The synthesis of stereoisomers of chi,gamma-disubstituted gamma-butyrolactones from iodolactonization of (S)-(+)-2-aryl-4-pentenoic acid was demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00470-6
• 作为产物：
  描述：

  2-(4-methylphenyl)-4-pentenenitrile 在 Rhodococcus sp. AJ₂₇₀ cells 作用下， 以 phosphate buffer 为溶剂， 反应 192.0h， 以26%的产率得到(S)-2-(4-methylphenyl)-4-pentenoic acid
  参考文献：
  名称：

  Highly enantioselective biotransformations of 2-aryl-4-pentenenitriles, a novel chemoenzymatic approach to ( R )-(−)-baclofen

  摘要：

  Catalyzed by Rhodococcus sp. AJ270 microbial cells under mild conditions, a range of racemic 2-aryl-4-pentenenitriles 1 underwent effective hydrolysis to afford excellent yields of enantiomerically pure (R)-(-)-2-aryl-4-pentenamides 2 and (S)-(+)-2-aryl-4-pentenoic acids 3 in most cases. The application of this biotransformation has been shown by a two-step synthesis of (R)-(-)-baclcfen. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01449-1