(R)-2-(4-chlorophenyl)-4-penteneamide | 494802-87-8

• 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: (R)-2-(4-chlorophenyl)-4-penteneamide
• 英文别名: (R)-2-(4-chlorophenyl)-4-pentenamide；(2R)-2-(4-chlorophenyl)pent-4-enamide
• CAS: 494802-87-8
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: NJWJNUMBVJXNJM-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-(4-chlorophenyl)-4-penteneamide 在 四氧化锇 、 lithium aluminium tetrahydride 、 Jones' agent 作用下， 生成 (R)-(-)-baclofen
  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
• 作为产物：
  描述：

  2-(4-chlorophenyl)-4-pentenenitrile 在 Rhodococcus sp. AJ₂₇₀ 作用下， 以 phosphate buffer 为溶剂， 反应 144.0h， 以44%的产率得到(R)-2-(4-chlorophenyl)-4-penteneamide
  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

文献信息

• [EN] METHOD FOR THE RESOLUTION OF BACLOFEN SALTS<br/>[FR] PROCÉDÉ DE DÉDOUBLEMENT DE SELS DE BACLOFÈNE
  申请人：UNIV ROUEN

  公开号：WO2018015677A1

  公开（公告）日：2018-01-25

  La présente invention concerne le domaine du dédoublement de composés chiraux existant sous la forme de deux antipodes optiques (énantiomères), comme le Baclofène. Plus particulièrement, l'invention concerne la préparation de l'énantiomère pur (R)(-) Baclofène, de nomenclature chimique acide (R)-4-amino-3-(4-chlorophényl)-butanoïque et de son sel d'hydrogénomaléate. Tout spécialement, la présente invention concerne le dédoublement des sels d'hydrogénomaléate du Baclofène racémique par cristallisation préférentielle et notamment par le procédé AS3PC (cristallisation préférentielle polythermique programmée et auto-ensemencée).
• 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
  作者：Mei-Xiang Wang、Sheng-Min Zhao

  DOI：10.1016/s0957-4166(02)00470-6

  日期：2002.8

  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.
• Highly enantioselective biotransformations of 2-aryl-4-pentenenitriles, a novel chemoenzymatic approach to ( R )-(−)-baclofen
  作者：Mei-Xiang Wang、Sheng-Min Zhao

  DOI：10.1016/s0040-4039(02)01449-1

  日期：2002.9

  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.