methyl 4-anilino-4-(4-chlorophenyl)-2-nitrobutanoate | 1036637-42-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 4-anilino-4-(4-chlorophenyl)-2-nitrobutanoate
• 英文别名: methyl 4-(4-chlorophenyl)-2-nitro-4-(phenylamino)butanoate；Methyl 4-anilino-4-(4-chlorophenyl)-2-nitrobutanoate
• CAS: 1036637-42-9
• 化学式: C₁₇H₁₇ClN₂O₄
• 分子量: 348.786
• InChiKey: HIKQVXQSKCVMKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl (1S,2R)-1-nitro-2-(4-chlorophenyl)-cyclopropanecarboxylate 、 苯胺 在 nickel(II) perchlorate hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以74%的产率得到methyl 4-anilino-4-(4-chlorophenyl)-2-nitrobutanoate
  参考文献：
  名称：

  A Mild Procedure for the Lewis Acid-Catalyzed Ring-Opening of Activated Cyclopropanes with Amine Nucleophiles

  摘要：

  The Lewis acid-catalyzed ring-opening of methyl 1-nitrocyclopropanecarboxylates with amine nucleophiles is described. The reaction proceeds at room temperature and with complete preservation of the enantiomeric purity from the electrophilic center of the cyclopropane to the acyclic product. The methodology was applied in an enantioselective synthesis of the dual serotonin/norepinephrine reuptake inhibitor (3R)-3-(1H-indol-1-yl)-N-methyl-3-phenylpropan-1-amine.

  DOI：

  10.1021/ol8009286

文献信息

• A Mild Procedure for the Lewis Acid-Catalyzed Ring-Opening of Activated Cyclopropanes with Amine Nucleophiles
  作者：Olga Lifchits、André B. Charette

  DOI：10.1021/ol8009286

  日期：2008.7.3

  The Lewis acid-catalyzed ring-opening of methyl 1-nitrocyclopropanecarboxylates with amine nucleophiles is described. The reaction proceeds at room temperature and with complete preservation of the enantiomeric purity from the electrophilic center of the cyclopropane to the acyclic product. The methodology was applied in an enantioselective synthesis of the dual serotonin/norepinephrine reuptake inhibitor (3R)-3-(1H-indol-1-yl)-N-methyl-3-phenylpropan-1-amine.
• Boronate Urea Activation of Nitrocyclopropane Carboxylates
  作者：Sonia S. So、Tyler J. Auvil、Victoria J. Garza、Anita E. Mattson

  DOI：10.1021/ol202873d

  日期：2012.1.20

  Boronate ureas operate as catalysts for the activation of nitrocyclopropane carboxylates in nucleophilic ring-opening reactions. A variety of amines were found to open the urea-activated nitrocyclopropane carboxylates, generating highly useful nitro ester building blocks In good yields. Standard manipulations allow access to a wide range of valuable compounds from the ring-opened products with direct applications in bioactive target synthesis.