Phenyl-pyrrolidin-(2Z)-ylidene-acetic acid methyl ester | 33866-63-6

• 分子结构分类: 有机化合物
• 英文名称: Phenyl-pyrrolidin-(2Z)-ylidene-acetic acid methyl ester
• 英文别名: methyl (2Z)-2-phenyl-2-pyrrolidin-2-ylideneacetate
• CAS: 33866-63-6
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: MZDLGBQZDUVUGI-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Phenyl-pyrrolidin-(2Z)-ylidene-acetic acid methyl ester 在 platinum(IV) oxide 氢气 作用下， 以95%的产率得到(+/-)-erythro-methyl 2-phenyl-2-(2-azacyclopentyl)acetate
  参考文献：
  名称：

  The influence of the ring size of thiolactams in the Eschenmoser coupling reaction in presence of DBU. Formation of bicyclic thiazolidinones or thioimines

  摘要：

  The different behaviors of pyrrolidin-2-thione and piperidin-2-thione under a modified Eschenmoser sulfur contraction reaction protocol using DBU as base was observed. The pyrrolidin-2-thione lb follows the expected reaction course, leading to thioimines 5a-d. which can be transformed subsequently into the respective by action of a thiophile, while the piperidin-2-thione leads to the formation of bicyclic thiazolidinones 4b-d in moderate to good yields. The -enaminocarbonyl compound 11 was hydrogenated to afford the respective five-membered analogue of methylphenidate 12. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.049
• 作为产物：
  描述：

  methyl 2-((3,4-dihydro-2H-pyrrol-5-yl)thio)-2-phenylacetate hydrobromide 在 三乙胺 、 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 Phenyl-pyrrolidin-(2Z)-ylidene-acetic acid methyl ester
  参考文献：
  名称：

  Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

  摘要：

  The conditions of the Eschenmoser coupling reaction were studied. The formation of the alpha-thioiminium ion was achieved faster in the presence of an additive (Nal) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.081