methyl (2E)-2-(1-benzylpyrrolidin-2-ylidene)propanoate | 1144516-33-5

• 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: methyl (2E)-2-(1-benzylpyrrolidin-2-ylidene)propanoate
• CAS: 1144516-33-5
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: DCSXRUQUNVBUFE-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2E)-2-(1-benzylpyrrolidin-2-ylidene)propanoate 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.5h， 以98%的产率得到
  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
• 作为产物：
  描述：

  1-benzyl-5-((1-methoxy-1-oxopropan-2-yl)thio)-3,4-dihydro-2H-pyrrol-1-ium bromide 在 三乙胺 、 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 methyl (2E)-2-(1-benzylpyrrolidin-2-ylidene)propanoate
  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

文献信息

• US7569589B2
  申请人：——

  公开号：US7569589B2

  公开（公告）日：2009-08-04
• Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids
  作者：Brenno A.D. Neto、Alexandre A.M. Lapis、Alinne B. Bernd、Dennis Russowsky

  DOI：10.1016/j.tet.2009.01.081

  日期：2009.3

  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.