methyl (E)-(N-acetylpyrrolidin-2-ylidene)acetate | 763105-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (E)-(N-acetylpyrrolidin-2-ylidene)acetate
• 英文别名: methyl (2E)-2-(1-acetylpyrrolidin-2-ylidene)acetate
• CAS: 763105-75-5
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: BMAGCBFAKUADLP-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-(N-acetylpyrrolidin-2-ylidene)acetate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate (S,S)-1,3-dimethyl-4,5-(Ph₂PCH₂)2-imidazolidin-2-one 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 12.0h， 生成 methyl 2-[(2R)-1-acetylpyrrolidin-2-yl]acetate
  参考文献：
  名称：

  Asymmetric synthesis of homoproline derivatives via Rh(I)-catalyzed hydrogenation using chiral bisphosphines as ligands

  摘要：

  It has been demonstrated for the first time that Rh(I)-catalyzed asymmetric hydrogenation of cyclic beta-enamino acid derivatives I using chiral bisphosphines could be a highly efficient synthetic method for optically active homoproline derivatives. The enantioselectivity and conversion yield were largely dependent upon the chiral ligand. Using the Me-BDPMI forming a seven-membered metal chelate, the N-acetylated beta-enamino acid methyl ester la was hydrogenated to give optically active homoproline derivative 2a with 100% conversion and 96% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.014
• 作为产物：
  描述：

  2-(Methoxycarbonylmethylene)pyrrolidine 、 乙酰氯 以 苯 为溶剂， 反应 3.0h， 以74%的产率得到methyl (E)-(N-acetylpyrrolidin-2-ylidene)acetate
  参考文献：
  名称：

  Asymmetric synthesis of homoproline derivatives via Rh(I)-catalyzed hydrogenation using chiral bisphosphines as ligands

  摘要：

  It has been demonstrated for the first time that Rh(I)-catalyzed asymmetric hydrogenation of cyclic beta-enamino acid derivatives I using chiral bisphosphines could be a highly efficient synthetic method for optically active homoproline derivatives. The enantioselectivity and conversion yield were largely dependent upon the chiral ligand. Using the Me-BDPMI forming a seven-membered metal chelate, the N-acetylated beta-enamino acid methyl ester la was hydrogenated to give optically active homoproline derivative 2a with 100% conversion and 96% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.014

文献信息

• Asymmetric synthesis of homoproline derivatives via Rh(I)-catalyzed hydrogenation using chiral bisphosphines as ligands
  作者：Yong Jian Zhang、Jung Hwan Park、Sang-gi Lee

  DOI：10.1016/j.tetasy.2004.04.014

  日期：2004.7

  It has been demonstrated for the first time that Rh(I)-catalyzed asymmetric hydrogenation of cyclic beta-enamino acid derivatives I using chiral bisphosphines could be a highly efficient synthetic method for optically active homoproline derivatives. The enantioselectivity and conversion yield were largely dependent upon the chiral ligand. Using the Me-BDPMI forming a seven-membered metal chelate, the N-acetylated beta-enamino acid methyl ester la was hydrogenated to give optically active homoproline derivative 2a with 100% conversion and 96% ee. (C) 2004 Elsevier Ltd. All rights reserved.