ethyl N-acetylpyrrolidin-2-ylideneacetate | 87273-77-6

• 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: ethyl N-acetylpyrrolidin-2-ylideneacetate
• 英文别名: ethyl (2E)-2-(1-acetylpyrrolidin-2-ylidene)acetate
• CAS: 87273-77-6
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: BEGCWIWZGWIPKC-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  ethyl N-acetylpyrrolidin-2-ylideneacetate 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 ((R)-1-Acetyl-pyrrolidin-2-yl)-acetic acid ethyl ester
  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：

  α-(Tetrahydropyrrolylidene-2) acetate d'ethyle 、 乙酸酐 以99%的产率得到
  参考文献：
  名称：

  NAGASAKA, TATSUO;INOUE, HITOSHI;HAMAGUCHI, FUMIKO, HETEROCYCLES, 1983, 20, N 6, 1099-1107

  摘要：

  DOI：

文献信息

• An Efficient Synthesis of Chiral Cyclic β-Amino Acids via Asymmetric Hydrogenation
  作者：Cyrille Pousset、Marc Larchevêque、Roland Callens、Angela Marinetti

  DOI：10.1055/s-2004-835659

  日期：——

  Cyclic p-amino acids, homoproline, homopipecolic acid and 3-carboxy-methylmorpholine were obtained in high enantiomeric excesses by transition metal-catalyzed asymmetric hydrogenation of cyclic β-acylamino-alkenoates. These compounds were synthesized by a thio-Wittig reaction on N-protected thiolactames.

  通过过渡金属催化的环状β-酰基氨基-烯酸酯的不对称氢化，以高对映体过量获得环状p-氨基酸、高脯氨酸、高哌啶酸和3-羧基-甲基吗啉。这些化合物是通过在 N 保护的硫代内酰胺上的硫代-维蒂希反应合成的。
• Brunerie, Pascal; Celerier, Jean-Pierre; Petit, Huguette, Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1183 - 1188
  作者：Brunerie, Pascal、Celerier, Jean-Pierre、Petit, Huguette、Lhommet, Gerard

  DOI：——

  日期：——
• Nagasaka, Tatsuo; Inoue, Hitoshi; Hamaguchi, Fumiko, Heterocycles, 1983, vol. 20, # 6, p. 1099 - 1107
  作者：Nagasaka, Tatsuo、Inoue, Hitoshi、Hamaguchi, Fumiko

  DOI：——

  日期：——
• BAHAJI EL HOUSSAIN; REFOUVELET B.; COUQUELET J.; TRONCHE P., C. R. ACAD. SCI., 303,(1986) N 6, 455-458
  作者：BAHAJI EL HOUSSAIN、 REFOUVELET B.、 COUQUELET J.、 TRONCHE P.

  DOI：——

  日期：——
• 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.