(2S,5S)-1-Benzylpyrrolidine-2,5-dicarboxylic acid | 93713-33-8

• 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: (2S,5S)-1-Benzylpyrrolidine-2,5-dicarboxylic acid
• 英文别名: (-)-N-benzylpyrrolidine-2,5-dicarboxylic acid；trans-1-Benzylpyrrolidine-2,5-dicarboxylic acid
• CAS: 93713-33-8
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: QREMUNONTQIPQO-QWRGUYRKSA-N

物化性质

• 沸点：
  460.0±45.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5S)-1-Benzylpyrrolidine-2,5-dicarboxylic acid 在 10percent P/C 氯化亚砜 、 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 40.0 ℃ 、344.73 kPa 条件下， 反应 82.0h， 生成 (2S,5S)-1-(tert-Butoxycarbonyl)pyrrolidine-2,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Studies of N-terminal templates for .alpha.-helix formation. Synthesis and conformational analysis of (2S,5S,8S,11S)-1-acetyl-1,4-diaza-3-keto-5-carboxy-10-thiatricyclo[2.8.1.04,8]tridecane (Ac-Hel1-OH)

  摘要：

  A convergent synthesis of the title compound, a conformationally restricted analogue of acetyl-L-prolyl-L-proline, from 1-acetyl-2(S)-carboxy-4(S)-mercaptopyrrolidine and trans-1-(tert-butoxycarbonyl)-2(S)-(methoxy-carbonyl)-5(S)-[(tosyloxy)methyl]pyrrolidine (Ac-Hel1-OH) is reported, along with a synthesis of (2S,8S,11S)-1-acetyl-1,4-diaza-3-keto-10-thiatricyclo[2.8.0(4,8)]tridecane. In the crystal and in CDCl3 solution the conformation of Ac-Hel1-OH is shown to approximate a staggered orientation at the 8,9-CC bond and an s-cis orientation at the acetyl amide bond. In DMF, DMSO, MeCN, and D2O significant amounts of the s-trans conformer are also present.

  DOI：

  10.1021/jo00023a037
• 作为产物：
  描述：

  trans-N-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 8.0h， 生成 (2S,5S)-1-Benzylpyrrolidine-2,5-dicarboxylic acid
  参考文献：
  名称：

  Studies of N-terminal templates for .alpha.-helix formation. Synthesis and conformational analysis of (2S,5S,8S,11S)-1-acetyl-1,4-diaza-3-keto-5-carboxy-10-thiatricyclo[2.8.1.04,8]tridecane (Ac-Hel1-OH)

  摘要：

  A convergent synthesis of the title compound, a conformationally restricted analogue of acetyl-L-prolyl-L-proline, from 1-acetyl-2(S)-carboxy-4(S)-mercaptopyrrolidine and trans-1-(tert-butoxycarbonyl)-2(S)-(methoxy-carbonyl)-5(S)-[(tosyloxy)methyl]pyrrolidine (Ac-Hel1-OH) is reported, along with a synthesis of (2S,8S,11S)-1-acetyl-1,4-diaza-3-keto-10-thiatricyclo[2.8.0(4,8)]tridecane. In the crystal and in CDCl3 solution the conformation of Ac-Hel1-OH is shown to approximate a staggered orientation at the 8,9-CC bond and an s-cis orientation at the acetyl amide bond. In DMF, DMSO, MeCN, and D2O significant amounts of the s-trans conformer are also present.

  DOI：

  10.1021/jo00023a037

文献信息

• Enzymes and catalysts. I. Pig liver esterase-catalyzed hydrolysis of heterocycli diesters.
  作者：YOSHIHISA MORIMOTO、YOSHIYASU TERAO、KAZUO ACHIWA

  DOI：10.1248/cpb.35.2266

  日期：——

  The asymmetric hydrolysis of five-membered cyclic diesters was carried out by using pig liver esterase (PLE) as a catalyst. The absolute configurations of the resulting half esters and recovered diesters were established and the stereospecificity of PLE action in such systems was revealed.

  五元环二酯的不对称水解是通过使用猪肝酯酶（PLE）作为催化剂进行的。得到的半酯和回收的二酯的绝对构型被确立，并揭示了PLE在此类体系中的立体特异性。
• Studies of N-terminal templates for .alpha.-helix formation. Synthesis and conformational analysis of (2S,5S,8S,11S)-1-acetyl-1,4-diaza-3-keto-5-carboxy-10-thiatricyclo[2.8.1.04,8]tridecane (Ac-Hel1-OH)
  作者：D. S. Kemp、Timothy P. Curran、William M. Davis、James G. Boyd、Christopher Muendel

  DOI：10.1021/jo00023a037

  日期：1991.11

  A convergent synthesis of the title compound, a conformationally restricted analogue of acetyl-L-prolyl-L-proline, from 1-acetyl-2(S)-carboxy-4(S)-mercaptopyrrolidine and trans-1-(tert-butoxycarbonyl)-2(S)-(methoxy-carbonyl)-5(S)-[(tosyloxy)methyl]pyrrolidine (Ac-Hel1-OH) is reported, along with a synthesis of (2S,8S,11S)-1-acetyl-1,4-diaza-3-keto-10-thiatricyclo[2.8.0(4,8)]tridecane. In the crystal and in CDCl3 solution the conformation of Ac-Hel1-OH is shown to approximate a staggered orientation at the 8,9-CC bond and an s-cis orientation at the acetyl amide bond. In DMF, DMSO, MeCN, and D2O significant amounts of the s-trans conformer are also present.