trans-1-(tert-Butoxycarbonyl)-2-carboxy-5-(ethoxycarbonyl)pyrroldine | 136201-47-3

• 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: trans-1-(tert-Butoxycarbonyl)-2-carboxy-5-(ethoxycarbonyl)pyrroldine
• CAS: 136201-47-3
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: ZKEHIVOFKXKDQN-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  93.14
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  trans-1-(tert-Butoxycarbonyl)-2-carboxy-5-(ethoxycarbonyl)pyrroldine 在 4-二甲氨基吡啶 吡啶 、 sodium hydroxide 、 锂硼氢 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 61.67h， 生成 (2S,5S,8S,11S)-1-Acetyl-1,4-diaza-3-keto-5-carboxy-10-thiatricyclo<2.8.1.0^4,8>tridecane
  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：

  racemic trans-2,5-diethoxycarbonyl pyrrolidine 在 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 132.0h， 生成 trans-1-(tert-Butoxycarbonyl)-2-carboxy-5-(ethoxycarbonyl)pyrroldine
  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

• 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.