Ethyl (2S,4S,5R)-4-benzyl-5-butylprolinate | 166757-32-0

• 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: Ethyl (2S,4S,5R)-4-benzyl-5-butylprolinate
• 英文别名: ethyl (2S,4S,5R)-4-benzyl-5-butylpyrrolidine-2-carboxylate
• CAS: 166757-32-0
• 化学式: C₁₈H₂₇NO₂
• 分子量: 289.418
• InChiKey: JNIOOIGKIWQIPN-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-辛醇 、 Ethyl (2S,4S,5R)-4-benzyl-5-butylprolinate 在 盐酸 作用下， 反应 0.5h， 生成 (2'S)-2'-Octyl (2S,4S,5R)-4-benzyl-5-butylprolinate
  参考文献：
  名称：

  Stereoselective Addition of Grignard-Derived Organocopper Reagents to N-Acyliminium Ions: Synthesis of Enantiopure 5- and 4,5-Substituted Prolinates

  摘要：

  Alkylation of nonracemic N-acyliminium ions derived from proline and 4-substituted prolines has been extended to different types of Grignard-derived organocopper reagents. The reaction proceeds with high yield and stereoselectivity to yield 5-mono- and 4,5-disubstituted prolinates. The stereochemistry is controlled by the formation of a RCu-pi complex intermediate between the N-acyliminium ion, the carbonyl group of the ester, and the copper species.

  DOI：

  10.1021/jo00121a020
• 作为产物：
  描述：

  ethyl (2S,4S)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate 在 copper(I) bromide dimethylsulfide complex 、 三氟化硼乙醚 、 双氧水 、 三乙基硼氢化锂 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.33h， 生成 Ethyl (2S,4S,5R)-4-benzyl-5-butylprolinate
  参考文献：
  名称：

  Stereoselective Addition of Grignard-Derived Organocopper Reagents to N-Acyliminium Ions: Synthesis of Enantiopure 5- and 4,5-Substituted Prolinates

  摘要：

  Alkylation of nonracemic N-acyliminium ions derived from proline and 4-substituted prolines has been extended to different types of Grignard-derived organocopper reagents. The reaction proceeds with high yield and stereoselectivity to yield 5-mono- and 4,5-disubstituted prolinates. The stereochemistry is controlled by the formation of a RCu-pi complex intermediate between the N-acyliminium ion, the carbonyl group of the ester, and the copper species.

  DOI：

  10.1021/jo00121a020

文献信息

• Stereoselective Addition of Grignard-Derived Organocopper Reagents to N-Acyliminium Ions: Synthesis of Enantiopure 5- and 4,5-Substituted Prolinates
  作者：Ivan Collado、Jesus Ezquerra、Concepcion Pedregal

  DOI：10.1021/jo00121a020

  日期：1995.8

  Alkylation of nonracemic N-acyliminium ions derived from proline and 4-substituted prolines has been extended to different types of Grignard-derived organocopper reagents. The reaction proceeds with high yield and stereoselectivity to yield 5-mono- and 4,5-disubstituted prolinates. The stereochemistry is controlled by the formation of a RCu-pi complex intermediate between the N-acyliminium ion, the carbonyl group of the ester, and the copper species.