1-methacryloyl-L-proline methyl ester | 53662-12-7

• 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: 1-methacryloyl-L-proline methyl ester
• 英文别名: 1-(Methacryloyl)prolin-methylester；methyl (2S)-1-(2-methylprop-2-enoyl)pyrrolidine-2-carboxylate
• CAS: 53662-12-7
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: ZXZFKAYHSJQDCX-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：

  1-methacryloyl-L-proline methyl ester 、 硫代乙酸 以 甲苯 为溶剂， 反应 40.0h， 以86%的产率得到1-(3'-acetylthio-2'-methylpropanoyl)-L-proline methyl ester
  参考文献：
  名称：

  Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries

  摘要：

  The conjugate addition of thioacetic acid to methacrylamides with chiral C-2-syrnmetric trans-2,5-disubstituted pyrrolidines afforded the addition products in excellent stereoselectivities (>99% de) and good yields (80-90%). The high selectivity was attributed mainly to the steric effect of the chiral auxiliaries. The cyclic nature of the chiral auxiliaries seemed also important for both the stereoselectivity and the reaction rate. Acidic hydrolysis of the adduct containing (2R,5R)-bis(methoxymethyl)pyrrotidine gave (S)-3-mercapto-2-methylpropanoic acid, a key intermediate for captopril, in 98% ee and 96% yield. The chiral auxiliary was recovered in the demethylated form of N-Boc-(2R,3R)-bis(hydroxymethyl)pyrrolidine in 90% yield. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.037
• 作为产物：
  描述：

  L-脯氨酸甲酯 、 甲基丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到1-methacryloyl-L-proline methyl ester
  参考文献：
  名称：

  Effenberger, Franz; Isak, Heinz, Chemische Berichte, 1989, vol. 122, p. 553 - 560

  摘要：

  DOI：

文献信息

• Effenberger, Franz; Isak, Heinz, Chemische Berichte, 1989, vol. 122, p. 553 - 560
  作者：Effenberger, Franz、Isak, Heinz

  DOI：——

  日期：——
• EFFENBERGER, FRANZ;ISAK, HEINZ, CHEM. BER., 122,(1989) N, C. 553-559
  作者：EFFENBERGER, FRANZ、ISAK, HEINZ

  DOI：——

  日期：——
• Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries
  作者：Byung Hyun Kim、Hee Bong Lee、Jae Kwang Hwang、Young Gyu Kim

  DOI：10.1016/j.tetasy.2005.01.037

  日期：2005.3

  The conjugate addition of thioacetic acid to methacrylamides with chiral C-2-syrnmetric trans-2,5-disubstituted pyrrolidines afforded the addition products in excellent stereoselectivities (>99% de) and good yields (80-90%). The high selectivity was attributed mainly to the steric effect of the chiral auxiliaries. The cyclic nature of the chiral auxiliaries seemed also important for both the stereoselectivity and the reaction rate. Acidic hydrolysis of the adduct containing (2R,5R)-bis(methoxymethyl)pyrrotidine gave (S)-3-mercapto-2-methylpropanoic acid, a key intermediate for captopril, in 98% ee and 96% yield. The chiral auxiliary was recovered in the demethylated form of N-Boc-(2R,3R)-bis(hydroxymethyl)pyrrolidine in 90% yield. (C) 2005 Elsevier Ltd. All rights reserved.