[4-benzyl-1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-piperidin-4-yl]-cyanoacetic acid ethyl ester | 863219-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [4-benzyl-1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-piperidin-4-yl]-cyanoacetic acid ethyl ester
• 英文别名: Ethyl 2-[4-benzyl-1-[(2,2,5,7,8-pentamethyl-3,4-dihydrochromen-6-yl)sulfonyl]piperidin-4-yl]-2-cyanoacetate
• CAS: 863219-88-9
• 化学式: C₃₁H₄₀N₂O₅S
• 分子量: 552.735
• InChiKey: TYOQLFXULRNZTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [4-benzyl-1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-piperidin-4-yl]-cyanoacetic acid ethyl ester 在 氢氧化钾 作用下， 以 乙二醇 为溶剂， 反应 4.0h， 以80%的产率得到[4-benzyl-1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-piperidin-4-yl]-acetic acid
  参考文献：
  名称：

  Application of the PMC Protecting Group in the Efficient Synthesis of 4,4‐Disubstituted Piperidines

  摘要：

  An efficient synthesis of the 4,4-disubstituted piperidine scaffold 1 was accomplished by treating the PMC N-protected alpha,beta-unsaturated ethyl cyanoacetate 9 with various Grignard reagents (R1MgX). Subsequent heating at 190 degrees C in a strong base provided carboxylic acids 12-20b in good yield. The PMC group was easily removed at room temperature with 33% HBr in acetic acid.

  DOI：

  10.1081/scc-200061570
• 作为产物：
  描述：

  2,2,5,7,8-五甲基苯并二氢吡喃-6-磺酰氯 在 乙酸铵 、 四丙基高钌酸铵 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 [4-benzyl-1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-piperidin-4-yl]-cyanoacetic acid ethyl ester
  参考文献：
  名称：

  Application of the PMC Protecting Group in the Efficient Synthesis of 4,4‐Disubstituted Piperidines

  摘要：

  An efficient synthesis of the 4,4-disubstituted piperidine scaffold 1 was accomplished by treating the PMC N-protected alpha,beta-unsaturated ethyl cyanoacetate 9 with various Grignard reagents (R1MgX). Subsequent heating at 190 degrees C in a strong base provided carboxylic acids 12-20b in good yield. The PMC group was easily removed at room temperature with 33% HBr in acetic acid.

  DOI：

  10.1081/scc-200061570

文献信息

• Application of the PMC Protecting Group in the Efficient Synthesis of 4,4‐Disubstituted Piperidines
  作者：Janet L. Ralbovsky、Joseph G. Lisko、Wei He

  DOI：10.1081/scc-200061570

  日期：2005.6.1

  An efficient synthesis of the 4,4-disubstituted piperidine scaffold 1 was accomplished by treating the PMC N-protected alpha,beta-unsaturated ethyl cyanoacetate 9 with various Grignard reagents (R1MgX). Subsequent heating at 190 degrees C in a strong base provided carboxylic acids 12-20b in good yield. The PMC group was easily removed at room temperature with 33% HBr in acetic acid.