cyano-[1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-4-pentyl-piperidin-4-yl]-acetic acid ethyl ester | 863220-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: cyano-[1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-4-pentyl-piperidin-4-yl]-acetic acid ethyl ester
• 英文别名: Ethyl 2-cyano-2-[1-[(2,2,5,7,8-pentamethyl-3,4-dihydrochromen-6-yl)sulfonyl]-4-pentylpiperidin-4-yl]acetate
• CAS: 863220-09-1
• 化学式: C₂₉H₄₄N₂O₅S
• 分子量: 532.745
• InChiKey: NTVZLSIWEYCFER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  cyano-[1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-4-pentyl-piperidin-4-yl]-acetic acid ethyl ester 在 氢氧化钾 作用下， 以 乙二醇 为溶剂， 以81%的产率得到[1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-4-n-pentyl-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：

  4-羟基哌啶 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 cyano-[1-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-4-pentyl-piperidin-4-yl]-acetic 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.