(4S)-4-ethyl-5-(p-tolylsulfonyloxy)-4-(trimethylsilyloxy)pentanal | 360787-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S)-4-ethyl-5-(p-tolylsulfonyloxy)-4-(trimethylsilyloxy)pentanal
• 英文别名: [(2S)-2-ethyl-5-oxo-2-trimethylsilyloxypentyl] 4-methylbenzenesulfonate
• CAS: 360787-59-3
• 化学式: C₁₇H₂₈O₅SSi
• 分子量: 372.558
• InChiKey: BTKOHQZEURBRSQ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-ethyl-5-(p-tolylsulfonyloxy)-4-(trimethylsilyloxy)pentanal 、 methyl 3-benzyl-2,3,4,5,6,11-hexahydro-1H-azocino[4,5-b]indole-1-carboxylate 以 甲苯 为溶剂， 反应 18.0h， 以97%的产率得到methyl 4-benzyl-1,2,3,4,4a,5,6,8-octahydro-5-[(2S)-2-ethyl-2-[(trimethylsil)oxy]-3-[(p-tolylsulfonyl)oxy]propyl]pyrido[2,3-d]carbazole-7-carboxylate
  参考文献：
  名称：

  Syntheses of 5a‘-homo-Vinblastine and Congeners Designed to Establish Structural Determinants for Isolation of Atropisomers

  摘要：

  The syntheses of 5a'-homo-vinblastine (3a) and its C-20' methyl congener 62a were achieved. In contrast to vinblastine, these compounds did not allow isolation of atropisomers because of their lower conformational inversion barrier. However, annelation of a six-membered ring to the conformationally mobile D'-piperidine ring provided an isolated atropisomer 81a, which could be converted to its lower energy conformation 65a on heating. The 5a'-homo-vinblastine congeners 3a, 62a, and 65a showed vinblastine-like inhibition of tubulin polymerization and cytotoxicity to L1210 leukemia cells, albeit at lower potency for the latter activity, than that found with the corresponding compounds in the vinblastine series.

  DOI：

  10.1021/jo000249z
• 作为产物：
  描述：

  4-甲苯磺酸酐 在 4-二甲氨基吡啶 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.75h， 生成 (4S)-4-ethyl-5-(p-tolylsulfonyloxy)-4-(trimethylsilyloxy)pentanal
  参考文献：
  名称：

  Syntheses of 5a‘-homo-Vinblastine and Congeners Designed to Establish Structural Determinants for Isolation of Atropisomers

  摘要：

  The syntheses of 5a'-homo-vinblastine (3a) and its C-20' methyl congener 62a were achieved. In contrast to vinblastine, these compounds did not allow isolation of atropisomers because of their lower conformational inversion barrier. However, annelation of a six-membered ring to the conformationally mobile D'-piperidine ring provided an isolated atropisomer 81a, which could be converted to its lower energy conformation 65a on heating. The 5a'-homo-vinblastine congeners 3a, 62a, and 65a showed vinblastine-like inhibition of tubulin polymerization and cytotoxicity to L1210 leukemia cells, albeit at lower potency for the latter activity, than that found with the corresponding compounds in the vinblastine series.

  DOI：

  10.1021/jo000249z

文献信息

• Syntheses of 5a‘-<i>h</i><i>omo</i>-Vinblastine and Congeners Designed to Establish Structural Determinants for Isolation of Atropisomers
  作者：Martin E. Kuehne、Scott D. Cowen、Feng Xu、Linda S. Borman

  DOI：10.1021/jo000249z

  日期：2001.8.1

  The syntheses of 5a'-homo-vinblastine (3a) and its C-20' methyl congener 62a were achieved. In contrast to vinblastine, these compounds did not allow isolation of atropisomers because of their lower conformational inversion barrier. However, annelation of a six-membered ring to the conformationally mobile D'-piperidine ring provided an isolated atropisomer 81a, which could be converted to its lower energy conformation 65a on heating. The 5a'-homo-vinblastine congeners 3a, 62a, and 65a showed vinblastine-like inhibition of tubulin polymerization and cytotoxicity to L1210 leukemia cells, albeit at lower potency for the latter activity, than that found with the corresponding compounds in the vinblastine series.