10-ethylsulfinylcolchicide | 119681-81-1

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 10-ethylsulfinylcolchicide
• 英文别名: N-[10-(ethanesulfinyl)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl]-acetamide；N-[10-(Aethansulfinyl)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl]-acetamid；N-[(7S)-10-ethylsulfinyl-1,2,3-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS: 119681-81-1；119681-82-2
• 化学式: C₂₃H₂₇NO₆S
• 分子量: 445.536
• InChiKey: QVGVXKFHNFOZOJ-AUBGMPCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  哌啶 、 10-ethylsulfinylcolchicide 以 二甲基亚砜 为溶剂， 生成 N-[(7S)-1,2,3-trimethoxy-9-oxo-10-(piperidin-1-yl)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
  参考文献：
  名称：

  ipso-vs. tele-Nucleophilic substitution by piperidine on isocolchicides and colchicides bearing an α-leaving group

  摘要：

  Product studies of the reactions of piperidine with colchicides carrying a C-10 nucleofugic group show that only ipso substitution occurs. For isocolchicides carrying an X nucleofugic group at C-9, similar behaviour was observed for X = F, OTs or OMe, while for X = SMe, SOMe or Cl tele substitution (at C-ll) competes with ipso substitution. These results together with the observation that the reaction rates for the two series are similar, may be useful in guiding the refunctionalization of similar compounds.

  DOI：

  10.1039/p19950002657
• 作为产物：
  描述：

  10-ethylthiocolchicide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到10-ethylsulfinylcolchicide
  参考文献：
  名称：

  ipso-vs. tele-Nucleophilic substitution by piperidine on isocolchicides and colchicides bearing an α-leaving group

  摘要：

  Product studies of the reactions of piperidine with colchicides carrying a C-10 nucleofugic group show that only ipso substitution occurs. For isocolchicides carrying an X nucleofugic group at C-9, similar behaviour was observed for X = F, OTs or OMe, while for X = SMe, SOMe or Cl tele substitution (at C-ll) competes with ipso substitution. These results together with the observation that the reaction rates for the two series are similar, may be useful in guiding the refunctionalization of similar compounds.

  DOI：

  10.1039/p19950002657

文献信息

• Velluz; Muller, Bulletin de la Societe Chimique de France, 1954, p. 194,195
  作者：Velluz、Muller

  DOI：——

  日期：——
• ipso-vs. tele-Nucleophilic substitution by piperidine on isocolchicides and colchicides bearing an α-leaving group
  作者：Marino Cavazza、Francesco Pietra

  DOI：10.1039/p19950002657

  日期：——

  Product studies of the reactions of piperidine with colchicides carrying a C-10 nucleofugic group show that only ipso substitution occurs. For isocolchicides carrying an X nucleofugic group at C-9, similar behaviour was observed for X = F, OTs or OMe, while for X = SMe, SOMe or Cl tele substitution (at C-ll) competes with ipso substitution. These results together with the observation that the reaction rates for the two series are similar, may be useful in guiding the refunctionalization of similar compounds.