(aR,5S)-5-azido-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-3-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (aR,5S)-5-azido-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-3-ol
• 英文别名: (8S)-8-azido-13,14,15-trimethoxytricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,11,13-hexaen-5-ol
• 化学式: C₁₈H₁₉N₃O₄
• 分子量: 341.367
• InChiKey: LTUFNJMSILYRNN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (aR,5S)-5-azido-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-3-ol 、 Lauric acid propargylic ester 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.33h， 以93%的产率得到
  参考文献：
  名称：

  A Convenient Entry to New C-7-Modified Colchicinoids through Azide Alkyne [3+2] Cycloaddition: Application of Ring-Contractive Rearrangements

  摘要：

  Reliable procedures for the preparation of azides derived from colchicine (1), allocolchicine (3) and N-acetylcolchinol (4a) were developed. These azides were then employed in Cu-catalyzed Huisgen-Sharpless [3+2] cycloaddition ("click") reactions with alkynes under microwave irradiation. The method developed opens a convenient and efficient access to libraries of new C-7-modified colchicinoids (triazole derivatives). In addition, a plausible mechanistic rationale for the colchicine-allocolchicine rearrangement is suggested.

  DOI：

  10.3987/com-10-s(e)117
• 作为产物：
  描述：

  秋水仙碱 在 盐酸 、 copper(ll) sulfate pentahydrate 、 triflic azide 、 碘 、 碳酸氢钠 、 potassium iodide 、 sodium hydroxide 、 锌 作用下， 以 甲醇 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 71.0h， 生成 (aR,5S)-5-azido-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-3-ol
  参考文献：
  名称：

  A Convenient Entry to New C-7-Modified Colchicinoids through Azide Alkyne [3+2] Cycloaddition: Application of Ring-Contractive Rearrangements

  摘要：

  Reliable procedures for the preparation of azides derived from colchicine (1), allocolchicine (3) and N-acetylcolchinol (4a) were developed. These azides were then employed in Cu-catalyzed Huisgen-Sharpless [3+2] cycloaddition ("click") reactions with alkynes under microwave irradiation. The method developed opens a convenient and efficient access to libraries of new C-7-modified colchicinoids (triazole derivatives). In addition, a plausible mechanistic rationale for the colchicine-allocolchicine rearrangement is suggested.

  DOI：

  10.3987/com-10-s(e)117

文献信息

• A Convenient Entry to New C-7-Modified Colchicinoids through Azide Alkyne [3+2] Cycloaddition: Application of Ring-Contractive Rearrangements
  作者：Hans-Günther Schmalz、Norman Nicolaus、Jens Reball、Nikolay Sitnikov、Alexey Yu. Fedorov、Janna Velder、Andreas Termath

  DOI：10.3987/com-10-s(e)117

  日期：——

  Reliable procedures for the preparation of azides derived from colchicine (1), allocolchicine (3) and N-acetylcolchinol (4a) were developed. These azides were then employed in Cu-catalyzed Huisgen-Sharpless [3+2] cycloaddition ("click") reactions with alkynes under microwave irradiation. The method developed opens a convenient and efficient access to libraries of new C-7-modified colchicinoids (triazole derivatives). In addition, a plausible mechanistic rationale for the colchicine-allocolchicine rearrangement is suggested.