colchinol hydrochloride | 84426-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: colchinol hydrochloride
• 英文别名: (aR,5S)-5-amino-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-3-ol hydrochloride；colchinol.HCl；(S)-5-amino-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-ol; hydrochloride；(S)-5-Amino-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-ol; Hydrochlorid
• CAS: 84426-30-2
• 化学式: C₁₈H₂₁NO₄*ClH
• 分子量: 351.83
• InChiKey: LHFQIPKGSHWSTJ-UQKRIMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.94
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  colchinol hydrochloride 在 copper(ll) sulfate pentahydrate 、 triflic azide 、 碳酸氢钠 、 sodium ascorbate 作用下， 以 甲醇 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 2.33h， 生成
  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 、 碘 、 potassium iodide 、 sodium hydroxide 、 锌 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 69.0h， 生成 colchinol hydrochloride
  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 synthesis of (aR,7S)-(−)-N-acetylcolchinol and its conjugate with a cyclic RGD peptide
  作者：Gilbert Besong、Denis Billen、Indu Dager、Philip Kocienski、Eric Sliwinski、Lik Ren Tai、F. Thomas Boyle

  DOI：10.1016/j.tet.2008.01.130

  日期：2008.5

  An asymmetric synthesis of (−)-N-acetylcolchinol is described based on a Suzuki–Miyaura coupling to generate the biaryl pharmacophore. The sole asymmetric centre was introduced by an asymmetric reduction of a dibenzosuberone derivative 24 using lithium borohydride in the presence of stoichiometric amounts of a chiral Lewis acid (TarB–NO2). A conjugate between an αVβ3 integrin-binding cyclic peptide

  基于Suzuki-Miyaura偶联生成联芳基药效团，描述了（-）- N-乙酰基胆酚的不对称合成。在化学计量的手性路易斯酸（TarB–NO 2）存在下，使用硼氢化锂通过不对称还原二苯并亚砜酮衍生物24引入了唯一的不对称中心。一个α之间的缀合物V β 3整联蛋白结合环肽C [RGDfK]和colchinol（己二酰接头）与一个目标合成以选择性地递送colchinol实体瘤。