(22R,23R) 3α-azido-22,23-dihydroxy-5α-stigmastan-6-one | 777864-01-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (22R,23R) 3α-azido-22,23-dihydroxy-5α-stigmastan-6-one
• 英文别名: (3R,5S,8S,9S,10R,13S,14S,17R)-3-azido-17-[(2S,3R,4R,5S)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 777864-01-4
• 化学式: C₂₉H₄₉N₃O₃
• 分子量: 487.726
• InChiKey: BASJSWZPSYWNEO-CRZFLPRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  71.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (22R,23R) 3α-azido-22,23-dihydroxy-5α-stigmastan-6-one 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 以65%的产率得到(22R,23R) 3α-amino-22,23-dihydroxy-5α-stigmastan-6-one
  参考文献：
  名称：

  New brassinosteroid analogs having nitrogenated functionalities at C3 to provide more information about the brassinosteroid–receptor interaction

  摘要：

  An efficient synthesis of different brassinosteroid derivatives with an azide or an amine function at C3 without any function at C2 and their biological activity evaluation in the rice lamina inclination test is described. The key step in the synthetic strategy involves a nucleophilic substitution by azide of an activated 3beta-OH followed by reduction to amine. The activity elicited by 7 and 9 having an azide group, in contrast with the residual ones elicited by their corresponding amines, suggests that the 3alpha-OH group of an active brassinosteroid could act as acceptor in the putative hydrogen bonding interaction with the receptor/s. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.126
• 作为产物：
  描述：

  (22E)-3β-hydroxystigmast-22-en-6-one 在 四乙基醋酸铵 四氧化锇 、 sodium azide 、 N-甲基吲哚酮 、 dihydroquinidine 0-O-(9'-phenanthryl) ether 、 TEA 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 285.0h， 生成 (22R,23R) 3α-azido-22,23-dihydroxy-5α-stigmastan-6-one
  参考文献：
  名称：

  New brassinosteroid analogs having nitrogenated functionalities at C3 to provide more information about the brassinosteroid–receptor interaction

  摘要：

  An efficient synthesis of different brassinosteroid derivatives with an azide or an amine function at C3 without any function at C2 and their biological activity evaluation in the rice lamina inclination test is described. The key step in the synthetic strategy involves a nucleophilic substitution by azide of an activated 3beta-OH followed by reduction to amine. The activity elicited by 7 and 9 having an azide group, in contrast with the residual ones elicited by their corresponding amines, suggests that the 3alpha-OH group of an active brassinosteroid could act as acceptor in the putative hydrogen bonding interaction with the receptor/s. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.126

文献信息

• New brassinosteroid analogs having nitrogenated functionalities at C3 to provide more information about the brassinosteroid–receptor interaction
  作者：Carme Brosa、Marc Amorós、Meritxell Molist、Xavier Hernàndez

  DOI：10.1016/j.tet.2004.06.126

  日期：2004.9

  An efficient synthesis of different brassinosteroid derivatives with an azide or an amine function at C3 without any function at C2 and their biological activity evaluation in the rice lamina inclination test is described. The key step in the synthetic strategy involves a nucleophilic substitution by azide of an activated 3beta-OH followed by reduction to amine. The activity elicited by 7 and 9 having an azide group, in contrast with the residual ones elicited by their corresponding amines, suggests that the 3alpha-OH group of an active brassinosteroid could act as acceptor in the putative hydrogen bonding interaction with the receptor/s. (C) 2004 Elsevier Ltd. All rights reserved.