methyl (1R,2S,5S,10S,14R,15R,22R,23R)-22-(hydroxymethyl)-1,2,8,8,15,22-hexamethyl-20-oxa-19-azahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-5-carboxylate | 1100749-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl (1R,2S,5S,10S,14R,15R,22R,23R)-22-(hydroxymethyl)-1,2,8,8,15,22-hexamethyl-20-oxa-19-azahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-5-carboxylate
• CAS: 1100749-72-1
• 化学式: C₃₂H₄₇NO₄
• 分子量: 509.729
• InChiKey: NLQBSYSUXTVQIY-QBKOHOJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1R,2S,5S,10S,14R,15R,22R,23R)-22-(hydroxymethyl)-1,2,8,8,15,22-hexamethyl-20-oxa-19-azahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-5-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Chemical modifications of natural triterpenes—glycyrrhetinic and boswellic acids: evaluation of their biological activity

  摘要：

  Synthetic analogues of naturally occurring triterpenoids: glycyrrhetinic acid, arjunolic acid, and boswellic acids, by modification of A-ring with a cyano- and enone-functionality, have been reported. A novel method of synthesis of alpha-cyanoenones from isoxazoles is reported. Bioassays using primary mouse macrophages and tumor cell lines indicate potent anti-inflammatory and cycotoxic activities associated with cyano-enones of boswellic acid and glycyrrhetinic acid. (C) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tet.2008.10.035
• 作为产物：
  描述：

  在 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 8.0h， 以146 mg的产率得到methyl (1R,2S,5S,10S,14R,15R,22R,23R)-22-(hydroxymethyl)-1,2,8,8,15,22-hexamethyl-20-oxa-19-azahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-5-carboxylate
  参考文献：
  名称：

  Chemical modifications of natural triterpenes—glycyrrhetinic and boswellic acids: evaluation of their biological activity

  摘要：

  Synthetic analogues of naturally occurring triterpenoids: glycyrrhetinic acid, arjunolic acid, and boswellic acids, by modification of A-ring with a cyano- and enone-functionality, have been reported. A novel method of synthesis of alpha-cyanoenones from isoxazoles is reported. Bioassays using primary mouse macrophages and tumor cell lines indicate potent anti-inflammatory and cycotoxic activities associated with cyano-enones of boswellic acid and glycyrrhetinic acid. (C) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tet.2008.10.035