24,25-epoxycycloartanol | 26955-76-0

• 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: 24,25-epoxycycloartanol
• 英文别名: cycloartan-24,25-epoxy-3β-ol；24,25-epoxy-cycloartan-3-ol；(1S,3R,6S,8R,11S,12S,15R,16R)-15-[(2R)-4-(3,3-dimethyloxiran-2-yl)butan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol
• CAS: 26955-76-0
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: AAXMYXKQQLLBQO-SOEWQUOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  24,25-epoxycycloartanol 在 吡啶 、 sodium tetrahydroborate 、 双氧水 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 (23E)-25-hydroxycycloart-23-ene-3β,25-diol
  参考文献：
  名称：

  Structural Revision of Terpenoids with a (3Z)-2-Methyl-3-penten-2-ol Moiety by the Synthesis of (23E)- and (23Z)-Cycloart-23-ene-3β,25-diols

  摘要：

  Synthesis of (23E)-cycloart-23-ene-3 beta,25-diol (1) and its 23Z-isomer 2 was achieved by using cycloartenol as a starting material, thus revising the proposed structure of natural 2 to 1 unequivocally. These synthetic studies revealed that the structural revision (Z-form -> E-form) should also be applied to terpenoids such as (23Z)-3 beta-acetoxyeupha-7,23-diene-25-ol, (23Z)-tirucalla-7,23-diene-3 beta,25-diol, quadrangularol A, quadrangularic acid K, and daurichromene C.

  DOI：

  10.1021/jo070478m
• 作为产物：
  描述：

  环阿屯醇 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以87%的产率得到24,25-epoxycycloartanol
  参考文献：
  名称：

  Structural Revision of Terpenoids with a (3Z)-2-Methyl-3-penten-2-ol Moiety by the Synthesis of (23E)- and (23Z)-Cycloart-23-ene-3β,25-diols

  摘要：

  Synthesis of (23E)-cycloart-23-ene-3 beta,25-diol (1) and its 23Z-isomer 2 was achieved by using cycloartenol as a starting material, thus revising the proposed structure of natural 2 to 1 unequivocally. These synthetic studies revealed that the structural revision (Z-form -> E-form) should also be applied to terpenoids such as (23Z)-3 beta-acetoxyeupha-7,23-diene-25-ol, (23Z)-tirucalla-7,23-diene-3 beta,25-diol, quadrangularol A, quadrangularic acid K, and daurichromene C.

  DOI：

  10.1021/jo070478m

文献信息

• Structural Revision of Terpenoids with a (3<i>Z</i>)-2-Methyl-3-penten-2-ol Moiety by the Synthesis of (23<i>E</i>)- and (23<i>Z</i>)-Cycloart-23-ene-3β,25-diols
  作者：Shunya Takahashi、Hiroko Satoh、Yayoi Hongo、Hiroyuki Koshino

  DOI：10.1021/jo070478m

  日期：2007.6.1

  Synthesis of (23E)-cycloart-23-ene-3 beta,25-diol (1) and its 23Z-isomer 2 was achieved by using cycloartenol as a starting material, thus revising the proposed structure of natural 2 to 1 unequivocally. These synthetic studies revealed that the structural revision (Z-form -> E-form) should also be applied to terpenoids such as (23Z)-3 beta-acetoxyeupha-7,23-diene-25-ol, (23Z)-tirucalla-7,23-diene-3 beta,25-diol, quadrangularol A, quadrangularic acid K, and daurichromene C.