ethyl (Z,5R)-5-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]hex-2-enoate | 943985-79-3

• 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: ethyl (Z,5R)-5-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]hex-2-enoate
• CAS: 943985-79-3
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: JUHXHSVARPSQIJ-ZAWSAPDZSA-N

物化性质

• 沸点：
  536.5±23.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (Z,5R)-5-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]hex-2-enoate 、 甲基锂 以 乙醚 为溶剂， 反应 2.5h， 以94%的产率得到cycloart-23Z-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：

  (23E)-25-hydroxycycloart-23-ene-3β,25-diol 在 sodium periodate 、 四氧化锇 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 13.0h， 生成 ethyl (Z,5R)-5-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]hex-2-enoate
  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