(1S,3R,6S,8R,11S,12S,15R,16R)-15-[(2R)-6-hydroxy-6-methyl-5-phenylselanylheptan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol | 943985-75-9

• 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: (1S,3R,6S,8R,11S,12S,15R,16R)-15-[(2R)-6-hydroxy-6-methyl-5-phenylselanylheptan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol
• CAS: 943985-75-9
• 化学式: C₃₆H₅₆O₂Se
• 分子量: 599.799
• InChiKey: OWNDYHVMEXDWDO-HFGXQKCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.79
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3R,6S,8R,11S,12S,15R,16R)-15-[(2R)-6-hydroxy-6-methyl-5-phenylselanylheptan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol 在 吡啶 、 sodium periodate 、 四氧化锇 、 双氧水 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 26.0h， 生成 ethyl (E,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
• 作为产物：
  描述：

  环阿屯醇 在 sodium tetrahydroborate 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.17h， 生成 (1S,3R,6S,8R,11S,12S,15R,16R)-15-[(2R)-6-hydroxy-6-methyl-5-phenylselanylheptan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol
  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