(5R,8S,8aS)-5-((S)-2-Hydroxy-1-methyl-ethyl)-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydro-azulen-2-ol | 399572-77-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5R,8S,8aS)-5-((S)-2-Hydroxy-1-methyl-ethyl)-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydro-azulen-2-ol
• CAS: 399572-77-1
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: YZYFBFQEAFBNGS-DPLHUVMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (5R,8S,8aS)-5-((S)-2-Hydroxy-1-methyl-ethyl)-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydro-azulen-2-ol 在 manganese(IV) oxide 、 三丁基膦 、 mercury(II) diacetate 、 双氧水 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 30.17h， 生成 hydrocolorenone
  参考文献：
  名称：

  Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin

  摘要：

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00986-3
• 作为产物：
  描述：

  3-oxo-1,7,10αH,6,11βH-guai-4-en-6,12-olide 在 lithium aluminium tetrahydride 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 3.25h， 生成 (5R,8S,8aS)-5-((S)-2-Hydroxy-1-methyl-ethyl)-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydro-azulen-2-ol
  参考文献：
  名称：

  Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin

  摘要：

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00986-3