(3R,5aS,6R,8aR,9R,10R,12R,12aR)-3,6,9-trimethyl-9-(methylsulfonyl)decahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-ol | 1037586-05-2

• 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: (3R,5aS,6R,8aR,9R,10R,12R,12aR)-3,6,9-trimethyl-9-(methylsulfonyl)decahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-ol
• CAS: 1037586-05-2
• 化学式: C₁₆H₂₆O₇S
• 分子量: 362.444
• InChiKey: MOPUFKZXHIEULB-GHUSENRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3R,5aS,6R,8aR,9R,10R,12R,12aR)-3,6,9-trimethyl-9-(methylsulfonyl)decahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-ol 、 4-正癸基苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以70%的产率得到(3R,5aS,6R,8aR,9R,10S,12R,12aR)-3,6,9-trimethyl-9-(methylsulfonyl)decahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl 4-decylbenzoate
  参考文献：
  名称：

  Electronically stabilized versions of the antimalarial acetal trioxanes artemether and artesunate

  摘要：

  From 9-substituted DHA, several new artemisinin-derived C-10 acetal ethers and esters were prepared with either a 9-fluoro or a 9-sulfonyl substituent. The very strong inductive electron-withdrawing C-9 substituent is shown to retard considerably C-10 ionization (acid-promoted etherification) of 9-fluoro-DHA and 9-sulfonyl-DHA. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.010
• 作为产物：
  描述：

  9-methanesulfonylartemisinin 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以87%的产率得到(3R,5aS,6R,8aR,9R,10R,12R,12aR)-3,6,9-trimethyl-9-(methylsulfonyl)decahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-ol
  参考文献：
  名称：

  Electronically stabilized versions of the antimalarial acetal trioxanes artemether and artesunate

  摘要：

  From 9-substituted DHA, several new artemisinin-derived C-10 acetal ethers and esters were prepared with either a 9-fluoro or a 9-sulfonyl substituent. The very strong inductive electron-withdrawing C-9 substituent is shown to retard considerably C-10 ionization (acid-promoted etherification) of 9-fluoro-DHA and 9-sulfonyl-DHA. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.010