Acetic acid (2aS,5aS,7S,7aS,10R,10aS,10bS,10cR)-10c-hydroxy-2a,4,4,7,10-pentamethyl-2,9-dioxo-dodecahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-7-yl ester | 776335-13-8

• 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: Acetic acid (2aS,5aS,7S,7aS,10R,10aS,10bS,10cR)-10c-hydroxy-2a,4,4,7,10-pentamethyl-2,9-dioxo-dodecahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-7-yl ester
• CAS: 776335-13-8
• 化学式: C₂₀H₂₈O₈
• 分子量: 396.438
• InChiKey: RVRXYDFFWRNQSE-AYDIXNHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2aS,5aS,7S,7aS,10R,10aS,10bS,10cR)-10c-hydroxy-2a,4,4,7,10-pentamethyl-2,9-dioxo-dodecahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-7-yl ester 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 2-deoctanoyl-4,5-dihydrothapsigargin
  参考文献：
  名称：

  Total Synthesis of Two Novel Subpicomolar Sarco/Endoplasmatic Reticulum Ca²⁺-ATPase Inhibitors Designed by an Analysis of the Binding Site of Thapsigargin

  摘要：

  Analysis of molecular interaction fields based on the published crystal structure of thapsigargin bound to the sarco/endoplasmatic reticulum Ca2+-ATPase and analysis of the volume and shape of the ligand binding site and of the SERCA-thapsigargin interactions have enabled design of two new compounds inhibiting SERCA in the subpicomolar range. The two inhibitors were synthesized using (S)-carvone as starting material and found to be 3 and 10 times more potent than thapsigargin.

  DOI：

  10.1021/jm058036v
• 作为产物：
  描述：

  乙酸酐 、 (1S,2S,3R,6S,7S,9S,13S,16R)-7,16-dihydroxy-3,7,11,11,13-pentamethyl-10,12,15-trioxatetracyclo[7.6.1.02,6.013,16]hexadecane-4,14-dione 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以89%的产率得到Acetic acid (2aS,5aS,7S,7aS,10R,10aS,10bS,10cR)-10c-hydroxy-2a,4,4,7,10-pentamethyl-2,9-dioxo-dodecahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-7-yl ester
  参考文献：
  名称：

  Total Synthesis of Two Novel Subpicomolar Sarco/Endoplasmatic Reticulum Ca²⁺-ATPase Inhibitors Designed by an Analysis of the Binding Site of Thapsigargin

  摘要：

  Analysis of molecular interaction fields based on the published crystal structure of thapsigargin bound to the sarco/endoplasmatic reticulum Ca2+-ATPase and analysis of the volume and shape of the ligand binding site and of the SERCA-thapsigargin interactions have enabled design of two new compounds inhibiting SERCA in the subpicomolar range. The two inhibitors were synthesized using (S)-carvone as starting material and found to be 3 and 10 times more potent than thapsigargin.

  DOI：

  10.1021/jm058036v