11-Hydroxy-3-((S)-1-hydroxy-3,3-dimethyl-butyl)-4-methoxy-9-methyl-7H-6,12-dioxa-dibenzo[a,d]cycloocten-5-one | 861405-80-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11-Hydroxy-3-((S)-1-hydroxy-3,3-dimethyl-butyl)-4-methoxy-9-methyl-7H-6,12-dioxa-dibenzo[a,d]cycloocten-5-one
• 英文别名: 6-hydroxy-2-[(1S)-1-hydroxy-3,3-dimethylbutyl]-1-methoxy-8-methyl-10H-benzo[b][1,5]benzodioxocin-12-one
• CAS: 861405-80-3
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: PQKUCALGIMRTHD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  11-Hydroxy-3-((S)-1-hydroxy-3,3-dimethyl-butyl)-4-methoxy-9-methyl-7H-6,12-dioxa-dibenzo[a,d]cycloocten-5-one 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-氯代丁二酰亚胺 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 三氯化铁 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 16.0h， 生成 8-Chloro-10-ethyl-11-hydroxy-3-((S)-1-hydroxy-3,3-dimethyl-butyl)-4-methoxy-9-methyl-7H-6,12-dioxa-dibenzo[a,d]cycloocten-5-one
  参考文献：
  名称：

  Dibenzodioxocinones—A new class of CETP inhibitors

  摘要：

  Derivatives of the natural product 11-hydroxy-3-[(S)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one 1 were studied as novel CETP inhibitors. Compound 2 was identified from HTS as a micromolar inhibitor. The compound suffered from very low stability in plasma. Optimisation by partial synthesis started from 1 and led to low-nanomolar inhibitors with good stability in rat plasma. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.073
• 作为产物：
  描述：

  3-((S)-1-Hydroxy-3-methyl-butyl)-4-methoxy-9-methyl-11-(3-methyl-butoxy)-7H-6,12-dioxa-dibenzo[a,d]cycloocten-5-one 在 sodium periodate 、 四氧化锇 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 为溶剂， 反应 6.5h， 生成 11-Hydroxy-3-((S)-1-hydroxy-3,3-dimethyl-butyl)-4-methoxy-9-methyl-7H-6,12-dioxa-dibenzo[a,d]cycloocten-5-one
  参考文献：
  名称：

  Dibenzodioxocinones—A new class of CETP inhibitors

  摘要：

  Derivatives of the natural product 11-hydroxy-3-[(S)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one 1 were studied as novel CETP inhibitors. Compound 2 was identified from HTS as a micromolar inhibitor. The compound suffered from very low stability in plasma. Optimisation by partial synthesis started from 1 and led to low-nanomolar inhibitors with good stability in rat plasma. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.073