(10R,11S,12S)-12-羟基-4,6,6,10,11-五甲基-11,12-二氢-2H,6H,10H-二吡喃并[2,3-f:2',3'-h]色烯-2-酮 | 98449-39-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: (10R,11S,12S)-12-羟基-4,6,6,10,11-五甲基-11,12-二氢-2H,6H,10H-二吡喃并[2,3-f:2',3'-h]色烯-2-酮
• 英文名称: (+)-cordatolide A
• 英文别名: cordatolide A；(16R,17S,18S)-18-hydroxy-6,10,10,16,17-pentamethyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaen-4-one
• CAS: 98449-39-9
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: VFKOXOKVQKGOTG-UVWXRNBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (10R,11S,12S)-12-羟基-4,6,6,10,11-五甲基-11,12-二氢-2H,6H,10H-二吡喃并[2,3-f:2',3'-h]色烯-2-酮 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以0.03 g的产率得到deoxydihydrocordatolide
  参考文献：
  名称：

  Triterpenoids and coumarins from the leaves of calophyllum cordato-oblongum

  摘要：

  DOI：

  10.1016/s0031-9422(00)81064-x
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以23%的产率得到(10R,11S,12S)-12-羟基-4,6,6,10,11-五甲基-11,12-二氢-2H,6H,10H-二吡喃并[2,3-f:2',3'-h]色烯-2-酮
  参考文献：
  名称：

  Chemical resolution of (±)-calanolide A, (±)-cordatolide A and their 11-demethyl analogues

  摘要：

  The chemical resolution of (+/-)-calanolide A and (+/-)-cordatolide A into their corresponding optically active enantiomers is described. Their inhibitory activities against HIV-1 are tested in vitro. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.008

文献信息

• New methylethers of cordatolides from <i>Calophyllum cordato-oblongum</i> and their synthesis
  作者：H.R.W. Dharmaratne、G.P.K. Marasinghe

  DOI：10.1080/14786410600906046

  日期：2009.7.10

  Twigs of Calophyllum cordato-oblongum Thw. have been shown to contain cordatolide A-OMe, cordatolide B-OMe, cordatolide C-OMe, cordatolide A, cordatolide B, oblongulide, cordatooblongic acid, friedelin, canophyllol, and sitosterol. Methylation of cordatolide B and the attempted methylation of cordatolide A under acidic conditions gave cordatolide B-OMe and 11,12-anhydrocordatolide. Cordatolide A-OMe, cordatolide C-OMe and 11,12-anhydrocordatolide are new compounds.
• Chemical resolution of (±)-calanolide A, (±)-cordatolide A and their 11-demethyl analogues
  作者：Tao Ma、Qi Gao、Zhiwei Chen、Lin Wang、Gang Liu

  DOI：10.1016/j.bmcl.2007.12.008

  日期：2008.2

  The chemical resolution of (+/-)-calanolide A and (+/-)-cordatolide A into their corresponding optically active enantiomers is described. Their inhibitory activities against HIV-1 are tested in vitro. (C) 2007 Elsevier Ltd. All rights reserved.
• Triterpenoids and coumarins from the leaves of calophyllum cordato-oblongum
  作者：H. Ranjith、W. Dharmaratne、Subramaniam Sotheeswaran、Sinnathamby Balasubramaniam、Eric S. Waight

  DOI：10.1016/s0031-9422(00)81064-x

  日期：1985.1