(6aR,10aR)-9-(1,3-dithian-2-yl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol | 123408-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (6aR,10aR)-9-(1,3-dithian-2-yl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 123408-92-4
• 化学式: C₂₄H₃₄O₂S₂
• 分子量: 418.665
• InChiKey: CRCKOYFWUKEQTF-RTBURBONSA-N

物化性质

• 沸点：
  519.2±50.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (6aR,10aR)-9-(1,3-dithian-2-yl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol 在 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 11-oxo-6a,10a-trans-Δ⁹-THC
  参考文献：
  名称：

  Synthesis of racemic and optically active .DELTA.9-tetrahydrocannabinol (THC) metabolites

  摘要：

  The preparation of racemic and optically active DELTA-9-THC metabolites is described from synthon 13. Racemic synthon 13 is prepared in four steps (46%) from Danishefsky's diene. Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23% yield). Alternatively, nopinone can be converted to 13 in three steps (50% yield) via a cyclobutane ring cleavage. The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl DELTA-9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4b from 5-(1',1'-dimethylheptyl)resorcinol (6c).

  DOI：

  10.1021/jo00024a031
• 作为产物：
  描述：

  (+/-)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enone 在 正丁基锂 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.25h， 生成 (6aR,10aR)-9-(1,3-dithian-2-yl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
  参考文献：
  名称：

  Synthesis of racemic and optically active .DELTA.9-tetrahydrocannabinol (THC) metabolites

  摘要：

  The preparation of racemic and optically active DELTA-9-THC metabolites is described from synthon 13. Racemic synthon 13 is prepared in four steps (46%) from Danishefsky's diene. Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23% yield). Alternatively, nopinone can be converted to 13 in three steps (50% yield) via a cyclobutane ring cleavage. The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl DELTA-9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4b from 5-(1',1'-dimethylheptyl)resorcinol (6c).

  DOI：

  10.1021/jo00024a031

文献信息

• [EN] TETRAHYDROCANNABINOID- PROTEIN CONJUGATES FOR THE PRODUCTION OF ANTIBODIES FOR THE DETECTION OF T?TRAHYDROCANNABINOID COMPONENTS IN SALIVA<br/>[FR] ANTIGENES TETRAHYDROCANNABINOIDES ET LEUR PROCEDE D'UTILISATION
  申请人：OAKVILLE HONG KONG COMPANY LTD

  公开号：WO2006029089A3

  公开（公告）日：2007-05-24
• An optically active terpenic synthon for .DELTA.9-cannabinoids: synthesis of (-)-11-hydroxy-.DELTA.9-tetrahydrocannabinol (THC) and its 1',1'-dimethylheptyl analog
  作者：Craig Siegel、Patrick M. Gordon、Raj K. Razdan

  DOI：10.1021/jo00284a011

  日期：1989.11
• SIEGEL, CRAIG;GORDON, PATRICK M.;RAZDAN, RAJ K., J. ORG. CHEM., 54,(1989) N3, C. 5428-5430
  作者：SIEGEL, CRAIG、GORDON, PATRICK M.、RAZDAN, RAJ K.

  DOI：——

  日期：——