THC, 11-OH-delta 8 | 123331-84-0

• 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: THC, 11-OH-delta 8
• 英文别名: (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 123331-84-0
• 化学式: C₂₅H₃₈O₃
• 分子量: 386.575
• InChiKey: UEXRUIOOOVZHFZ-WOJBJXKFSA-N

物化性质

• 沸点：
  476.458±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.030±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-(-)-1-乙酰氧基-4-(1-乙酰氧基-1-甲基乙基)-1-环己烯 在 palladium diacetate 、 lithium aluminium tetrahydride 、 正丁基锂 、 碳酸丙烯乙酯 、 三氟化硼乙醚 、 三正丁基甲氧基锡 、 对甲苯磺酸 、 1,2-双(二苯基膦)乙烷 、 mercury(II) oxide 作用下， 以 乙醚 为溶剂， 反应 9.33h， 生成 THC, 11-OH-delta 8
  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

• Antipruritics
  申请人：Yasui Kiyoshi

  公开号：US20080312292A1

  公开（公告）日：2008-12-18

  It is intended to provide antipruritics (drugs to control itching, antiitch agents and drugs to stop itching). It is found out that a compound having an agonistic activity to the cannabinoid receptor shows an antipruritics effect.

  这句话的意思是：它旨在提供止痒药（控制瘙痒的药物、抗瘙痒剂和止痒药物）。发现一种具有类脂激素受体激动活性的化合物具有止痒效果。
• 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：——
• CANNABINOID RECEPTOR TARGETED AGENT
  申请人：Bornhop Darryl J.

  公开号：US20090105128A1

  公开（公告）日：2009-04-23

  Compounds of the following formula: wherein X is H or substituted with with at least one X being substituted; and halo is fluorine, chlorine, bromine, iodine; and stereoisomers and conjugable analogs thereof.
• METHODS AND COMPOSITIONS RELATING TO ULTRAPURE 5-(1,1-DIMETHYLHEPTYL)-RESORCINOL
  申请人：Corbus Pharmaceuticals, Inc.

  公开号：US20210198223A1

  公开（公告）日：2021-07-01

  The invention provides methods and compositions relating to an ultrapure formulation of 5-(1,1-dimethylheptyl)-resorcinol (ultrapure DMHR). The invention features methods for making ultrapure DMHR, including methods that minimize the production of unwanted side products (e.g., the production of homologous alkyl-chain impurities). The invention also features methods of making cannabinoids, such as (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyl-2-octanyl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid (ajulemic acid), using ultrapure DMHR, including methods that minimize the production of unwanted side products (e.g., the production of homologous alkyl-chain impurities) in the resulting cannabinoid preparation.