(-)-(6aR,10aR)-9-carboxy-3-(1',1'-dimethylheptyl)-6a,7,8,10a-tetrahydro-6,6-dimethyl-6H-dibenzopyran-1-ol | 138176-21-3

• 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-carboxy-3-(1',1'-dimethylheptyl)-6a,7,8,10a-tetrahydro-6,6-dimethyl-6H-dibenzopyran-1-ol
• 英文别名: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid；THC, 9-Nor-9-carboxy-delta 8；(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid
• CAS: 138176-21-3
• 化学式: C₂₅H₃₆O₄
• 分子量: 400.558
• InChiKey: SMDPUJSGXVIWSO-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carbaldehyde 在 咪唑 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 (-)-(6aR,10aR)-9-carboxy-3-(1',1'-dimethylheptyl)-6a,7,8,10a-tetrahydro-6,6-dimethyl-6H-dibenzopyran-1-ol
  参考文献：
  名称：

  Studies on the Synthesis of (-)-11-Nor-9-carboxy-Δ⁹-Tetrahydrocannabinol (THC) and Related Compounds: An Improved Oxidative Procedure

  摘要：

  本文介绍了一种简便的方法，即在大量过量的 2-甲基-2-丁烯存在下，用亚氯酸钠将δ9-四氢大麻酚醛 4 及其叔丁基二甲基硅烷衍生物方便地氧化成相应的酸，而不会发生δ9-双键的异构化。 在四氢呋喃中用四丁基氟化铵对 O 保护基进行脱保护处理，得到酸 2，总收率≥80%。对其他氧化剂和保护基团的研究表明，这是制备 9-羧基-δ9-四氢大麻酚的首选方法。

  DOI：

  10.1055/s-1991-26590

文献信息

• Synthesis of racemic and optically active .DELTA.9-tetrahydrocannabinol (THC) metabolites
  作者：Craig Siegel、Patrick M. Gordon、David B. Uliss、G. Richard Handrick、Haldean C. Dalzell、Raj. K. Razdan

  DOI：10.1021/jo00024a031

  日期：1991.11

  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).
• CANNABINOIDS AND USES THEREOF
  申请人：Corbus Pharmaceuticals, Inc.

  公开号：US20210284621A1

  公开（公告）日：2021-09-16

  The invention relates to cannabinoid compounds, pharmaceutical compositions including one or more cannabinoid compounds, and the use of pharmaceutical compositions including one or more cannabinoid compounds for the treatment of a disease or condition (e.g., a fibrotic disease or an inflammatory disease) in a subject in need thereof.
• Studies on the Synthesis of (-)-11-Nor-9-carboxy-Δ⁹-Tetrahydrocannabinol (THC) and Related Compounds: An Improved Oxidative Procedure
  作者：Craig Siegel、Patrick M. Gordon、Raj K. Razdan

  DOI：10.1055/s-1991-26590

  日期：——

  A facile procedure is described whereby Δ9-THC aldehydes 4, as their tert-butyldimethylsilyl derivatives, are conveniently oxidized to the corresponding acids with sodium chlorite in the presence of a large excess of 2-methyl-2-butene without isomerization of the Δ9-double bond. Deprotection of the O-protecting group with tetrabutylammonium fluoride in tetrahydrofuran gave the acids 2 in an overall yield of ≥ 80%. A study of other oxidizing agents and protecting groups demonstrated that this is the procedure of choice for the preparation of 9-carboxy-Δ9-tetrahydrocannabinols.

  本文介绍了一种简便的方法，即在大量过量的 2-甲基-2-丁烯存在下，用亚氯酸钠将δ9-四氢大麻酚醛 4 及其叔丁基二甲基硅烷衍生物方便地氧化成相应的酸，而不会发生δ9-双键的异构化。 在四氢呋喃中用四丁基氟化铵对 O 保护基进行脱保护处理，得到酸 2，总收率≥80%。对其他氧化剂和保护基团的研究表明，这是制备 9-羧基-δ9-四氢大麻酚的首选方法。