11-oxo-6a,10a-trans-Δ⁹-THC | 52663-85-1

• 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: 11-oxo-6a,10a-trans-Δ⁹-THC
• 英文别名: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carbaldehyde
• CAS: 52663-85-1；67145-57-7
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: HQRKNUDGMPVIMO-IAGOWNOFSA-N

物化性质

• 沸点：
  431.1±45.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-oxo-6a,10a-trans-Δ⁹-THC 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以99%的产率得到6a,7,8,10a-四氢-1-羟基-6,6-二甲基-3-戊基-6H-二苯并(b,d)吡喃-9-甲醇
  参考文献：
  名称：

  The synthesis of some 11-substituted tetrahydrocannabinol metabolites

  摘要：

  9-溴-11-酮-大麻酚（5）是通过经过环氧磺酮4处理的酮大麻酚3b制备的。 溴醛5的脱溴反应可以控制，从而得到热力学上更稳定的Δ8-醛2c，或者通过分子内辅助消除得到Δ9-醛1c。 对不饱和醛的还原分别产生了烯丙醇代谢物2a和1a。

  DOI：

  10.1139/v82-403
• 作为产物：
  描述：

  2-(2-methoxy-4-trimethylsilyloxycyclohex-3-en-1-yl)propan-2-ol 在 正丁基锂 、 三氟化硼乙醚 、 对甲苯磺酸 、 mercury(II) oxide 、 三氯乙酸 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 8.25h， 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

文献信息

• 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。
• 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：——
• The synthesis of some 11-substituted tetrahydrocannabinol metabolites
  作者：John W. ApSimon、T. Lee Collier、Michael D. Guiver

  DOI：10.1139/v82-403

  日期：1982.11.15

  9-Bromo-11-oxo-hexahydrocannabinol (5) was prepared from the ketocannabinoid 3b via the epoxysulfone 4. The dehydrobromination of the bromoaldehyde 5 could be controlled to give either the thermodynamically more stable Δ⁸-aldehyde 2c, or the Δ⁹-aldehyde 1c by an intramolecularly assisted elimination. Reduction of the unsaturated aldehydes gave the allylic alcohol metabolites 2a and 1a, respectively.

  9-溴-11-酮-大麻酚（5）是通过经过环氧磺酮4处理的酮大麻酚3b制备的。 溴醛5的脱溴反应可以控制，从而得到热力学上更稳定的Δ8-醛2c，或者通过分子内辅助消除得到Δ9-醛1c。 对不饱和醛的还原分别产生了烯丙醇代谢物2a和1a。
• 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).