(+)-Nabilone | 61664-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (+)-Nabilone
• 英文别名: (-)-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one；(6aS,10aS)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one
• CAS: 61664-39-9
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: GECBBEABIDMGGL-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (6aS,10aS)-(+)-1-Methoxy-3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-6,6-dimethyl-9H-dibenzopyran-9-one 在 丙烷-1-硫醇 、 sodium hydride 作用下， 生成 (+)-Nabilone
  参考文献：
  名称：

  Synthesis of both enantiomers of nabilone from a common intermediate. Enantiodivergent synthesis of cannabinoids

  摘要：

  Both enantiomers of the synthetic cannabinoid nabilone (4) have been synthesized from a common intermediate, enone 7. Enone 7 was prepared by reaction of [2,6-dimethoxy-4-(1,1-dimethylheptyl)phenyl]lithium with (+)-apoverbenone (2), followed by PDC oxidation. Li/NH3 reduction of 7 gave saturated ketone 9, which, after ether cleavage to 10, afforded (6aS,10aR)-hexahydrodibenzopyran 15 on reaction with SnCl4. Isomerization to 6aR,10aR ketone 16 followed by ether cleavage gave the 6aR,10aR enantiomer of nabilone (4). The 6aS,10aS enantiomer of 4 (24) was prepared from 7 by ether cleavage to 18 and rearrangement to nonracemic tetrahydrodibenzopyran 20 using AlCl3. Dissolving metal reduction of 20 followed by ether cleavage gave the 6aS,10aS enantiomer of nabilone (24). A model sequence employing (2,6-dimethoxyphenyl)lithium at the first step was carried out and the structure of one of the intermediates, ketone 12, was established by X-ray crystallography. A new preparation of apoverbenone (2) has been developed.

  DOI：

  10.1021/jo00006a021

文献信息

• Process for preparing synthetic cannabinoids
  申请人：STEUP CHRISTIAN

  公开号：US20100298579A1

  公开（公告）日：2010-11-25

  The field of the invention is organic synthesis, more particularly a process for preparing cannabinoids. The process described is applicable to all stereoisomers and homologues of cannabinoids. For this purpose, the present patent application provides a process for preparing the abovementioned compounds in two or three chemical synthesis steps.

  本发明领域是有机合成，更具体地是一种制备大麻素的过程。所述过程适用于大麻素的所有立体异构体和同系物。为此，本专利申请提供了一种在两到三个化学合成步骤中制备上述化合物的方法。
• Stereoselective preparation of hexahydro dibenzopyranones and
  申请人：Eli Lilly and Company

  公开号：US04102902A1

  公开（公告）日：1978-07-25

  An optically active 4-(4-substituted-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone is reacted with a protonic acid to provide an optical isomer of a cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibe nzo[b,d]pyran-9-one. Reaction of said norpinanone with a Lewis acid provides an optical isomer of trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-di benzo[b,d]pyran-9-one. The optically active norpinanones are prepared by reaction of a 5-substituted-resorcinol with an optically active 6,6-dimethyl-2,4-diacetoxy-2-norpinene or an optically active 6,6-dimethyl-2,2-diacetoxy-3-norpinene, which compounds are derived from optically active .beta.-pinenes.

  一种光学活性的4-(4-取代-2,6-二羟基苯基)-6,6-二甲基-2-诺皮酮与质子酸反应，生成一种顺式-1-羟基-3-取代-6,6-二甲基-6,6a,7,8,10,10a-六氢-9H-二苯并[b,d]吡喃-9-酮的光学异构体。所述诺皮酮与路易斯酸反应，提供反式-1-羟基-3-取代-6,6-二甲基-6,6a,7,8,10,10a-六氢-9H-二苯并[b,d]吡喃-9-酮的光学异构体。光学活性的诺皮酮是通过将5-取代-邻苯二酚与光学活性的6,6-二甲基-2,4-二乙酰氧基-2-诺皮烯或光学活性的6,6-二甲基-2,2-二乙酰氧基-3-诺皮烯反应制备的，这些化合物源于光学活性的β-蒎烯。
• Preparation of optically active trans-hexahydrodibenzopyranones
  申请人：Eli Lilly and Company

  公开号：US04075230A1

  公开（公告）日：1978-02-21

  Reaction of a 5-substituted resorcinol with optically active apoverbenone in the presence of aluminum chloride affords an optically active trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-di benzo[b,d]pyran-9-one.

  在铝氯化物存在下，5-取代邻苯二酚与光学活性的缺口苯酮反应，得到一种光学活性的trans-1-羟基-3-取代-6,6-二甲基-6,6a,7,8,10,10a-六氢-9H-二苯并[b,d]吡喃-9-酮。
• Amino-dibenzopyrans, their preparation, formulations containing them and their use as pharmaceuticals
  申请人：ELI LILLY AND COMPANY

  公开号：EP0003883A1

  公开（公告）日：1979-09-05

  There are described novel 1-hydroxy-3- substituted- tet- rahydro and hexahydro- dibenzo[b, d]- pyrans having an amino group or amino derivative at the 9-position, of the following formula: in which R1, R2, R' and Z are as defined herein. The compounds are useful as analgesics, anti-depressants anti-anxiety agents, hypotensive agents and as intermediates for the preparation of other compounds.

  描述了新型 1-羟基-3-取代-四-拉氢和六-氢-二苯并[b,d]-吡喃，其 9 位上具有下式的氨基或氨基衍生物： 其中 R1、R2、R'和 Z 如本文所定义。这些化合物可用作镇痛剂、抗抑郁剂、抗焦虑剂、降血压剂以及制备其他化合物的中间体。
• Use of palonosetron for treating post-operative nausea and vomiting
  申请人：Helsinn Healthcare S.A.

  公开号：EP2258367A2

  公开（公告）日：2010-12-08

  Methods are provided to treat post-operative nausea and vomiting, as well as emesis generally, with 5-HT3 receptor antagonists. In particular, the invention discloses methods for reducing post-operative nausea and vomiting and other emetic events with palonosetron.

  本发明提供了用 5-HT3 受体拮抗剂治疗术后恶心和呕吐以及一般催吐的方法。特别是，本发明公开了使用帕洛诺司琼减少术后恶心和呕吐以及其他催吐事件的方法。