Acetic acid (6aR,9S,10aR)-9-acetoxymethyl-6,6-dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-yl ester | 74128-67-9

• 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: Acetic acid (6aR,9S,10aR)-9-acetoxymethyl-6,6-dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-yl ester
• CAS: 74128-67-9；74128-68-0
• 化学式: C₂₅H₃₆O₅
• 分子量: 416.558
• InChiKey: YKGBTFFKORCXHI-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  7α-oxohexahydrocannabinol acetate 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 Acetic acid (6aR,9S,10aR)-9-acetoxymethyl-6,6-dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-yl ester
  参考文献：
  名称：

  Activity of novel aminocannabinoids in baboons

  摘要：

  The axial and equatorial isomers of 7-(methylamino)hexahydrocannabinol (1 and 2) and 7-(dimethylamino)hexahydrocannabinol (3 and 4) were prepared by reductive amination of the corresponding cannabinoid aldehydes. The amines caused some tranquility in baboons but did not evoke the typical cannabimimetic syndrome caused by psychoactive cannabinoids. However the axial amines (1 and 3) but not the equatorial ones (2 and 4) caused bouts of scratching and yawning. The latter is a rare pharmacological effect hitherto not observed with other cannabinoids.

  DOI：

  10.1021/jm00376a029

文献信息

• Stereochemical requirements for cannabinoid activity
  作者：R. Mechoulam、N. Lander、T. H. Varkony、I. Kimmel、O. Becker、Z. Ben-Zvi、H. Edery、G. Porath

  DOI：10.1021/jm00184a002

  日期：1980.10

  Several pairs of cannabinoid isomers were synthesized and tested for psychotropic activity in rhesus monkeys. Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity. (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent psychotropic activity.