(+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol | 80113-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol
• 英文别名: 1-(1,3-Dithian-2-yl)-4-(2-hydroxypropan-2-yl)cyclohex-2-en-1-ol
• CAS: 80113-04-8
• 化学式: C₁₃H₂₂O₂S₂
• 分子量: 274.448
• InChiKey: VELAUOHROYKNMB-UHFFFAOYSA-N

物化性质

• 沸点：
  433.6±45.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol 在 咪唑 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.0h， 生成 (+/-)-3-Norpentyl-3-(1',1'-dimethylheptyl)-9-normethyl-9-(1,3-dithianyl)-Δ9-tetrahydrocannabiol tert-butyldimethylsilyl ether
  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
• 作为产物：
  描述：

  2-(2-methoxy-4-trimethylsilyloxycyclohex-3-en-1-yl)propan-2-ol 在 正丁基锂 、 三氯乙酸 作用下， 以 四氯化碳 为溶剂， 反应 7.0h， 生成 (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol
  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

• 3'-Hydroxy- and (.+-.)-3',11-dihydroxy-.DELTA.9-tetrahydrocannabinol: (THC) biologically active metabolites of .DELTA.9-tetrahydrocannabinol
  作者：G. R. Handrick、R. P. Duffley、G. Lambert、J. G. Murphy、H. C. Dalzell、J. F. Howes、R. K. Razdan、B. R. Martin、L. S. Harris、W. L. Dewey

  DOI：10.1021/jm00354a011

  日期：1982.12

  metabolites of delta 9-THC, is described. Condensation of the monoterpene (+/-)-cis-p-menth-2-ene-1,8-diol (1) and (+/-)-3'-acetoxyolivetol (2) in the presence of fused ZnCl2 in CH2Cl2 gave a mixture from which the delta 9-THC derivative 3, containing small amounts of the delta 8-isomer 4, was isolated after column chromatography. This mixture was separated as their diacetates 5 and 6 by high-pressure liquid

  描述了3′-羟基-（7）和（+/-）-3′，11-二羟基-δ9-四氢大麻酚（11）（δ9-THC的代谢物）的合成。在CH2Cl2中存在稠合ZnCl2的情况下单萜（+/-）-顺-对-薄荷基-2-烯-1,8-二醇（1）和（+/-）-3'-乙酰氧基油醇（2）的缩合得到的混合物经柱色谱分离，分离出含有少量δ8-异构体4的δ9 -THC衍生物3。通过高压液相色谱将该混合物分离为其二乙酸酯5和6。5的碱性水解（在MeOH中的5％KOH）的水解提供了代谢物7。（+/-）-8在对甲苯磺酸的存在下与2的缩合得到9a，将其乙酰化为9b。在湿的THF中用HgO / BF3 X Et2O处理，得到醛10。用LiAlH4还原得到代谢物11。将这些代谢物与Δ9-THC进行比较，分析其抑制小鼠自发活动和直肠温度的能力以及对狗的明显行为的影响。3'-Hydroxy-delta 9-THC也已在小鼠症状学测试和犬心血管系统中与delta