(6aR,10aR)-3-(5-tert-butyldimethylsilyloxypentyl)-6a,7,10,10-tetrahydro-1-tert-butyldimethylsilyloxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9(8H)-one | 197178-50-0

• 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: (6aR,10aR)-3-(5-tert-butyldimethylsilyloxypentyl)-6a,7,10,10-tetrahydro-1-tert-butyldimethylsilyloxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9(8H)-one
• CAS: 197178-50-0
• 化学式: C₃₂H₅₆O₄Si₂
• 分子量: 560.965
• InChiKey: XDYRUVUJWFVXDZ-CLJLJLNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.43
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (6aR,10aR)-3-(5-tert-butyldimethylsilyloxypentyl)-6a,7,10,10-tetrahydro-1-tert-butyldimethylsilyloxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9(8H)-one 在 palladium diacetate 2,6-二叔丁基-4-甲基吡啶 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 (6aR,10aR)-3-(5-hydroxypentyl)-9-methoxycarbonyl-6a,7,10,10-tetrahydro-1-tert-butyldimethylsilyloxy-6,6-dimethyl-6H-dibenzo[b,d]pyran
  参考文献：
  名称：

  Synthesis of 5′,11-dihydroxy-Δ8-tetrahydrocannabinol

  摘要：

  The synthesis of a polar cannabinoid, 5',11-dihydroxy-Delta(8)-tetrahydrocannabinol (2), has been carried out. A key step in the synthesis is the reaction of an aryllithium derived from 1-(tert-butyldimethylsilyloxy)-5-(3, 5-dimethoxyphenyl)pentane with apoverbenone. Subsequent conversions provided diol 2, which has significantly less affinity for the cannabinoid receptor than Delta(8)-THC. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00868-5
• 作为产物：
  描述：

  5-(3,5-二甲氧基苯基)戊酸乙酯 在 咪唑 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 正丁基锂 、 三氯化铝 、 丙烷-1-硫醇 、 氨 、 lithium 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 124.0h， 生成 (6aR,10aR)-3-(5-tert-butyldimethylsilyloxypentyl)-6a,7,10,10-tetrahydro-1-tert-butyldimethylsilyloxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9(8H)-one
  参考文献：
  名称：

  Synthesis of 5′,11-dihydroxy-Δ8-tetrahydrocannabinol

  摘要：

  The synthesis of a polar cannabinoid, 5',11-dihydroxy-Delta(8)-tetrahydrocannabinol (2), has been carried out. A key step in the synthesis is the reaction of an aryllithium derived from 1-(tert-butyldimethylsilyloxy)-5-(3, 5-dimethoxyphenyl)pentane with apoverbenone. Subsequent conversions provided diol 2, which has significantly less affinity for the cannabinoid receptor than Delta(8)-THC. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00868-5

文献信息

• Synthesis of 5′,11-dihydroxy-Δ8-tetrahydrocannabinol
  作者：John W. Huffman、Ming-Jung Wu、W.Kenneth Banner、Dong Dai

  DOI：10.1016/s0040-4020(97)00868-5

  日期：1997.9

  The synthesis of a polar cannabinoid, 5',11-dihydroxy-Delta(8)-tetrahydrocannabinol (2), has been carried out. A key step in the synthesis is the reaction of an aryllithium derived from 1-(tert-butyldimethylsilyloxy)-5-(3, 5-dimethoxyphenyl)pentane with apoverbenone. Subsequent conversions provided diol 2, which has significantly less affinity for the cannabinoid receptor than Delta(8)-THC. (C) 1997 Elsevier Science Ltd.