9-THC> | 131323-43-8

• 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: 9-THC>
• 英文别名: (8R,16S)-5,9,9-trimethyl-13-pentyl-2,10-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,11,13-tetraene
• CAS: 131323-43-8
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: FKTYERLCRZROFJ-YLJYHZDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  四氢大麻酚 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 对甲苯磺酸 、 N,N-二甲基苯胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.45h， 生成 9-THC>
  参考文献：
  名称：

  Synthesis of rotationally restricted tetrahydrocannabinol ethers

  摘要：

  Two rotationally restricted tetrahydrocannabinol (THC) ethers were synthesized to test the concept that the psychopharmacological activity of cannabinoids derives, in part, from the orientation of the lone pairs of electrons of the phenolic hydroxyl oxygen. These compounds, O,2-propano-DELTA-8-THC (3) and O,10-methano-DELTA-9-THC (12), lock the orientation of the lone pairs of electrons toward and away from the cyclohexene ring, respectively, by restricting bond rotation through the formation of cyclic ethers. The synthesis of 3 was achieved by alkylation of the phenolic oxygen of DELTA-8-THC (1) with 3-bromo-1-propanol followed by cyclodehydration in the presence of phosphorus pentoxide. The synthesis of 12 was achieved from a sequence of reactions that involved the cyclization of a chloroformate in a modification of the Darzens acylation of olefins. Thus, treatment of DELTA-9-THC with phosgene in the presence of N,N-dimethylaniline afforded DELTA-9-THC chloroformate. Subsequent intramolecular cycloaddition of the chloroformyl moiety to the DELTA-9-unsaturation in the presence of AlCl3 afforded the corresponding beta-chloro ester 9. Treatment of 9 with lithium aluminum hydride gave 10-(hydroxymethyl)-DELTA-9-THC (10). Compound 12 and 10-methylene-DELTA-8-THC (11) were obtained as a readily separable mixture by treatment of 10 with 3 mol of tosyl chloride in pyridine. C-13 NMR and H-1 NMR spectral assignments were made. A model study of the TiCl4-mediated cleavage of the MEM ether of phenol demonstrated generation of the phenoxymethyl cation.

  DOI：

  10.1021/jo00004a039

文献信息

• Synthesis of rotationally restricted tetrahydrocannabinol ethers
  作者：Herbert H. Seltzman、Yung Ao Hsieh、Colin G. Pitt、Patricia H. Reggio

  DOI：10.1021/jo00004a039

  日期：1991.2

  Two rotationally restricted tetrahydrocannabinol (THC) ethers were synthesized to test the concept that the psychopharmacological activity of cannabinoids derives, in part, from the orientation of the lone pairs of electrons of the phenolic hydroxyl oxygen. These compounds, O,2-propano-DELTA-8-THC (3) and O,10-methano-DELTA-9-THC (12), lock the orientation of the lone pairs of electrons toward and away from the cyclohexene ring, respectively, by restricting bond rotation through the formation of cyclic ethers. The synthesis of 3 was achieved by alkylation of the phenolic oxygen of DELTA-8-THC (1) with 3-bromo-1-propanol followed by cyclodehydration in the presence of phosphorus pentoxide. The synthesis of 12 was achieved from a sequence of reactions that involved the cyclization of a chloroformate in a modification of the Darzens acylation of olefins. Thus, treatment of DELTA-9-THC with phosgene in the presence of N,N-dimethylaniline afforded DELTA-9-THC chloroformate. Subsequent intramolecular cycloaddition of the chloroformyl moiety to the DELTA-9-unsaturation in the presence of AlCl3 afforded the corresponding beta-chloro ester 9. Treatment of 9 with lithium aluminum hydride gave 10-(hydroxymethyl)-DELTA-9-THC (10). Compound 12 and 10-methylene-DELTA-8-THC (11) were obtained as a readily separable mixture by treatment of 10 with 3 mol of tosyl chloride in pyridine. C-13 NMR and H-1 NMR spectral assignments were made. A model study of the TiCl4-mediated cleavage of the MEM ether of phenol demonstrated generation of the phenoxymethyl cation.