(+/-)-nor-Δ(9)-cis-6a,10a-tetrahydrocannabinol-9-carboxylic acid | 122797-75-5

• 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: (+/-)-nor-Δ(9)-cis-6a,10a-tetrahydrocannabinol-9-carboxylic acid
• 英文别名: (6aS,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid
• CAS: 122797-75-5
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: YOVRGSHRZRJTLZ-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2,6-dimethoxy-4-pentylphenyl)lithium 在 palladium diacetate 、 甲酸 、 jones reagent 、 氨 、 4-甲基苯磺酸吡啶 、 三溴化硼 、 lithium 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 丁酮 为溶剂， 反应 84.58h， 生成 (+/-)-nor-Δ(9)-cis-6a,10a-tetrahydrocannabinol-9-carboxylic acid
  参考文献：
  名称：

  Regioselective synthesis of (.+-.)-11-Nor-9-carboxy-.DELTA.9-THC

  摘要：

  DOI：

  10.1021/jo00281a009

文献信息

• Synthesis of (±)-nor-Δ⁹-cis-6a,10a-THC-9-carboxylic acid (THC = tetrahydrocannabinol)
  作者：Marcus A. Tius、Xue-qin Gu

  DOI：10.1039/c39890001171

  日期：——

  A convenient synthesis of the recemate of the cis-6a,10a-isomer of the major human urinary metabolite of Δ9-tetrahydrocannabinol has been accomplished.

  人类尿液中δ9-四氢大麻酚的主要代谢物顺式-6a,10a-异构体的受体的简便合成已经完成。
• Synthesis of (.+-.)-11-nor-9-carboxy-.DELTA.9-tetrahydrocannabinol. New synthetic approaches to cannabinoids
  作者：John W. Huffman、Xuehai Zhang、Ming Jung Wu、H. Howard Joyner、William T. Pennington

  DOI：10.1021/jo00004a027

  日期：1991.2

  A completely regioselective synthesis of (+/-)-11-nor-9-carboxy-DELTA-9-tetrahydrocannabinol (1), a principal human metabolite of DELTA-9-tetrahydrocannabinol (2), has been carried out in seven steps and 14% overall yield from apoverbenone (9) and the bis-MOM ether of olivetol. Condensation of 9 with the aryllithium derived from the bis-MOM ether of olivetol gives an unstable tertiary allylic alcohol that undergoes oxidative rearrangement to give enone 42. Reaction of 42 with acid results in hydrolysis of the MOM ethers and cyclization to benzopyranone 21. Conversion to MOM ether 39 followed by Li/NH3 reduction and trapping of the enolate with N-phenyltriflimide gives vinyl triflate 40 plus the isomer with a cis ring fusion. Palladium-catalyzed carboxylation, hydrolysis of the MOM ether, and separation from cis acid 41 gives pure 1. Model experiments employing unsubstituted resorcinol derivatives that lead to ester 27 are described, as are a number of alternative approaches to acid 1.
• HUFFMAN, JOHN W.;ZHANG, XUEHAI;WU, MING-JUNG;JOYNER, HOWARD H., J. ORG. CHEM., 54,(1989) N0, C. 4741-4743
  作者：HUFFMAN, JOHN W.、ZHANG, XUEHAI、WU, MING-JUNG、JOYNER, HOWARD H.

  DOI：——

  日期：——
• TIUS, MARCUS A.;GU, XUE-QIN, J. CHEM. SOC. CHEM. COMMUN.,(1989) N6, C. 1171-1173
  作者：TIUS, MARCUS A.、GU, XUE-QIN

  DOI：——

  日期：——
• HUFFMAN, JOHN W.;ZHANG, XUEHAI;WU, MING-JUNG;JOYNER, H. HOWARD;PENNINGTON+, J. ORG. CHEM., 56,(1991) N, C. 1481-1489
  作者：HUFFMAN, JOHN W.、ZHANG, XUEHAI、WU, MING-JUNG、JOYNER, H. HOWARD、PENNINGTON+

  DOI：——

  日期：——