1-oxymethylenemethoxy-3-methoxy-5-pentylbenzene | 80393-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-oxymethylenemethoxy-3-methoxy-5-pentylbenzene
• 英文别名: 1-Methoxy-3-(methoxymethoxy)-5-pentylbenzene
• CAS: 80393-04-0
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: MDQDACMJEFJXOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxymethylenemethoxy-3-methoxy-5-pentylbenzene 在 乙醇 、 三甲基溴硅烷 、 4 A molecular sieve 、 氨 、 lithium 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 1-丙烷硫醇钠 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.08h， 生成 Trifluoro-methanesulfonic acid (6aR,10aR)-1-methoxymethoxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-9-yl ester
  参考文献：
  名称：

  Synthesis of (.+-.)-11-nor-9-carboxy-.DELTA.9-tetrahydrocannabinol. New synthetic approaches to cannabinoids

  摘要：

  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.

  DOI：

  10.1021/jo00004a027
• 作为产物：
  描述：

  3-methoxy-5-pentylphenol 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到1-oxymethylenemethoxy-3-methoxy-5-pentylbenzene
  参考文献：
  名称：

  Synthesis of (.+-.)-11-nor-9-carboxy-.DELTA.9-tetrahydrocannabinol. New synthetic approaches to cannabinoids

  摘要：

  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.

  DOI：

  10.1021/jo00004a027

文献信息

• de la Torre, M.; Garcia, F.; Cruz, R, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1251 - 1252
  作者：de la Torre, M.、Garcia, F.、Cruz, R

  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：——
• 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.