(1aα,2β,7bα)-2-Methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropanapthalene | 132316-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1aα,2β,7bα)-2-Methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropanapthalene
• 英文别名: (1aα,2β,7bα)-2-Methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]napthalene；Xarqtymmwzajiv-ijlutslnsa-；(1aR,2R,7bS)-2-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene
• CAS: 132316-85-9
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: XARQTYMMWZAJIV-IJLUTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

上下游信息

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 、 乙醇 、 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 25.0h， 生成 (1aα,2β,7bα)-2-Methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropanapthalene
  参考文献：
  名称：

  Proton-carbon-13 coupling constants in carbocations. 6. Generation and trapping of the (1a.alpha.,7a.alpha.)-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-2-yl cation

  摘要：

  New synthetic routes to (1a-alpha,2-beta,7b-alpha)-1a,2,3,7b-tetrahydro-1H-cyclopropa[alpha]naphthalen-2-ol (4b) and (1a-alpha,2-alpha,7a-alpha)-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-2-ol (6b) have been established involving dichlorocarbene addition to the appropriate dihydronaphthalene as the key step. Ionization of either alcohol 4b or 6b in FSO3H/SO2CIF at - 130-degrees-C produces the title cation 5b, in which the positive charge is stabilized by the adjacent benzo and cyclopropyl moieties. This is the same cation as that obtained previously by protonation of 1,6-methanol[10]annulene (1). Generation of the cation 5b by protonation of C11-C-13-enriched 1 has shown that the C11 bridge methylene carbon is incorporated into both benzylic positions (C2 and C7) and not the apical cyclopropyl carbon (C1). Application of the DELTA-J equation shows that 5b adopts an anti-boat conformation in this superacid medium.

  DOI：

  10.1021/jo00006a015

文献信息

• Proton-carbon-13 coupling constants in carbocations. 6. Generation and trapping of the (1a.alpha.,7a.alpha.)-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-2-yl cation
  作者：David P. Kelly、Martin G. Banwell、Neil K. Ireland、Allison L. Noel

  DOI：10.1021/jo00006a015

  日期：1991.3

  New synthetic routes to (1a-alpha,2-beta,7b-alpha)-1a,2,3,7b-tetrahydro-1H-cyclopropa[alpha]naphthalen-2-ol (4b) and (1a-alpha,2-alpha,7a-alpha)-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-2-ol (6b) have been established involving dichlorocarbene addition to the appropriate dihydronaphthalene as the key step. Ionization of either alcohol 4b or 6b in FSO3H/SO2CIF at - 130-degrees-C produces the title cation 5b, in which the positive charge is stabilized by the adjacent benzo and cyclopropyl moieties. This is the same cation as that obtained previously by protonation of 1,6-methanol[10]annulene (1). Generation of the cation 5b by protonation of C11-C-13-enriched 1 has shown that the C11 bridge methylene carbon is incorporated into both benzylic positions (C2 and C7) and not the apical cyclopropyl carbon (C1). Application of the DELTA-J equation shows that 5b adopts an anti-boat conformation in this superacid medium.