1,2,3,4-tetrahydro-1,4-methanonaphthalene-9-anti-ol | 1198-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-1,4-methanonaphthalene-9-anti-ol
• 英文别名: anti-benzonorbornen-9-ol；anti-7-Hydroxy-benzobicyclo<2.2.1>hepten；syn-7-Hydroxy-benzobicyclo<2.2.1>hepten；anti-7-Hydroxy-benzonorbornen-(5)；Benzonorbornen-9-yl-anti-ol；Benznorbornen-ol-(7-anti)
• CAS: 1198-20-5
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: HEKIGGFOVMNILV-JGPRNRPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-1,4-methanonaphthalene-9-anti-ol 生成 1,2,3,4-tetrahydro-1,4-methanonaphthalen-9-one
  参考文献：
  名称：

  POLAROGRAPHY OF 7-BENZONORBORNENONES

  摘要：

  不可用。

  DOI：

  10.1139/v66-016
• 作为产物：
  描述：

  1,2,3,4-tetrahydro-1,4-methanonaphthalen-9-one 生成 1,2,3,4-tetrahydro-1,4-methanonaphthalene-9-anti-ol
  参考文献：
  名称：

  Application of photoelectron spectroscopy to intramolecular hydrogen bonding. 6. The relative importance of electrostatic and covalent contributions to the hydrogen bond of hydrogen-bonded alcohols containing a conjugated olefin as the electron donor

  摘要：

  DOI：

  10.1021/ja00462a006

文献信息

• Electronic Control of Stereoselectivity in the Metal Hydride Reductions of 1,2,3,4-Tetrahydro-1,4-methanonaphthalen-9-ones
  作者：Keiji Okada、Seiji Tomita、Masaji Oda

  DOI：10.1246/bcsj.62.459

  日期：1989.2

  Stereoselectivity in the metal hydride reduction of a series of substituted 1,2,3,4-tetrahydro-1,4-methanonaphthalen-9-ones was investigated in relation to their homoconjugation character. The observed stereoselectivity sequence was found to be parallel with the homoconjugation sequence: the portion of anti-attack increases as the benzene ring becomes electron-rich. The results are rationalized in

  研究了一系列取代的 1,2,3,4-四氢-1,4-methanonaphthalen-9-ones 的金属氢化物还原的立体选择性与其同共轭特征。发现观察到的立体选择性序列与同共轭序列平行：随着苯环变得富电子，抗攻击部分增加。结果根据 Cieplak 提出的过渡态模型或过渡态中非经典碳正离子的贡献进行了合理化。
• X-ray Crystal Structures of a Benzonorbornenyl Cation and of a Protonated Benzonorbornenol
  作者：Thomas Laube

  DOI：10.1021/ja040115t

  日期：2004.9.1

  water molecule is expected to give the parent cation H-1+. The hydrogen atoms on the oxonium O atom are involved in strong hydrogen bonds to chlorosulfonate anions and probably partially disordered despite the large estimated pK(a) differences between the corresponding acid-base pairs. The experimentally determined cation structures are compared with structures computed by DFT methods. Detailed experimental

  9-甲基苯并降冰片烯基阳离子 Me-1+ 的晶体结构显示 sp(2)-杂化碳原子 C9 与芳环（C4a-C9 与 C8a-C9 = 1.897(10) A 相同）之间的相互作用较强。阴离子 Sb(2)F(11)(-) 被细化为沿 Sb...Sb 轴旋转无序。与 Me-1+ 的发现形成鲜明对比的是，质子化的抗苯并降冰片烯醇 5+ 本质上是一种氧鎓离子，尽管它已经是一个带正电荷的离子，但在 C9 桥和芳环之间只有微弱的相互作用。预计失去一个水分子会产生母体阳离子 H-1+。尽管相应的酸碱对之间的估计 pK(a) 差异很大，但氧鎓 O 原子上的氢原子与氯磺酸根阴离子形成强氢键，并且可能部分无序。将实验确定的阳离子结构与通过 DFT 方法计算的结构进行比较。给出了详细的实验步骤。
• Bridged aromatic alkenes for the study of carbocation–π interaction
  作者：Thomas A. Spencer、Janeta Popovici-Müller、Bobbijo van Beusichem、Celeste Viscardi MacMillan、Carolee F. Lavey、Jessica M. Sin、Robert Ditchfield

  DOI：10.1016/j.tet.2010.04.029

  日期：2010.6

  Toward the goal of gaining further insight into carbocation-pi interactions, bridged-ring aromatic alkene model systems are being investigated in which one isomer will permit pi complexation of an intramolecular tertiary carbocation with a benzene ring, but the other isomer will not. The syntheses of three sets of such isomers, having, respectively, benzobicyclo[3.21]octene, benzobicyclo[2.2.1]heptene, and benzobicyclo[4.2.1]nonene structures, are described. (C) 2010 Elsevier Ltd. All rights reserved.
• Benzonorbornene and derivatives. III. Solvolysis of syn- and anti-7-bromobenzonorbornadiene and related bromides
  作者：James W. Wilt、Philip J. Chenier

  DOI：10.1021/jo00830a066

  日期：1970.5
• Substituent Effects and Homobenzylic Conjugation in <i>anti</i>-7-Benzonorbornenyl <i>p</i>-Bromobenzenesulfonate Solvolyses^1-4
  作者：Hiroshi. Tanida、Teruji. Tsuji、Hiroyuki. Ishitobi

  DOI：10.1021/ja01076a034

  日期：1964.11