7-phenylnorbornane | 24892-78-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 7-phenylnorbornane
• 英文别名: 7-Phenylnorbornan；7-Phenylbicyclo[2.2.1]heptane
• CAS: 24892-78-2
• 化学式: C₁₃H₁₆
• 分子量: 172.27
• InChiKey: VCNXHLSPJCDICN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  7-phenylnorbornane 在 triphenylmethyl perchlorate 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 74.5h， 生成 spiro[8aH-azulene-3,7'-bicyclo[2.2.1]heptane]-1,1,2,2-tetracarbonitrile
  参考文献：
  名称：

  Stereomutation of 7-tropylionorbornane, 2-tropyliobicyclo[2.2.2]octane, and 2-tropylioadamantane: evidence for the intermediacy of heptafulvenes

  摘要：

  The perchlorates of 7-tropylionorbornane (3), 2-tropyliobicyclo[2.2.2]octane (4), and 2-tropylioadamantane (5) were found to undergo stereomutation in acetonitrile at 25-85-degrees-C, as evidenced by following the change in the C-13 NMR spectra of their deuterium-labeled compounds in acetonitrile-d3. Addition of tetracyanoethylene to their solutions in acetonitrile gave the [8 + 2] cycloaddition products of the corresponding heptafulvenes, indicating the intermediacy of the heptafulvenes. This stereomutation was too slow to detect in dichloromethane at the same temperature. Therefore, it is concluded that the stereomutation proceeds through the abstraction of the alpha-hydrogen by acetonitrile as a base followed by the protonation of the heptafulvene intermediate from the rear side. The entropies of activation which are significantly negative and large indicate abstraction of the alpha-hydrogen is the rate-determining step. The enthalpy of activation for the norbornane system (22.1 +/- 1.1 kcal/mol) is about 8 kcal/mol greater than that for the bicyclo[2.2.2]octane system (15.4 +/- 1.1 kcal/mol) and that for the adamantane system (13.1 +/- 1.3 kcal/mol). Molecular mechanics calculations (MMPI, MM2') for the three heptafulvenes and the corresponding phenyl derivatives (instead of the tropylium ions) indicated that the angle strain at the 8-position of the heptafulvenes controls the rate of the steremutation.

  DOI：

  10.1021/jo00003a028
• 作为产物：
  描述：

  7-phenyl-7-methoxynorbornane 在 potassium alloy 、 sodium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 7-phenylnorbornane
  参考文献：
  名称：

  Structure of the 7-phenylnorbornyl carbanion. A pyramidal organolithium and planar organopotassium

  摘要：

  DOI：

  10.1021/ja00534a025

文献信息

• King, James Frederick; Lee, Teresa Mee-Ling, Canadian Journal of Chemistry, 1981, vol. 59, p. 362 - 372
  作者：King, James Frederick、Lee, Teresa Mee-Ling

  DOI：——

  日期：——
• Aromatic substitution. 64. Friedel-Crafts Alkylation of Aromatics with exo-2-Chloro- and 7-Chloronorbornane
  作者：George A. Olah、Chang Soo Lee、G. K. Surya Prakash

  DOI：10.1021/jo00088a049

  日期：1994.5

  exo-2-Chloro- and 7-chloronorbornane in the presence of tin(IV) chloride or aluminum chloride react with benzene and substituted benzenes to give the corresponding norbornylated products. Mechanistic aspects of the reactions proceeding through carbocationic intermediates are discussed.
• IKAI, KEIZO;TAKEUCHI, KENICHI;KINOSHITA, TOMOMI;HAGA, KENICHI;KOMATSU, KO+, J. ORG. CHEM., 56,(1991) N, C. 1052-1058
  作者：IKAI, KEIZO、TAKEUCHI, KENICHI、KINOSHITA, TOMOMI、HAGA, KENICHI、KOMATSU, KO+

  DOI：——

  日期：——
• KING J. F.; LEE TERESA MEE-LING, CAN. J. CHEM., 1981, 59, NO 2, 362-372
  作者：KING J. F.、 LEE TERESA MEE-LING

  DOI：——

  日期：——
• Stereomutation of 7-tropylionorbornane, 2-tropyliobicyclo[2.2.2]octane, and 2-tropylioadamantane: evidence for the intermediacy of heptafulvenes
  作者：Keizo Ikai、Kenichi Takeuchi、Tomomi Kinoshita、Kenichi Haga、Koichi Komatsu、Kunio Okamoto

  DOI：10.1021/jo00003a028

  日期：1991.2

  The perchlorates of 7-tropylionorbornane (3), 2-tropyliobicyclo[2.2.2]octane (4), and 2-tropylioadamantane (5) were found to undergo stereomutation in acetonitrile at 25-85-degrees-C, as evidenced by following the change in the C-13 NMR spectra of their deuterium-labeled compounds in acetonitrile-d3. Addition of tetracyanoethylene to their solutions in acetonitrile gave the [8 + 2] cycloaddition products of the corresponding heptafulvenes, indicating the intermediacy of the heptafulvenes. This stereomutation was too slow to detect in dichloromethane at the same temperature. Therefore, it is concluded that the stereomutation proceeds through the abstraction of the alpha-hydrogen by acetonitrile as a base followed by the protonation of the heptafulvene intermediate from the rear side. The entropies of activation which are significantly negative and large indicate abstraction of the alpha-hydrogen is the rate-determining step. The enthalpy of activation for the norbornane system (22.1 +/- 1.1 kcal/mol) is about 8 kcal/mol greater than that for the bicyclo[2.2.2]octane system (15.4 +/- 1.1 kcal/mol) and that for the adamantane system (13.1 +/- 1.3 kcal/mol). Molecular mechanics calculations (MMPI, MM2') for the three heptafulvenes and the corresponding phenyl derivatives (instead of the tropylium ions) indicated that the angle strain at the 8-position of the heptafulvenes controls the rate of the steremutation.