exo-2-aminomethylbicyclo[2.2.1]heptane

• 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: exo-2-aminomethylbicyclo[2.2.1]heptane
• 英文别名: Bicyclo(2.2.1)heptane-2-methanamine, (1R,2R,4S)-rel-；[(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl]methanamine
• 化学式: C₈H₁₅N
• 分子量: 125.214
• InChiKey: HWMZHVLJBQTGOL-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  exo-2-aminomethylbicyclo[2.2.1]heptane 在 三乙胺 作用下， 以 氯仿 、 异丙醇 为溶剂， 生成
  参考文献：
  名称：

  摘要：

  Reactions of p-nitrophenyloxirane with amines containing fragments with bicyclic skeleton of norbornene, norbornane, epoxynorbornane (stereoisomeric exo- and endo-5-an-aminomethylbicyclo[2.2.1]hept-2-enes, N-benzyl-endo-5-aminomethylbicyclo[2.2.1]hept-2-ene, endo-5-(2-aminoethyl)bicyclo[2.2.1]hept-2-ene, stereoisomeric exo- and endo-2-aminomethylbicyclo[2.2.1]beptanes, 2-(1-aminoethyl)bicyclo[2.2.1]heptane, exo-5-aminomethyl-exo-2,3-epoxybicyclo[2.2.1]heptane) were investigated. The aminolysis of p-nitrophenyloxirane occurred regioselectively according to Krasusky rule as was proved by H-1 and C-13 NMR data. As shown by H-1 and C-13 NMR spectroscopy the oxyalkylation product obtained from N-benzyl-endo-5-aminomethylbicyclo[2.2.1]hept-2-ene was composed of two diastereomers originating from the presence of a chiral nitrogen atom in the rear part of the rigid bicyclic skeleton. New products of amino groups transformation in the molecules of hydroxyamines were obtained by reaction with p-methylbenzoyl chloride and p-nitrophenylsulfonyl chloride. Regioselectivity of the attack of electrophilic reagents on the nitrogen in the hydroxyamines was confirmed by IR and H-1 NMR spectra of the products. The data on pharmacological activity tests of N-2-hydroxyethyl(p-nitrophenyl)-5-aminomethylbicyclo[2.2.1]hept-2-ene are reported.

  DOI：

  10.1023/a:1022553832553
• 作为产物：
  描述：

  5-norbornene-2-carbonitrile 在 镍 氨 、 氢气 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、8.11 MPa 条件下， 反应 10.0h， 以78%的产率得到exo-2-aminomethylbicyclo[2.2.1]heptane
  参考文献：
  名称：

  Kas'yan; Krasnovskaya; Zlenko, Russian Journal of Organic Chemistry, 1996, vol. 32, # 8, p. 1113 - 1121

  摘要：

  DOI：

文献信息

• Kas'yan; Krishchik; Krasnovskaya, Russian Journal of Organic Chemistry, 1998, vol. 34, # 12, p. 1731 - 1735
  作者：Kas'yan、Krishchik、Krasnovskaya、Kas'yan

  DOI：——

  日期：——
• Reactivity of Cage-Like Amines toward p-Toluenesulfonyl Chloride and Diphenyl Chlorophosphate in Acetonitrile
  作者：Yu. S. Sadovskii、T. N. Solomoichenko、A. O. Kas'yan、E. A. Golodaeva、S. V. Anikanova、L. I. Kas'yan、V. A. Savelova

  DOI：10.1023/b:rujo.0000034909.58849.e9

  日期：2004.1

  The nucleophilic reactivity of amines of the norbornane, norbornene, and adamantane series toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile at 25degreesC is determined mainly by the steric factor. Parameters characterizing spatial accessibility of the reaction center in the amine molecule have been determined. Cage-like substituents show no appreciable effect on the amine reactivity, as compared to common alkyl groups.
• The Absolute Configurations of Some Simple Norbornane Derivatives. A Test of the “Conformational Asymmetry” Model^1a
  作者：Jerome A. Berson、Jasjit Singh Walia、Allen Remanick、Shigeto Suzuki、P. Reynolds-Warnhoff、David Willner

  DOI：10.1021/ja01480a012

  日期：1961.10
• ——
  作者：A. O. Kas'yan、E. A. Golodaeva、A. V. Tsygankov、L. I. Kas'yan

  DOI：10.1023/a:1022553832553

  日期：——

  Reactions of p-nitrophenyloxirane with amines containing fragments with bicyclic skeleton of norbornene, norbornane, epoxynorbornane (stereoisomeric exo- and endo-5-an-aminomethylbicyclo[2.2.1]hept-2-enes, N-benzyl-endo-5-aminomethylbicyclo[2.2.1]hept-2-ene, endo-5-(2-aminoethyl)bicyclo[2.2.1]hept-2-ene, stereoisomeric exo- and endo-2-aminomethylbicyclo[2.2.1]beptanes, 2-(1-aminoethyl)bicyclo[2.2.1]heptane, exo-5-aminomethyl-exo-2,3-epoxybicyclo[2.2.1]heptane) were investigated. The aminolysis of p-nitrophenyloxirane occurred regioselectively according to Krasusky rule as was proved by H-1 and C-13 NMR data. As shown by H-1 and C-13 NMR spectroscopy the oxyalkylation product obtained from N-benzyl-endo-5-aminomethylbicyclo[2.2.1]hept-2-ene was composed of two diastereomers originating from the presence of a chiral nitrogen atom in the rear part of the rigid bicyclic skeleton. New products of amino groups transformation in the molecules of hydroxyamines were obtained by reaction with p-methylbenzoyl chloride and p-nitrophenylsulfonyl chloride. Regioselectivity of the attack of electrophilic reagents on the nitrogen in the hydroxyamines was confirmed by IR and H-1 NMR spectra of the products. The data on pharmacological activity tests of N-2-hydroxyethyl(p-nitrophenyl)-5-aminomethylbicyclo[2.2.1]hept-2-ene are reported.
• Kas'yan; Krasnovskaya; Zlenko, Russian Journal of Organic Chemistry, 1996, vol. 32, # 8, p. 1113 - 1121
  作者：Kas'yan、Krasnovskaya、Zlenko、Okovityi、Kas'yan

  DOI：——

  日期：——