(1R-exo)-2-methylbicyclo<2.2.1>heptane-2-methanol | 176774-76-8

• 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: (1R-exo)-2-methylbicyclo<2.2.1>heptane-2-methanol
• 英文别名: 2-endo-Methyl-2-exo-hydroxymethyl-norbornan；[(1R,2R,4S)-2-methyl-2-bicyclo[2.2.1]heptanyl]methanol
• CAS: 176774-76-8
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: JLHGMGQPZNWAHH-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R-exo)-2-methylbicyclo<2.2.1>heptane-2-methanol 在 盐酸 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 [1R-(1α,2β(R*),4α)]-6-chloro-3,4-dihydro-3-(2-methylbicyclo[2.2.1]hept-2-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
  参考文献：
  名称：

  Enantioselective Synthesis of Cyclothiazide Analogues:  Novel Probes of the Stereospecific Actions of Benzothiadiazines at AMPA-Type Glutamate Receptors

  摘要：

  The stereospecific interactions of the eight stereoisomers of dihydromethylcyclothiazide, an analogue of cyclothiazide, with AMPA-type glutamate receptors was investigated using electrophysiological methods that measured the ability of each stereoisomer to inhibit AMPA receptor desensitization. The eight stereoisomers were obtained by HPLC separation of four pairs of enantiomerically pure (>95% ee) diastereomers prepared from (1R-exo)-, (1R-endo)-, (1S-exo)-, and (1S-endo)-2-methylbicyclo[2.2.1]heptane-2-carboxaldehyde intermediates. The desensitization process was blocked most potently by [1S-[1 alpha,2 alpha(R*),4 alpha]]-dihydromethylcyclothiazide, one of the stereoisomers prepared from the (1S-endo)-carboxaldehyde. The smallest effects on the desensitization process were found for the four stereoisomers prepared from the (1R-exo)- and (1R-endo)-carboxaldehydes. Significant differences in the ability to inhibit desensitization were observed between all diastereomer pairs except those prepared from the (1S-exo)-carboxaldehyde.

  DOI：

  10.1021/ja9525317
• 作为产物：
  描述：

  (1S,4S)-2-Methyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 碘 、 二异丁基氢化铝 、 碳酸氢钠 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 4.67h， 生成 (1R-exo)-2-methylbicyclo<2.2.1>heptane-2-methanol
  参考文献：
  名称：

  Enantioselective Synthesis of Cyclothiazide Analogues:  Novel Probes of the Stereospecific Actions of Benzothiadiazines at AMPA-Type Glutamate Receptors

  摘要：

  The stereospecific interactions of the eight stereoisomers of dihydromethylcyclothiazide, an analogue of cyclothiazide, with AMPA-type glutamate receptors was investigated using electrophysiological methods that measured the ability of each stereoisomer to inhibit AMPA receptor desensitization. The eight stereoisomers were obtained by HPLC separation of four pairs of enantiomerically pure (>95% ee) diastereomers prepared from (1R-exo)-, (1R-endo)-, (1S-exo)-, and (1S-endo)-2-methylbicyclo[2.2.1]heptane-2-carboxaldehyde intermediates. The desensitization process was blocked most potently by [1S-[1 alpha,2 alpha(R*),4 alpha]]-dihydromethylcyclothiazide, one of the stereoisomers prepared from the (1S-endo)-carboxaldehyde. The smallest effects on the desensitization process were found for the four stereoisomers prepared from the (1R-exo)- and (1R-endo)-carboxaldehydes. Significant differences in the ability to inhibit desensitization were observed between all diastereomer pairs except those prepared from the (1S-exo)-carboxaldehyde.

  DOI：

  10.1021/ja9525317

文献信息

• Bicyclische Verbindungen—X ringerweiterung von norbornanderivaten—III
  作者：W. Kraus、P. Schmutte

  DOI：10.1016/s0040-4020(01)82460-1

  日期：1968.1

  The deamination of endo- and exo-2-methyl-2-aminomethyl-norbornane with nitrous acid and the hydrolysis of endo- and exo-2-methyl-2-tosyloxymethyl-norbornane has been investigated by gas-chromatography. The ratio of tertiary methyl-bicyclo[3.2.1.]octanols-3 and -2 formed by carbon shift involving the C-1, C-2 bond and the C-2, C-3 bond, respectively, is chiefly controlled by steric factors. From the

  的脱氨基内切-和外切-2-甲基-2-氨基甲基降冰片烷与亚硝酸和的水解内切-和外切-2-甲基-2-甲苯磺酰氧基甲基降冰片烷已经通过气相色谱分析。分别通过涉及C-1，C-2键和C-2，C-3键的碳转移形成的叔甲基-双环[3.2.1。]辛醇-3和-2的比率主要受以下因素控制：空间因素。从产品组成可以得出结论，非经典的双环辛基阳离子不参与环的扩展反应。
• 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