(5R)-(+)-5-methyl-5-hydroxymethylbicyclo[2.2.1]hept-2-ene | 162868-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R)-(+)-5-methyl-5-hydroxymethylbicyclo[2.2.1]hept-2-ene
• 英文别名: (1S-endo)-2-methylbicyclo<2.2.1>hept-5-ene-2-methanol；[(1S,2S,4S)-2-methyl-2-bicyclo[2.2.1]hept-5-enyl]methanol
• CAS: 162868-71-5
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: WNHHRXSVKWWRJY-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (5R)-(+)-5-methyl-5-hydroxymethylbicyclo[2.2.1]hept-2-ene 在 palladium on activated charcoal 氢气 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 2.0h， 生成 (1R,2S,4S)-2-methylbicyclo[2.2.1]heptane-2-carbaldehyde
  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：

  1-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3$l^{6-thia-4-azatricyclo[5.2.1.0^{1,5]decan-4-yl]-2-methylprop-2-en-1-one 生成 (5R)-(+)-5-methyl-5-hydroxymethylbicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Oppolzer Wolfgang, Seletsky Boris M., Bernardinelli Gerald, Tetrahedron Lett, 35 (1994) N 21, S 3-5

  摘要：

  DOI：

文献信息

• An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels–Alder reactions
  作者：Douglas P Heller、Daniel R Goldberg、Hongqiao Wu、William D Wulff

  DOI：10.1139/v06-124

  日期：2006.10.1

  Several derivatives of the vaulted biaryl ligand VAPOL were prepared and evaluated as chiral ligands for aluminum Lewis acids in the catalytic asymmetric Diels–Alder reactions of methyl acrylate an...

  制备了拱形联芳基配体 VAPOL 的几种衍生物，并将其作为路易斯酸铝的手性配体在丙烯酸甲酯和...的催化不对称 Diels-Alder 反应中进行评估。
• Asymmetric Diels-Alder reactions of chiral N-methacryloylsultams with 1,3-dienes
  作者：Wolfgang Oppolzer、Boris M. Seletsky、Gérald Bernardinelli

  DOI：10.1016/s0040-4039(00)73222-9

  日期：1994.5

  undergoes efficient, endo-selective and highly diastereoface controlled [4+2]-additions to cyclopentadiene, isoprene, (E)-piperylene and the 2-silyloxydienes 10 and 12. The resulting crystalline cycloadducts are smoothly reduced with LiAlH4 providing the recovered auxiliary and the corresponding enantiomerically pure alcohols.

  R 2 AlCl配位的N-甲基丙烯酰胺基1c经过高效，内选择性和高度非对映体控制的[4 + 2]加成到环戊二烯，异戊二烯，（E）-亚戊二烯和2-甲硅烷基氧二烯10和12上。用LiAlH 4平滑地还原所得的结晶环加合物，提供了回收的助剂和相应的对映体纯的醇。
• ——
  作者：E.G. Mamedov

  DOI：10.1023/a:1012374828303

  日期：——

  An asymmetrical synthesis of bicyclo[2.2.1]hept-2-enes is described performed by [4+21-cyclo-addition of (-)-menthyl acrylate and (-)-menthyl methacrylate to cyclopentadiene in the presence of BBr3. The effect of different factors on isomer composition, yield, and enantiomeric purity of the compounds obtained was investigated. Kovatch indices were determined and boiling points were estimated with the use of gas-liquid chromatography.
• Oppolzer Wolfgang, Seletsky Boris M., Bernardinelli Gerald, Tetrahedron Lett, 35 (1994) N 21, S 3-5
  作者：Oppolzer Wolfgang, Seletsky Boris M., Bernardinelli Gerald

  DOI：——

  日期：——
• Enantioselective Synthesis of Cyclothiazide Analogues:  Novel Probes of the Stereospecific Actions of Benzothiadiazines at AMPA-Type Glutamate Receptors
  作者：Yuefei Hu、Kelvin A. Yamada、David K. Chalmers、Durga P. Annavajjula、Douglas F. Covey

  DOI：10.1021/ja9525317

  日期：1996.1.1

  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.