(1S-exo)-2-methylbicyclo<2.2.1>hept-5-ene-2-methanol | 91605-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S-exo)-2-methylbicyclo<2.2.1>hept-5-ene-2-methanol
• 英文别名: (5S)-(+)-5-methyl-5-hydroxymethylbicyclo[2.2.1]hept-2-ene；(1S,2R,4S)-2-methylbicyclo[2.2.1]hept-5-ene-2-methanol；2-endo-Methyl-2-exo-hydroxymethyl-norbornen-(5)；2-endo-Methyl-2-exo-hydroxymethyl-5-norbornen；[(1S,2R,4S)-2-methyl-2-bicyclo[2.2.1]hept-5-enyl]methanol
• CAS: 91605-21-9
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: WNHHRXSVKWWRJY-YIZRAAEISA-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：

  (1S-exo)-2-methylbicyclo<2.2.1>hept-5-ene-2-methanol 生成 5,5-dimethylbicyclo{2.2.1}hept-2-ene
  参考文献：
  名称：

  The Absolute Configurations of Some Simple Norbornane Derivatives. A Test of the “Conformational Asymmetry” Model^1a

  摘要：

  DOI：

  10.1021/ja01480a012
• 作为产物：
  描述：

  (+/-)-2-methyl-norborn-5-ene-2exo-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (1S-exo)-2-methylbicyclo<2.2.1>hept-5-ene-2-methanol
  参考文献：
  名称：

  The Absolute Configurations of Some Simple Norbornane Derivatives. A Test of the “Conformational Asymmetry” Model^1a

  摘要：

  DOI：

  10.1021/ja01480a012

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。
• 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。
• Asymmetric Diels-Alder Reaction of α-Substituted and β,β-Disubstituted α,β-Enals via Diarylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereocenters
  作者：Yujiro Hayashi、Bojan P. Bondzic、Tatsuya Yamazaki、Yogesh Gupta、Shin Ogasawara、Tohru Taniguchi、Kenji Monde

  DOI：10.1002/chem.201602345

  日期：2016.10.24

  Diels–Alder reaction of α‐substituted acrolein proceeds in the presence of the trifluoroacetic acid salt of trifluoromethyl‐substituted diarylprolinol silyl ether to afford the exo‐isomer with both excellent diastereoselectivity and high enantioselectivity. In the Diels–Alder reaction of a β,β‐disubstituted α,β‐unsaturated aldehyde, good exo‐selectivity and excellent enantioselectivity was obtained when the

  α-取代的丙烯醛的不对称Diels-Alder反应在三氟甲基取代的二芳基脯氨醇甲硅烷基醚的三氟乙酸盐存在下进行，从而提供具有优异的非对映选择性和高对映选择性的外向异构体。在β，β-二取代的α，β-不饱和醛的Diels-Alder反应中，当将三氟甲基取代的二芳基脯氨醇的大体积三异丙基甲硅烷基醚的高氯酸盐用作有机催化剂时，可获得良好的exo-选择性和出色的对映选择性。水的存在。在这两种情况下，全碳四元立体中心都是对映选择性地构建的。
• 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.