2-Methyl-2-endo-hydroxymethyl-bicyclo<2.2.1>hepten-(5) | 58055-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methyl-2-endo-hydroxymethyl-bicyclo<2.2.1>hepten-(5)
• 英文别名: (+/-)-2-exo-Methyl-2-endo-hydroxymethyl-norbornen-(5)；[(1R,2R,4R)-2-methyl-2-bicyclo[2.2.1]hept-5-enyl]methanol
• CAS: 58055-94-0；58055-95-1；74039-17-1；91605-21-9；116126-88-6；139402-56-5
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: WNHHRXSVKWWRJY-VGMNWLOBSA-N

物化性质

• 熔点：
  89-91 °C
• 沸点：
  193.7±9.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

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：

  2-Methyl-2-endo-hydroxymethyl-bicyclo<2.2.1>hepten-(5) 在 Lindlar's catalyst 氢气 作用下， 以 乙醇 为溶剂， 生成 ((1S,2R,4R)-2-Methyl-bicyclo[2.2.1]hept-2-yl)-methanol
  参考文献：
  名称：

  自行车双子星– X响尾蛇与降冰片—III

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(01)82460-1
• 作为产物：
  描述：

  (2-exo)-methylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2-Methyl-2-endo-hydroxymethyl-bicyclo<2.2.1>hepten-(5)
  参考文献：
  名称：

  自行车双子星– X响尾蛇与降冰片—III

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(01)82460-1

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。
• Lewis acid mediated asymmetric Diels–Alder reactions of chiral 2-phosphonoacrylates
  作者：Jia-Liang Zhu、Po-Erh Chen、Hue-Wen Huang

  DOI：10.1016/j.tetasy.2012.11.021

  日期：2013.1

  2-Phosphonoacrylates containing four chiral alcohol auxiliaries were efficiently prepared and evaluated in Lewis acid mediated Diels–Alder reactions. Under the activation of SnCl4, all reactions performed in CH2Cl2 at −65 °C exclusively afforded the endo (endo-to-carboxylate) cycloadducts with dr’s ranging from 50:50 to >99:1. The best facial selectivity was obtained from the substrate bearing a (−)-phenylmenthyl

  含有四种手性醇助剂的2-膦酸酯已通过路易斯酸介导的Diels-Alder反应进行了高效制备和评估。在SnCl 4的激活下，在CH 2 Cl 2中于-65°C进行的所有反应仅得到dr's为50:50至> 99：1的内（内-羧化）环加合物。从带有（-）-苯基薄荷基的底物获得最佳的面部选择性，得到的加合物为（dr> 99：1）或几乎为（dr = 99：1）单一非对映异构体。描述了用于阐明环加合物的结构以及观察到的立体选择性的合理化的详细策略。
• 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
• 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.
• GIESE B.; HEUCK K., CHEM. BER., 1981, 114, NO 4, 1572-1575
  作者：GIESE B.、 HEUCK K.

  DOI：——

  日期：——