((1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-en-2-yl)methanol | 116126-88-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-en-2-yl)methanol
• 英文别名: 2-methylbicyclo[2.2.1]hept-5-ene-2-methanol；[(1R,2S,4R)-2-methyl-2-bicyclo[2.2.1]hept-5-enyl]methanol
• CAS: 116126-88-6
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: WNHHRXSVKWWRJY-HRDYMLBCSA-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：

  ((1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-en-2-yl)methanol 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,4R)-2-methylbicyclo[2.2.1]hept-5-ene-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：

  (1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde 在 sodium tetrahydroborate 作用下， 生成 ((1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-en-2-yl)methanol
  参考文献：
  名称：

  Strained silacycle-catalyzed asymmetric Diels–Alder cycloadditions: the first highly enantioselective silicon Lewis acid catalyst

  摘要：

  The first highly enantioselective silicon Lewis acid catalyst for an asymmetric organic transformation has been developed. The catalyst derives its activity from the strain induced in the silicon center by virtue of being constrained in a five-membered ring. A simple tridentate ligand has been developed and the derived chlorosilane complex catalyzes the Diels-Alder cycloaddition of methacrolein and cyclopentadiene with 94% ee. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.076

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。
• 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。
• NORBORNENE-TYPE POLYMERS HAVING QUATERNARY AMMONIUM FUNCTIONALITY
  申请人：Bell Andrew

  公开号：US20110143260A1

  公开（公告）日：2011-06-16

  Embodiments of the present disclosure encompass vinyl addition and ROMP polymers having at least one type of repeating unit that encompasses a comprise N + (CH 3 ) 3 OH − moiety. Other embodiments in accordance with the disclosure include alkali anion-exchange membranes (AAEMs) made from one of such polymers, anion fuel cells (AFCs) that encompass such AAEMs and components of such AFCs, other than the AAEM, that encompass one of such polymers.

  本公开的实施例涵盖具有至少一种重复单元的乙烯加成和ROMP聚合物，该重复单元包括一个包含N+（CH3）3OH−基团的组分。根据本公开的其他实施例，还包括由此类聚合物之一制成的碱性阴离子交换膜（AAEMs），包括这样的AAEM的阴离子燃料电池（AFCs）以及包括这样的聚合物之一的AFC的组件，除了AAEM。
• 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：——