(1R-exo)-2-methylbicyclo<2.2.1>heptane-2-carboxaldehyde | 176774-77-9

• 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-carboxaldehyde
• 英文别名: 2-endo-Methylbicyclo[2.2.1]heptan-2-exo-carbonaldehyd；(1R,2R,4S)-2-methylbicyclo[2.2.1]heptane-2-carbaldehyde
• CAS: 176774-77-9
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: RKFWEHDUTACQKS-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-氯-2,4-二磺酰胺基苯胺 、 (1R-exo)-2-methylbicyclo<2.2.1>heptane-2-carboxaldehyde 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 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 、 [1R-(1α,2β(S*),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-exo)-2-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 、 sodium acetate 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 6.0h， 生成 (1R-exo)-2-methylbicyclo<2.2.1>heptane-2-carboxaldehyde
  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

• Cp*rhodium complexes with salicyloxazolines: Diastereoselective synthesis, configurational stability and use as asymmetric catalysts for a Diels–Alder reaction
  作者：Adam J. Davenport、David L. Davies、John Fawcett、David R. Russell

  DOI：10.1016/j.jorganchem.2005.10.053

  日期：2006.5

  salicyloxazolines in the presence of NaOMe gives complexes [RhCl(R-saloxaz)Cp*] (1–4) which have been fully characterised. The diastereoselectivity of complexation depends on the substituents and the absolute configuration at the metal centre is unstable in solution. Treatment of 2 with 4-methylpyridine and NaSbF6 in methanol at reflux gave [Rh(4-Mepy)(S)-iPr-saloxaz}Cp*][SbF6] (5) whilst [Rh(OH2)(Me2-saloxaz)Cp*][SbF6]

  [的RhCl的反应2的Cp *] 2（CP * =η-C 5我5），在加入NaOMe存在salicyloxazolines给出配合物[的RhCl（R-saloxaz）的Cp *]（1 - 4），其已被完全表征。络合的非对映选择性取决于取代基，并且金属中心的绝对构型在溶液中不稳定。用4-甲基吡啶和NaSbF 6在甲醇中回流处理2，得到[Rh（4-Mepy）（S）-i Pr-saloxaz} Cp *] [SbF 6 ]（5）而[Rh（OH 2）（ Me 2 -saloxaz）Cp *] [SbF 6]（6）是通过1与AgSbF 6反应制备的。三种络合物，[RhCl（Me 2 -saloxaz）Cp *]（1），[RhCl （S）-i Pr-saloxaz} Cp *]（2）和[Rh（OH 2）（Me 2 -saloxaz） Cp *] [SbF 6 ]（6）已通过X射线晶体学表征。在用AgSbF
• The Asymmetric Diels–Alder Reaction of α,β-Unsaturated Aldehydes with Dienes Using a Chiral Boron Reagent as a Catalyst
  作者：Shu Kobayashi、Masatoshi Murakami、Tsunehiro Harada、Teruaki Mukaiyama

  DOI：10.1246/cl.1991.1341

  日期：1991.8

  The asymmetric Diels–Alder reaction of α,β-unsaturated aldehydes with cyclopentadiene is catalyzed by a novel chiral boron reagent generated in situ from boron tribromide and a chiral prolinol derivative, to afford the corresponding adducts in good yields with fairly good to excellent ees.

  α,β-不饱和醛与环戊二烯的不对称 Diels-Alder 反应由三溴化硼和手性脯氨醇衍生物原位生成的新型手性硼试剂催化，以良好的收率提供相应的加合物，具有相当好的到优异的 ees。
• Beckmann; Bamberger, Justus Liebigs Annalen der Chemie, 1953, vol. 580, p. 198,201
  作者：Beckmann、Bamberger

  DOI：——

  日期：——
• Structures of the .gamma.-lactones from the acid-catalyzed cyclization of exo- and endo-2-methylnorbornene-2-carboxylic acid
  作者：Robert M. Moriarty、Chung C. Chien、Timothy B. Adams

  DOI：10.1021/jo01327a037

  日期：1979.6
• 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.