diethyl cyclohexane-trans-1,2-dicarboxylate | 96836-97-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl cyclohexane-trans-1,2-dicarboxylate
• 英文别名: diethyl trans-1,2-cyclohexanedicarboxylate；diethyl 1,2-cyclohexanedicarboxylate；diethyl cyclohexane-1,2-dicarboxylate；(+/-)-trans-cyclohexane-1,2-dicarboxylic acid diethyl ester；(+/-)-trans-Cyclohexan-dicarbonsaeure-(1.2)-diaethylester；(+/-)-trans-Cyclohexan-1,2-dicarbonsaeure-diaethylester；diethyl (1S,2S)-cyclohexane-1,2-dicarboxylate
• CAS: 96836-97-4
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: ZTUZDYWYNQDJKR-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl cyclohexane-trans-1,2-dicarboxylate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 trans-1,2-bis(hydroxymethyl)cyclohexane di-p-toluene-sulfonate
  参考文献：
  名称：

  Conformational equilibrium in 8-methyl-cis-2-thiahydrindane and 8-methyl-cis-2-oxahydrindane by13C NMR spectroscopy

  摘要：

  AbstractThe preferred conformation of 8‐methyl‐cis‐thiahydrindane has been both estimated by 13C NMR chemical shifts and determined by low temperature 13C NMR spectroscopy to be the conformer with the methyl group equatorial with respect to the cyclohexane ring. This result is in disagreement with the interpretation of the temperature dependence of the CD spectra of (+) and (−) 8‐methyl‐cis‐2‐thiahydrindane, whereby the conformation with the methyl group axial with respect to the cyclohexane ring was claimed to be the preferred conformation. The preferred conformation of the related oxygen heterocycle, 8‐methyl‐cis‐2‐oxahydrindane, has been estimated by 13C NMR chemical shifts to be the conformer with the methyl group axial with respect to the cyclohexane ring. Possible reasons for these observations are discussed.

  DOI：

  10.1002/mrc.1270160403
• 作为产物：
  描述：

  trans-1,2-bis(ethoxycarbonyl)-4-cyclohexene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 diethyl cyclohexane-trans-1,2-dicarboxylate
  参考文献：
  名称：

  Conformational equilibrium in 8-methyl-cis-2-thiahydrindane and 8-methyl-cis-2-oxahydrindane by13C NMR spectroscopy

  摘要：

  AbstractThe preferred conformation of 8‐methyl‐cis‐thiahydrindane has been both estimated by 13C NMR chemical shifts and determined by low temperature 13C NMR spectroscopy to be the conformer with the methyl group equatorial with respect to the cyclohexane ring. This result is in disagreement with the interpretation of the temperature dependence of the CD spectra of (+) and (−) 8‐methyl‐cis‐2‐thiahydrindane, whereby the conformation with the methyl group axial with respect to the cyclohexane ring was claimed to be the preferred conformation. The preferred conformation of the related oxygen heterocycle, 8‐methyl‐cis‐2‐oxahydrindane, has been estimated by 13C NMR chemical shifts to be the conformer with the methyl group axial with respect to the cyclohexane ring. Possible reasons for these observations are discussed.

  DOI：

  10.1002/mrc.1270160403

文献信息

• [EN] NEW COMPOUNDS FOR THE TREATMENT OF CNS DISORDERS<br/>[FR] NOUVEAUX COMPOSÉS POUR LE TRAITEMENT DE TROUBLES DU SNC
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011018495A1

  公开（公告）日：2011-02-17

  The invention relates to novel pyrazolopyrimidinones according to formula (I). The new compounds shall be used for the manufacture of medicaments, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. The new compounds are also for the manufacture of medicaments for the treatment of Alzheimer's disease. Further aspects of the present invention refer to a process for the manufacture of the compounds and their use for producing medicaments.

  该发明涉及根据式(I)的新型吡唑吡嘧啶酮。新化合物应用于制造药物，特别是用于治疗感知、注意力、学习或记忆缺陷相关疾病的药物。新化合物还用于制造治疗阿尔茨海默病的药物。本发明的进一步方面涉及制造这些化合物的方法以及它们用于制造药物的用途。
• NEW COMPOUNDS FOR THE TREATMENT OF CNS DISORDER
  申请人：HEINE Niklas

  公开号：US20110212960A1

  公开（公告）日：2011-09-01

  The invention relates to novel pyrazolopyrimidinones according to formula (I). The new compounds shall be used for the manufacture of medicaments, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. The new compounds are also for the manufacture of medicaments for the treatment of Alzheimer's disease. Further aspects of the present invention refer to a process for the manufacture of the compounds and their use for producing medicaments.

  该发明涉及根据式(I)的新型吡唑吡嘧啶酮。这些新化合物将用于制造药物，特别是用于治疗涉及感知、注意力、学习或记忆缺陷的药物。这些新化合物还将用于制造治疗阿尔茨海默病的药物。本发明的进一步方面涉及制造这些化合物的过程以及它们用于生产药物的用途。
• Synthesis of 1,4-Cyclohexanedimethanol, 1,4-Cyclohexanedicarboxylic Acid and 1,2-Cyclohexanedicarboxylates from Formaldehyde, Crotonaldehyde and Acrylate/Fumarate
  作者：Yancheng Hu、Zhitong Zhao、Yanting Liu、Guangyi Li、Aiqin Wang、Yu Cong、Tao Zhang、Feng Wang、Ning Li

  DOI：10.1002/anie.201801287

  日期：2018.6.4

  4‐cyclohexanedicarboxylic acid (CHDA), and 1,2‐cyclohexanedicarboxylates—have been prepared by a new strategy. The synthetic processes involve a proline‐catalyzed formal [3+1+2] cycloaddition of formaldehyde, crotonaldehyde, and acrylate (or fumarate). CHDM is produced after a subsequent hydrogenation step over a commercially available Cu/Zn/Al catalyst and a one‐pot hydrogenation/oxidation/hydrolysis process yields

  通过一种新策略可以制备出有价值的聚酯单体和增塑剂-1,4-环己烷二甲醇（CHDM），1,4-环己烷二羧酸（CHDA）和1,2-环己烷二羧酸酯。合成过程涉及甲醛，巴豆醛和丙烯酸酯（或富马酸酯）的脯氨酸催化的正式[3 + 1 + 2]环加成反应。CHDM是在随后的商业化Cu / Zn / Al催化剂上进行加氢步骤后产生的，单锅加氢/氧化/水解过程可生成CHDA，而1,2-环己烷二羧酸盐则是通过Pd / C催化的串联脱羰/氢化步骤。
• Olefin Polymerisation Catalyst Containing a Cycloakane Dicarboxylate as Electron Donor
  申请人：Ernst Andreas B.

  公开号：US20080113860A1

  公开（公告）日：2008-05-15

  A catalyst system useful in polymerizing olefins comprising a solid, hydrocarbon-insoluble catalyst component containing magnesium, titanium and halogen and an internal or external electron donor comprising a substituted hydrocarbyl four to eight-membered cycloalkane dicarboxylate wherein the substituents are positioned on the cycloalkane to place the dicarboxylate groups into adjacent conformational positions and wherein the substitutes contain 1 to 20 carbon atoms and may be joined to the cycloalkane structure to form a bicyclo structure.

  一种用于聚合烯烃的催化剂系统，包括固体、烃类不溶性催化剂组分，其中包含镁、钛和卤素，以及内部或外部电子给体，包括取代的烃基四至八元环二羧酸酯，其中取代基位于环烷烃上，以使二羧酸酯基团处于相邻的构象位置，并且取代基含有1至20个碳原子，并且可以连接到环烷烃结构上形成双环结构。
• A Metal-Free Cyclobutadiene Reagent for Intermolecular [4 + 2] Cycloadditions
  作者：Benjamin R. Boswell、Carl M. F. Mansson、Gabrielle E. Cabrera、Calvin R. Hansen、Allen G. Oliver、Noah Z. Burns

  DOI：10.1021/jacs.3c01591

  日期：2023.3.15

  due to its lengthy synthesis that generates hazardous byproducts including excess heavy metals. Herein, we report a scalable, metal-free cyclobutadiene reagent, diethyldiazabicyclohexene dicarboxylate, and explore its intermolecular [4 + 2] cycloaddition with various electron-deficient alkenes. We also demonstrate its utility in a three-step synthesis of dipiperamide G and a diverse array of product derivatizations

  环丁二烯是一种高反应性抗芳烃，60 多年来一直令化学家着迷。然而，它在化学合成中的制备和使用很少，部分原因是它的合成过程冗长，会产生包括过量重金属在内的有害副产物。在此，我们报道了一种可扩展的、不含金属的环丁二烯试剂二乙基二氮杂双环己烯二羧酸盐，并探索了它与各种缺电子烯烃的分子间 [4 + 2] 环加成反应。我们还证明了它在双哌酰胺 G 的三步合成和包括溴环丁二烯在内的多种产品衍生化中的实用性。