Ethyl hydrogen trans-cyclohexane-1,2-dicarboxylate | 97718-55-3

• 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: Ethyl hydrogen trans-cyclohexane-1,2-dicarboxylate
• 英文别名: (1R,2R)-2-ethoxycarbonylcyclohexane-1-carboxylic acid
• CAS: 97718-55-3
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: XGRJGTBLDJAHTL-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl hydrogen trans-cyclohexane-1,2-dicarboxylate 在 盐酸 、 叠氮磷酸二苯酯 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 作用下， 以 正己烷 、 正庚烷 、 甲基叔丁基醚 、 水 、 甲基环己烷 、 甲苯 为溶剂， 反应 21.0h， 生成 (1R,2R)-2-(benzyloxycarbonylamino)cyclohexanecarboxaldehyde
  参考文献：
  名称：

  Stereoselective Process for a CCR3 Antagonist

  摘要：

  A convergent, multikilogram, stereoselective synthesis of 1 is described. A key fragment, (S)-3-(4-fluorobenzyl)piperidine (2) was synthesized from valerolactam in three steps using our recently discovered Ir-BDPP-catalyzed asymmetric hydrogenation. Another key fragment, (IR,2R)-2-(benzyloxycarbonylamino)cyclohexanecarboxaldehyde (3) was synthesized from meso-hexahydrophthalic anhydride in seven steps. The stereochemistry was set in the first step of this sequence via a quinidine-mediated desymmetrization of the meso-anhydride. Coupling of the fragments 2 and 3 followed by deprotection provided the penultimate 23. The active pharmaceutical ingredient (API) free base I was obtained by treatment of 23 with the aminothiazole fragment 4 under mild conditions.

  DOI：

  10.1021/op050202l
• 作为产物：
  描述：

  1,2-cis-cyclohexanedicarboxylic anhydride 在 奎尼丁 、 potassium 2-methylbutan-2-olate 作用下， 以 甲苯 为溶剂， 反应 8.5h， 生成 Ethyl hydrogen trans-cyclohexane-1,2-dicarboxylate
  参考文献：
  名称：

  Stereoselective Process for a CCR3 Antagonist

  摘要：

  A convergent, multikilogram, stereoselective synthesis of 1 is described. A key fragment, (S)-3-(4-fluorobenzyl)piperidine (2) was synthesized from valerolactam in three steps using our recently discovered Ir-BDPP-catalyzed asymmetric hydrogenation. Another key fragment, (IR,2R)-2-(benzyloxycarbonylamino)cyclohexanecarboxaldehyde (3) was synthesized from meso-hexahydrophthalic anhydride in seven steps. The stereochemistry was set in the first step of this sequence via a quinidine-mediated desymmetrization of the meso-anhydride. Coupling of the fragments 2 and 3 followed by deprotection provided the penultimate 23. The active pharmaceutical ingredient (API) free base I was obtained by treatment of 23 with the aminothiazole fragment 4 under mild conditions.

  DOI：

  10.1021/op050202l

文献信息

• SULFONAMIDE DERIVATIVE AND USE THEREOF
  申请人：Fukumoto Shoji

  公开号：US20140024650A1

  公开（公告）日：2014-01-23

  Provided is a compound having an AMPA receptor function enhancing action, and useful as a prophylactic or therapeutic drug for depression, Alzheimer's disease, schizophrenia, attention deficit hyperactivity disorder (ADHD) and the like. A compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a salt thereof.

  提供了一种具有AMPA受体功能增强作用的化合物，可用作预防或治疗抑郁症、阿尔茨海默病、精神分裂症、注意力缺陷多动障碍（ADHD）等药物。该化合物由式（I）表示：其中每个符号如本说明书所定义，或其盐。
• [EN] SULFONAMIDE DERIVATIVE AND USE THEREOF<br/>[FR] DÉRIVÉ DE SULFONAMIDE ET SON UTILISATION
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2012137982A9

  公开（公告）日：2013-02-14
• US9527807B2
  申请人：——

  公开号：US9527807B2

  公开（公告）日：2016-12-27
• Stereoselective Process for a CCR3 Antagonist
  作者：Tai-Yuen Yue、Douglas D. McLeod、Kevin B. Albertson、Steven R. Beck、Joerg Deerberg、Joseph M. Fortunak、William A. Nugent、Lilian A. Radesca、Liya Tang、Cathie Dong Xiang

  DOI：10.1021/op050202l

  日期：2006.3.1

  A convergent, multikilogram, stereoselective synthesis of 1 is described. A key fragment, (S)-3-(4-fluorobenzyl)piperidine (2) was synthesized from valerolactam in three steps using our recently discovered Ir-BDPP-catalyzed asymmetric hydrogenation. Another key fragment, (IR,2R)-2-(benzyloxycarbonylamino)cyclohexanecarboxaldehyde (3) was synthesized from meso-hexahydrophthalic anhydride in seven steps. The stereochemistry was set in the first step of this sequence via a quinidine-mediated desymmetrization of the meso-anhydride. Coupling of the fragments 2 and 3 followed by deprotection provided the penultimate 23. The active pharmaceutical ingredient (API) free base I was obtained by treatment of 23 with the aminothiazole fragment 4 under mild conditions.