(1R,2S)-2-乙氧基羰基环己烷-1-羧酸 | 76756-35-9

• 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
• 中文名称: (1R,2S)-2-乙氧基羰基环己烷-1-羧酸
• 英文名称: (1S,2R)-Cyclohexane-1,2-dicarboxylic acid monoethyl ester
• 英文别名: Ethyl hydrogen (1)-cis-cyclohexane-1,2-dicarboxylate；(1R,2S)-2-ethoxycarbonylcyclohexane-1-carboxylic acid
• CAS: 76756-35-9
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: XGRJGTBLDJAHTL-SFYZADRCSA-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：

  (1R,2S)-2-乙氧基羰基环己烷-1-羧酸 在 盐酸 、 叠氮磷酸二苯酯 、 二异丁基氢化铝 、 potassium 2-methylbutan-2-olate 、 三乙胺 作用下， 以 甲基叔丁基醚 、 水 、 甲基环己烷 、 甲苯 为溶剂， 反应 24.0h， 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：

  dl-cis-ethyl methyl cyclohexane-1,2-dicarboxylate 在 aluminum tri-bromide 、 乙硫醇 作用下， 反应 48.0h， 以80.5%的产率得到(1R,2S)-2-乙氧基羰基环己烷-1-羧酸
  参考文献：
  名称：

  Hard acid and soft nucleophile systems. 3. Dealkylation of esters with aluminum halide-thiol and aluminum halide-sulfide systems

  摘要：

  DOI：

  10.1021/jo00323a004

文献信息

• Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of<i>meso</i>Cyclic Anhydrides
  作者：Lin-Jie Yan、Hai-Feng Wang、Wen-Xue Chen、Yuan Tao、Kai-Jun Jin、Fen-Er Chen

  DOI：10.1002/cctc.201600228

  日期：2016.7.6

  chloramphenicol‐base‐derived thiourea organocatalysts, (1S,2R)‐12 a–f and (1R,2R)‐15 a–c, and their use in the enantioselective alcoholysis of meso‐anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)‐12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)‐15 a–c. This technique was used to synthesize (R)‐(−)‐baclofen

  新的氯霉素基硫脲有机催化剂（1 S，2 R）-12 a - f和（1 R，2 R）15 a - c的合成及其在介孔酸酐的对映选择性醇解中的应用描述。特别是，如果使用低负荷的（1 S，2 R）-12 a – f负载，半酯具有出色的对映选择性。使用（1 R，2 R）‐ 15 a – c几乎没有达到对映选择性。该技术用于合成（R）-（-）-baclofen。
• A family of novel bifunctional organocatalysts: Highly enantioselective alcoholysis of meso cyclic anhydrides and its application for synthesis of the key intermediate of P2X7 receptor antagonists
  作者：Hong-Jun Yang、Fang-Jun Xiong、Jie Li、Fen-Er Chen

  DOI：10.1016/j.cclet.2013.04.009

  日期：2013.7

  Abstract A family of novel squaramides/sulfamides based on 1,2-alkamine was developed as chiral bifunctional catalysts to promote the asymmetric alcoholysis of meso cyclic anhydrides. The hemiesters were obtained in high yield with up to 93% ee. The usefulness of this methodology was demonstrated in the asymmetric synthesis of the key intermediate of P2X7 receptor antagonists.

  摘要研制了一系列以1,2-链胺为基础的新型方酸/亚磺酰胺作为手性双官能催化剂，以促进内消旋环酸酐的不对称醇解。半酯以高达93％ee的高收率获得。P2X7受体拮抗剂关键中间体的不对称合成证明了该方法的有效性。
• Heterogeneous organocatalysis for the asymmetric desymmetrization of meso-cyclic anhydrides using silica gel-supported bis-cinchona alkaloids
  作者：Hyun Sook Kim、Yu-Mi Song、Jin Seok Choi、Jung Woon Yang、Hogyu Han

  DOI：10.1016/j.tet.2004.10.046

  日期：2004.12

  The silica gel-supported bis-cinchona alkaloid la was prepared and found to be an efficient heterogeneous chiral organocatalyst with high catalytic activities, enantioselectivities (up to 92% ee), and recyclability for the asymmetric desymmetrization of meso-cyclic anhydrides with alcoholysis. (C) 2004 Elsevier Ltd. All rights reserved.
• Corsano; Panizzi, Annali di Chimica, 1958, vol. 48, p. 1025,1034
  作者：Corsano、Panizzi

  DOI：——

  日期：——
• Hard acid and soft nucleophile systems. 3. Dealkylation of esters with aluminum halide-thiol and aluminum halide-sulfide systems
  作者：Manabu Node、Kiyoharu Nishide、Midori Sai、Kaoru Fuji、Eiichi Fujita

  DOI：10.1021/jo00323a004

  日期：1981.5