(1SR,2RS,3RS,4RS)-3-(methoxycarbonyl)bicyclo[2.2.1]heptane-2-carboxylic acid

• 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: (1SR,2RS,3RS,4RS)-3-(methoxycarbonyl)bicyclo[2.2.1]heptane-2-carboxylic acid
• 英文别名: endo-3-methoxycarbonylbicyclo[2.2.1]heptane-2-exo-carboxylic acid；(1S,2R,3R,4R)-3-methoxycarbonylbicyclo[2.2.1]heptane-2-carboxylic acid
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: AIMKQBORRFFXGP-LXGUWJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1SR,2RS,3RS,4RS)-3-(methoxycarbonyl)bicyclo[2.2.1]heptane-2-carboxylic acid 以3%的产率得到
  参考文献：
  名称：

  KLUNDER, A. J. H.;VAN, GASTEL F. J. C.;ZWANENBURG, B., TETRAHEDRON LETT., 29,(1988) N 22, C. 2697-2700

  摘要：

  DOI：
• 作为产物：
  描述：

  Dimethyl norbornane-trans-2,3-dicarboxylate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以96%的产率得到(1SR,2RS,3RS,4RS)-3-(methoxycarbonyl)bicyclo[2.2.1]heptane-2-carboxylic acid
  参考文献：
  名称：

  Remote Exo/Endo Selectivity in Selective Monohydrolysis of Dialkyl Bicyclo[2.2.1]heptane-2,3-dicarboxylate Derivatives

  摘要：

  High exo-facial selectivity was observed in the selective monohydrolysis of a series of near-symmetric diesters that possess an exo-ester group and an endo-ester group attached on a norbornane or norbornene skeleton. The selectivities were found to be clear-cut, although the reaction center in these reactions is one covalent bond distant from the norbornane or norbornene ring, where the difference of the environment between the exo face and endo face is therefore expected to be negligible. The effect of the co-solvent we studied earlier for the selective monohydrolysis reaction was also confirmed and contributed to improvement of the yields of the half-esters.

  DOI：

  10.1021/jo100564e

文献信息

• Exploring the Active Conformation of Cyclohexane Carboxylate Positive Allosteric Modulators of the Type 4 Metabotropic Glutamate Receptor
  作者：Xavier Rovira、Youssef Harrak、Ana Trapero、Patricia González-Bulnes、Fanny Malhaire、Jean-Philippe Pin、Cyril Goudet、Jesús Giraldo、Amadeu Llebaria

  DOI：10.1002/cmdc.201402190

  日期：2014.12

  The active conformation of a family of metabotropic glutamate receptor subtype 4 (mGlu4) positive allosteric modulators (PAMs) with the cyclohexane 1,2‐dicarboxylic scaffold present in cis‐2‐(3,5‐dichlorophenylcarbamoyl)cyclohexanecarboxylic acid (VU0155041) was investigated by testing structurally similar six‐membered ring compounds that have a locked conformation. The norbornane and cyclohexane molecules

  一个代谢型谷氨酸受体亚型4（mGlu 4）阳性变构调节剂（PAM）家族的活性构型与顺式-2-（3,5-二氯苯基氨基甲酰基）环己烷羧酸（VU0155041）中存在的环己烷1,2-二羧酸骨架相符通过测试结构相似的具有锁定构象的六元环化合物进行了研究。设计成组mGlu降冰片烷和环己烷分子4个构象探针和对映异构体的反式非对映体进行了计算，其特征在于和组mGlu测试4药理分析。结果支持VU0155041活性构象，其中椅子环己烷在轴向位置具有芳族酰胺取代基并且在赤道位置具有羧酸盐。此外，该受体显示出手性PAM的对映体鉴别。所构建的药效团具有高度受限的mGlu 4变构结合位点，因此为mGlu 4 PAM的基于结构的药物设计迈出了一步。
• Gastel, F. J. C. van; Klunder, A. J. H.; Zwanenburg, B., Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 175 - 184
  作者：Gastel, F. J. C. van、Klunder, A. J. H.、Zwanenburg, B.

  DOI：——

  日期：——
• KLUNDER, A. J. H.;VAN, GASTEL F. J. C.;ZWANENBURG, B., TETRAHEDRON LETT., 29,(1988) N 22, C. 2697-2700
  作者：KLUNDER, A. J. H.、VAN, GASTEL F. J. C.、ZWANENBURG, B.

  DOI：——

  日期：——
• Remote Exo/Endo Selectivity in Selective Monohydrolysis of Dialkyl Bicyclo[2.2.1]heptane-2,3-dicarboxylate Derivatives
  作者：Satomi Niwayama、Hanjoung Cho、Masoud Zabet-Moghaddam、Bruce R. Whittlesey

  DOI：10.1021/jo100564e

  日期：2010.6.4

  High exo-facial selectivity was observed in the selective monohydrolysis of a series of near-symmetric diesters that possess an exo-ester group and an endo-ester group attached on a norbornane or norbornene skeleton. The selectivities were found to be clear-cut, although the reaction center in these reactions is one covalent bond distant from the norbornane or norbornene ring, where the difference of the environment between the exo face and endo face is therefore expected to be negligible. The effect of the co-solvent we studied earlier for the selective monohydrolysis reaction was also confirmed and contributed to improvement of the yields of the half-esters.