isopropyl 3-oxocyclopent-1-ene-1-carboxylate | 122689-80-9

• 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
• 英文名称: isopropyl 3-oxocyclopent-1-ene-1-carboxylate
• 英文别名: Propan-2-yl 3-oxocyclopentene-1-carboxylate
• CAS: 122689-80-9
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: LEKFCPXASZINGP-UHFFFAOYSA-N

物化性质

• 沸点：
  241.6±29.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isopropyl 3-oxocyclopent-1-ene-1-carboxylate 在 barium dihydroxide 、 葡萄糖 、 cultures of Geotrichum candidum 、 phosphate buffer (pH: 7.0) 、 碳酸氢铵 作用下， 以 水 为溶剂， 反应 53.5h， 生成 (1S,3R)-1-氨基-1,3-环戊烷二甲酸
  参考文献：
  名称：

  化学酶促合成构象刚性的谷氨酸类似物

  摘要：

  通过微生物步骤和标准化学方法的结合，由相应的3-酮-环烷基羧酸酯合成了环己烷和谷氨酸的环戊烷衍生的类似物的所有立体异构体。

  DOI：

  10.1016/s0040-4039(00)82278-9
• 作为产物：
  描述：

  环戊基甲酰氯 在 chromium(VI) oxide 、 磷化氢 、 溴 、 乙酸酐 作用下， 以 喹啉 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 isopropyl 3-oxocyclopent-1-ene-1-carboxylate
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure isopropyl (3R)- and (3S)-3-hydroxycyclohex-1-ene-1-carboxylates and their reduction to isomers of isopropyl 3-hydroxy-cyclohexane-1-carboxylate

  摘要：

  Reduction of an alpha,beta-unsaturated cyclic ketone with Geotrichum candidum affords the corresponding (S)-allylic alcohol, while enantiospecific oxidation of the corresponding racemic alcohols leases the (R)-enantiomer unchanged, giving access to both enantiomeric forms. Subsequent chemical reduction of the double bond of these homochiral allylic alcohol allows all isomers of the corresponding cyclohexanols to be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00152-0

文献信息

• Radiolabeled HOCPCA as a highly useful tool in drug discovery and pharmacology
  作者：Nane Griem‐Krey、Bente Frølund、Aleš Marek、Petrine Wellendorph

  DOI：10.1002/jlcr.3870

  日期：2021.2

  GHB (γ-hydroxybutyrate) is not only an endogenously present small molecule but also a clinically prescribed drug for the symptomatic treatment of narcolepsy. However, GHB's mechanism of action remains to be uncovered. Within the CNS, GHB targets both GABAB receptors and a pharmacologically distinct population of high-affinity binding sites with unknown molecular identity. HOCPCA (3-hydroxycyclopent-1-enecarboxylic acid) is a structural analog of GHB selectively targeting GHB high-affinity binding sites. Here, we discuss the usefulness of 3H- and 11C-labeled HOCPCA as radioligands for selectively probing GHB high-affinity binding sites and their application in drug discovery. As such, [3H]HOCPCA's exceptional affinity and selectivity makes it an indispensable tool in drug discovery, and its utility has been demonstrated in, for example, homogenate binding studies, in vitro as well as ex vivo autoradiography. Moreover, the successful synthesis of [11C]HOCPCA is a starting point for further ligand development for future in vivo investigations of GHB high-affinity binding sites.

  GHB（γ-羟基丁酸）不仅是一种内源性的小分子，也是一种临床上用于治疗嗜睡症状的处方药。然而，GHB的作用机制仍未被揭示。在中枢神经系统中，GHB既作用于GABAB受体，也作用于一群药理学上不同的高亲和力结合位点，这些位点的分子身份尚未明确。HOCPCA（3-羟基环戊-1-烯羧酸）是GHB的结构类似物，特异性地作用于GHB的高亲和力结合位点。本文讨论了3H和11C标记的HOCPCA作为放射性配体，用于特异性地探测GHB高亲和力结合位点的效用，以及它们在药物发现中的应用。因此，[3H]HOCPCA的卓越亲和力和选择性使其成为药物发现中不可或缺的工具，其效用已在匀浆结合研究、体外及离体放射自显影中得到证明。此外，[11C]HOCPCA的成功合成是一个起点，为未来开发用于研究GHB高亲和力结合位点的配体提供了可能。
• TRIGALO, F.;BUISSON, D.;AZERAD, R., TETRAHEDRON LETT., 29,(1988) N 47, C. 6109-6112
  作者：TRIGALO, F.、BUISSON, D.、AZERAD, R.

  DOI：——

  日期：——
• Chemoenzymatic synthesis of conformationally rigid glutamic acid analogues
  作者：F. Trigalo、D. Buisson、R. Azerad

  DOI：10.1016/s0040-4039(00)82278-9

  日期：——

  All stereomers of cyclohexane and cyclopentane-derived analogues of glutamic acid have been synthesized from the corresponding 3-keto-cycloalkyl carboxylic acid esters by a combination of microbial steps and standard chemical methods.

  通过微生物步骤和标准化学方法的结合，由相应的3-酮-环烷基羧酸酯合成了环己烷和谷氨酸的环戊烷衍生的类似物的所有立体异构体。
• Chemoenzymatic synthesis of enantiopure isopropyl (3R)- and (3S)-3-hydroxycyclohex-1-ene-1-carboxylates and their reduction to isomers of isopropyl 3-hydroxy-cyclohexane-1-carboxylate
  作者：Laure Fonteneau、Sandra Rosa、Didier Buisson

  DOI：10.1016/s0957-4166(02)00152-0

  日期：2002.4

  Reduction of an alpha,beta-unsaturated cyclic ketone with Geotrichum candidum affords the corresponding (S)-allylic alcohol, while enantiospecific oxidation of the corresponding racemic alcohols leases the (R)-enantiomer unchanged, giving access to both enantiomeric forms. Subsequent chemical reduction of the double bond of these homochiral allylic alcohol allows all isomers of the corresponding cyclohexanols to be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.