(+/-)-2-formylcyclopent-2-enecarboxylic acid | 30758-76-0

• 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: (+/-)-2-formylcyclopent-2-enecarboxylic acid
• 英文别名: 2-formylcyclopent-2-ene-1-carboxylic acid；2-formylcyclopent-2-enecarboxylic acid；2-formyl-cyclopent-2-ene-carboxylic acid；1-Formylcyclopenten-5-carbonsaeure
• CAS: 30758-76-0
• 化学式: C₇H₈O₃
• mdl: MFCD12828565
• 分子量: 140.139
• InChiKey: QMMOUMUWLXVWRW-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C
• 沸点：
  316.9±42.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-formylcyclopent-2-enecarboxylic acid 在 sodium chlorite 、 sodium dihydrogenphosphate 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 对甲苯磺酸 、 三乙胺 、 间苯二酚 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 5.0h， 生成 (1R)-2-cyclohexyl(ethyl)aminocarbonyl-2-cyclopentene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  New Proline Mimetics:  Synthesis of Thrombin Inhibitors Incorporating Cyclopentane- and Cyclopentenedicarboxylic Acid Templates in the P2 Position. Binding Conformation Investigated by X-ray Crystallography

  摘要：

  With the aim to prepare nonpeptidic thrombin inhibitors, the amino acids of the thrombin-inhibiting tripeptide chain D-Phe-Pro-Arg were replaced with isosteres. Arg was replaced with the more rigid P1 truncated p-amidinobenzylamine (Pab), Pro with either cyclopentane-1,2-dicarboxylic acid or cyclopentene-1,5-dicarboxylic acid, and D-Phe with a series of readily available lipophilic amines. One of the most potent compounds (25, pIC(50) = 6.01) in these series was cocrystallized with thrombin where the X-ray crystal structure provide insight to the structure-activity relationship (SAR).

  DOI：

  10.1021/jm990557t
• 作为产物：
  描述：

  7,7-二氯二环[3.2.0]庚-2-烯-6-酮 在 水 、 三乙胺 、 potassium carbonate 作用下， 以 叔丁醇 为溶剂， 反应 3.5h， 以52%的产率得到(+/-)-2-formylcyclopent-2-enecarboxylic acid
  参考文献：
  名称：

  （±）-7,7-dichlorobicyclo [3.2.0] hept-2-en-6-one的邻位取代的环戊烯和环戊烯酮

  摘要：

  （±）-7,7-二氯双环[3.2.0]庚-2-烯-6-酮在叔丁醇与水和三乙胺的混合物中溶剂化，然后依次用K 2 CO 3，NaBH 4处理，和CH 2 N 2，得到2-（羟甲基）环戊-2-烯-1-羧酸甲酯，将其进行氢化还原，环氧化，三氯乙酰亚胺化和乙酰化。2-（乙酰氧基甲基）环戊-2-烯-1-羧酸甲酯与氧化铬（VI）-3,5-二甲基吡唑配合物的烯丙基氧化得到2-（乙酰氧基甲基）-4-氧代环戊-2-烯-1-甲酸甲酯羧酸盐和甲基（1 R *，2 R *，5 R将*）-1-（羟甲基）-6-氧杂双环[3.1.0]-己烷-2-羧酸酯转化为合成脱氧entecavir和肉瘤霉素甲酯的结构单元。

  DOI：

  10.1134/s1070428015030057

文献信息

• An efficient procedure for synthesis of 2-formylcyclopent-2-enecarboxylic acid
  作者：Chaohang Xu、Wei Li、Xiaodong Jin、Guangke He、Hongjun Zhu

  DOI：10.1007/s11164-014-1719-1

  日期：2015.9

  A synthetic method for 2-formylcyclopent-2-enecarboxylic acid is described. This procedure comprises two steps. The first step is a [2 + 2] cycloaddition reaction, and the second step is a hydrolysis and ring-opening reaction. A plausible mechanism of the hydrolysis and ring-opening reaction was supposed. Then, the effects of different solvents, base mol ratio, concentration of base, and reaction temperature

  描述了2-甲酰基环戊-2-烯基羧酸的合成方法。此过程包括两个步骤。第一步是[2 + 2]环加成反应，第二步是水解和开环反应。推测是水解和开环反应的合理机理。然后，研究了不同溶剂，碱摩尔比，碱浓度和反应温度对第二步收率的影响。最后，在获得的优化条件下，获得并分离出产物，收率为59.4％，是先前报道的两倍以上。已经开发了一种改进的合成2-甲酰基环戊-2-烯羧酸的有效方法。
• Compounds having prolyl oligopeptidase inhibitory activity
  申请人：Gynther Jukka

  公开号：US20060229254A1

  公开（公告）日：2006-10-12

  A compound of formula (I), wherein X, R 1 , R 2 and R 3 are as defined in the disclosure, or a pharmaceutically acceptable salt or ester thereof, useful as a prolyl oligopeptidase inhibitor. The compounds can be used for the treatment of diseases or conditions where prolyl oligopeptidase inhibitors are indicated to be effective, for example for the treatment of neurodegenerative diseases, such as Alzheimer's disease and senile dementia.

  式(I)的化合物，其中X、R1、R2和R3如所披露的定义，或其药学上可接受的盐或酯，可用作脯氨酰寡肽酶抑制剂。这些化合物可用于治疗需要脯氨酰寡肽酶抑制剂具有疗效的疾病或情况，例如用于治疗神经退行性疾病，如阿尔茨海默病和老年性痴呆症。
• A Cyclopent-2-enecarbonyl Group Mimics Proline at the P2 Position of Prolyl Oligopeptidase Inhibitors
  作者：Elina M. Jarho、Jarkko I. Venäläinen、Juhani Huuskonen、Johannes A. M. Christiaans、J. Arturo Garcia-Horsman、Markus M. Forsberg、Tomi Järvinen、Jukka Gynther、Pekka T. Männistö、Erik A. A. Wallén

  DOI：10.1021/jm049503w

  日期：2004.11.1

  With the aim to replace the natural amino acid proline by a proline mimetic structure, a cyclopent-2-enecarbonyl moiety was studied at the P2 position of prolyl oligopeptidase (POP) inhibitors. The cyclopent-2-enecarbonyl moiety proved to be an excellent proline mimetic at the P2 position of POP inhibitors. The replacement is particularly useful when increased lipophilicity is needed.
• [EN] COMPOUNDS HAVING PROLYL OLIGOPEPTIDASE INHIBITORY ACTIVITY<br/>[FR] COMPOSES PRESENTANT UN EFFET INHIBITEUR SUR LA PROLYL-OLIGOPEPTIDASE
  申请人：ORION CORP

  公开号：WO2004060862A3

  公开（公告）日：2004-11-25
• An introduction of a pyridine group into the structure of prolyl oligopeptidase inhibitors
  作者：Elina M. Jarho、Jarkko I. Venäläinen、Juha Juntunen、A. Leena Yli-Kokko、Jouko Vepsäläinen、Johannes A.M. Christiaans、Markus M. Forsberg、Tomi Järvinen、Pekka T. Männistö、Erik A.A. Wallén

  DOI：10.1016/j.bmcl.2006.08.029

  日期：2006.11

  A series of ionizable prolyl oligopeptidase inhibitors were developed through the introduction of a pyridyl group to the P3 position of the prolyl oligopeptidase inhibitor structure. The study was performed on previously developed prolyl oligopeptidase inhibitors with proline mimetics at the P2 position. The 3-pyridyl group resulted in equipotent compounds as compared to the parent compounds. It was shown that the pyridyl group improves water solubility and, in combination with a 5(R)-tert-butyl-L-prolyl group at the P2 position, good lipophilicity can be achieved. (c) 2006 Elsevier Ltd. All rights reserved.