2-formylcyclopentaneacetaldehyde | 100249-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-formylcyclopentaneacetaldehyde
• 英文别名: Bis-nor-iridodial；2-(2-Oxoethyl)cyclopentane-1-carbaldehyde
• CAS: 100249-23-8
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: GMAYKUGFUHAWIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-formylcyclopentaneacetaldehyde 在 盐酸羟胺 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 6,7-二氢-5H-环戊并[c]吡啶
  参考文献：
  名称：

  Synthesis of Hexahydro-2-pyrindine (=Hexahydrocyclopenta[c]pyridine) Derivatives as Conformationally Restricted Analogs of the Nicotinic Ligands Arecolone and Isoarecolone

  摘要：

  Two hexahydropyrindine derivatives. 1,2,3,4,6,7-hexahydro-2-methyl-5H-cyclopenta[c]pyridin-5-one (1) and 1.2.3.4.5.6- hexahydro-2-methyl-7H-cyclopenta[c]pyridin-7-one (2), and their methiodides 14 and 26, respectively, were synthesized. They can be considered rigid analogues of the known nicotinic agonists arecolone (=1-( 1,2,5 6- tetrahydro-l-methylpyridin-3-yl)ethanone) and isoarecolone(= 1-( 1,2,3,6-tetrahydro-1-methylpridin-4-yl)ethanone). The affinity for the central nicotinic receptor were measured on rat cerebral cortex. Although only the methiodide 14. among the four conformationally restricted compounds, shows an appreciable affinity. the results obtained provide useful information on the molecular requirements at the interaction site of the central nicotinic receptors.

  DOI：

  10.1002/1522-2675(200201)85:1<96::aid-hlca96>3.0.co;2-7
• 作为产物：
  描述：

  ethyl 2-(2-ethoxy-2-oxoethyl)cyclopent-1-enecarboxylate 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 2-formylcyclopentaneacetaldehyde
  参考文献：
  名称：

  Synthesis of Hexahydro-2-pyrindine (=Hexahydrocyclopenta[c]pyridine) Derivatives as Conformationally Restricted Analogs of the Nicotinic Ligands Arecolone and Isoarecolone

  摘要：

  Two hexahydropyrindine derivatives. 1,2,3,4,6,7-hexahydro-2-methyl-5H-cyclopenta[c]pyridin-5-one (1) and 1.2.3.4.5.6- hexahydro-2-methyl-7H-cyclopenta[c]pyridin-7-one (2), and their methiodides 14 and 26, respectively, were synthesized. They can be considered rigid analogues of the known nicotinic agonists arecolone (=1-( 1,2,5 6- tetrahydro-l-methylpyridin-3-yl)ethanone) and isoarecolone(= 1-( 1,2,3,6-tetrahydro-1-methylpridin-4-yl)ethanone). The affinity for the central nicotinic receptor were measured on rat cerebral cortex. Although only the methiodide 14. among the four conformationally restricted compounds, shows an appreciable affinity. the results obtained provide useful information on the molecular requirements at the interaction site of the central nicotinic receptors.

  DOI：

  10.1002/1522-2675(200201)85:1<96::aid-hlca96>3.0.co;2-7

文献信息

• An unexpected inversion of enantioselectivity in the proline catalyzed intramolecular Baylis–Hillman reaction
  作者：Shang-Hung Chen、Bor-Cherng Hong、Cheng-Feng Su、Sepehr Sarshar

  DOI：10.1016/j.tetlet.2005.10.072

  日期：2005.12

  A highly enantioselective proline catalyzed intramolecular Baylis-Hillman reaction of hept-2-enedial is reported. Addition of imidazole to the mixture results in art unusual inversion of enantioselectivity. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of Hexahydro-2-pyrindine (=Hexahydrocyclopenta[c]pyridine) Derivatives as Conformationally Restricted Analogs of the Nicotinic Ligands Arecolone and Isoarecolone
  作者：Luca Guandalini、Silvia Dei、Fulvio Gualtieri、Maria Novella Romanelli、Serena Scapecchi、Elisabetta Teodori、Katia Varani

  DOI：10.1002/1522-2675(200201)85:1<96::aid-hlca96>3.0.co;2-7

  日期：2002.1

  Two hexahydropyrindine derivatives. 1,2,3,4,6,7-hexahydro-2-methyl-5H-cyclopenta[c]pyridin-5-one (1) and 1.2.3.4.5.6- hexahydro-2-methyl-7H-cyclopenta[c]pyridin-7-one (2), and their methiodides 14 and 26, respectively, were synthesized. They can be considered rigid analogues of the known nicotinic agonists arecolone (=1-( 1,2,5 6- tetrahydro-l-methylpyridin-3-yl)ethanone) and isoarecolone(= 1-( 1,2,3,6-tetrahydro-1-methylpridin-4-yl)ethanone). The affinity for the central nicotinic receptor were measured on rat cerebral cortex. Although only the methiodide 14. among the four conformationally restricted compounds, shows an appreciable affinity. the results obtained provide useful information on the molecular requirements at the interaction site of the central nicotinic receptors.