2-oxohexahydropentalene-3a-carboxylic acid ethyl ester | 24778-84-5

• 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-oxohexahydropentalene-3a-carboxylic acid ethyl ester
• 英文别名: ethyl 3-oxobicyclo<3.3.0>octane-1β-carboxylate；2-oxooctahydropentalene-3a-carboxylic acid ethyl ester；1-Aethoxycarbonyl-7-oxo-cis-bicyclo<3.3.0>octan；ethyl (3aS,6aS)-5-oxo-1,2,3,4,6,6a-hexahydropentalene-3a-carboxylate
• CAS: 24778-84-5
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: HMRSZXZQFBSDSO-KWQFWETISA-N

物化性质

• 沸点：
  279.8±23.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  2-oxohexahydropentalene-3a-carboxylic acid ethyl ester 在 sodium tetrahydroborate 、 水 、 三溴化磷 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 9.0h， 生成 ethyl 3-cyano-cis-bicyclo<3.3.0>octane-1-carboxylate
  参考文献：
  名称：

  Bhattacharya; Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 10, p. 903 - 910

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氧代环戊基乙酸乙酯 在 硫酸 作用下， 生成 2-oxohexahydropentalene-3a-carboxylic acid ethyl ester
  参考文献：
  名称：

  脂环族化合物-IV：碱对某些双环和单环酮糖基化物的作用

  摘要：

  三环环丙基酮（VIA，B）不能被碱异构化成环链二烯酮。单环甲苯磺酸盐（XXIX和XXII）没有以其十氢萘酸和八氢萘类似物（I和XX）的方式反应。

  DOI：

  10.1016/0040-4020(69)80050-5

文献信息

• Approaches to novel bicarbocyclic nucleosides
  作者：Qi Chao、Vasu Nair

  DOI：10.1016/0040-4039(95)01545-0

  日期：1995.10

  Approaches to the synthesis of a novel family of carbocyclic nucleosides of potential anti-HIV interest have been developed. The key carbocyclic intermediate 9 was coupled with desired heterocyclic bases to give the corresponding bicyclic nucleosides. The structure of compound 9 and the bicarbocyclic dideoxynucleosides were confirmed by extensive 1H and 13C NMR studies including COSY, NOESY, DEPT and

  已经开发了潜在的抗HIV兴趣的新型碳环核苷家族的合成方法。将关键的碳环中间体9与所需的杂环碱基偶联，得到相应的双环核苷。通过广泛的1 H和13 C NMR研究（包括COSY，NOESY，DEPT和选择性INEPT实验），证实了化合物9和双碳环双脱氧核苷的结构。
• β Elimination of a phosphonate group from an alkoxyl radical — Intramolecular acylation using acylphosphonate derivatives as carbonyl group acceptors
  作者：Chang Ho Cho、Sunggak Kim

  DOI：10.1139/v05-099

  日期：2005.6.1

  possibility of β elimination of a phosphonate group in radical reactions was studied. The facile β elimi- nation of the phosphonate group from an alkoxyl radical was observed for the first time, whereas the β elimination of the phosphonate group from an aminyl and an alkyl radical did not occur. On the basis of our findings, the use of an acylphosphonate as a carbonyl group radical acceptor was investigated.

  研究了自由基反应中膦酸酯基团 β 消除的可能性。首次观察到从烷氧基自由基轻松β消除膦酸酯基团，而未发生从氨基和烷基自由基β消除膦酸酯基团。基于我们的发现，研究了使用酰基膦酸酯作为羰基自由基受体。在苯中的六甲基二锡存在下，在 300 nm 处，酰基膦酸酯的自由基环化，以高产率获得 ac yclopentanone 或环己酮衍生物，而不会形成直接还原产物。该反应可以在类似条件下在催化量的六甲基二锡（0.2当量）存在下进行。此外，烷基膦酰硫代甲酸酯基团可以作为烷基硫代羰基基团等价的自由基受体，为硫代内酯的合成提供了方便的途径。简历 : 在一个 etudie la possibilite d'une 消除 β d'un groupe phosphonate au cours de reactor radicalaires。在观察上，pour la Premiere fois une 消除 β facile
• Synthesis of bicarbocyclic dideoxynucleosides as potential antiviral agents
  作者：Qi Chao、Vasu Nair

  DOI：10.1016/s0040-4020(96)01137-4

  日期：1997.2

  Two novel classes of bicarbocyclic dideoxynucleosides have been synthesized for antiviral studies. The key intermediates, 9 and 23, synthesized in multiple steps from readily available monocyclic or bicyclic precursors, were coupled with the desired heterocyclic bases to afford, after further elaboration, the corresponding bicarbocyclic dideoxynucleosides. The structure and stereochemistry of the tosylate intermediates and the target bicarbocyclic dideoxynucleosides were confirmed by extensive H-1 and C-13 NMR studies including COSY, NOESY, DEFT, and selective INEPT experiments. (C) 1997, Elsevier Science Ltd.
• β-Elimination of a Phosphonate Group from an Alkoxy Radical:  An Intramolecular Acylation Approach Using an Acylphosphonate as a Carbonyl Group Acceptor
  作者：Sunggak Kim、Chang Ho Cho、Chae Jo Lim

  DOI：10.1021/ja036499p

  日期：2003.8.1

  On the basis of facile beta-elimination of a phosphonate group from an alkoxy radical, intramolecular acylation reaction has been developed, in which an acylphosphonate is used as an excellent carbonyl group radical acceptor.
• Novel 2-aminooctahydrocyclopentalene-3a-carboxamides as potent CCR2 antagonists
  作者：Chaozhong Cai、Fu-An Kang、Cuifen Hou、John C. O’Neill、Evan Opas、Sandra McKenney、Dana Johnson、Zhihua Sui

  DOI：10.1016/j.bmcl.2012.10.069

  日期：2013.1

  Novel CCR2 antagonists with a novel 2-aminooctahydrocyclopentalene-3a-carboxamide scaffold were designed. SAR studies led to a series of potent compounds. For example, compound 51 had a good PK profile in both dog and monkey, and exhibited excellent efficacy when dosed orally in an inflammation model in hCCR2 KI mice. In addition, an asymmetric synthesis to the core structures was developed. (C) 2012 Elsevier Ltd. All rights reserved.