2β-<(carboethoxy)methyl>-3α-methylcyclopentanone | 80781-45-9

• 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: 2β-<(carboethoxy)methyl>-3α-methylcyclopentanone
• 英文别名: (2-methyl-5-oxo-cyclopentyl)-acetic acid ethyl ester；ethyl (trans-5-methyl-2-oxocyclopentyl)acetate；2β-[(carboethoxy)methyl]-3α-methylcyclopentanone；ethyl 2-[(1S,2R)-2-methyl-5-oxocyclopentyl]acetate
• CAS: 80781-45-9
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: VKORMSMVORBJKP-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2β-<(carboethoxy)methyl>-3α-methylcyclopentanone 在 草酰氯 、 碘 、 铜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Terpenic acids by cyclopentene annulation of exocyclic dienes. Synthesis of the triquinane portion of retigeranic acid

  摘要：

  DOI：

  10.1021/jo00347a031
• 作为产物：
  描述：

  methyl (1S,2R)-2-methyl-5-oxocyclopentane-1-carboxylate 在 sodium hydride 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 2β-<(carboethoxy)methyl>-3α-methylcyclopentanone
  参考文献：
  名称：

  Terpenic acids by cyclopentene annulation of exocyclic dienes. Synthesis of the triquinane portion of retigeranic acid

  摘要：

  DOI：

  10.1021/jo00347a031

文献信息

• Radical cyclization using a thioacetal group for radical generation
  作者：Atsushi Nishida、Norio Kawahara、Mayumi Nishida、Osamu Yonemitsu

  DOI：10.1016/0040-4020(96)00511-x

  日期：1996.7

  The generation and cyclization of several heterocyclic radicals were investigated. The hydrogen abstraction from 1,3-dithiane, 1,3-dithiolane, and 1,3-oxathiane rings by a benzophenone triplet generated the corresponding heterocyclic radicals, which gave the cyclized products by intramolecular addition to α,β-unsaturated esters. Diastereoselective radical cyclization using chiral acetals was also investigated

  研究了几种杂环基的产生和环化。通过二苯甲酮三联体从1,3-二硫杂环戊烷，1,3-二硫杂环戊烷和1,3-氧杂蒽环上夺氢产生了相应的杂环基，这些杂环基通过分子内加成α，β-不饱和酯而得到环化产物。还研究了使用手性缩醛的非对映选择性自由基环化。
• One-Pot Synthesis of Enantiomerically Enriched 2,3-Disubstituted Cyclopentanones via Copper-Catalyzed 1,4-Reduction and Alkylation
  作者：Jaesook Yun、Stephen L. Buchwald

  DOI：10.1021/ol015577f

  日期：2001.4.1

  [reaction: see text]. Enantiomerically enriched 2,3-disubstituted cyclopentanones were prepared via copper-catalyzed 1,4-reduction of 3-substituted cyclopentenones followed by alkylation of the resulting silyl enol ether. Using this procedure, trans-2,3-disubstituted cyclopentanones were produced in moderate to good overall yields (42-67%) and with excellent enantiomeric and diastereomeric excesses

  [反应：请参见文字]。通过铜催化3-取代的环戊烯酮的1，4-还原，然后将所得的甲硅烷基烯醇醚烷基化，制备对映体富集的2，3-二取代的环戊烯酮。使用该方法，以中等至良好的总收率（42-67％）以及优异的对映异构体和非对映异构体过量生产了反式2，3-二取代的环戊酮。还原和烷基化在单个反应容器中进行。
• The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction
  作者：Nathan T. Reynolds、Tomislav Rovis

  DOI：10.1016/j.tet.2005.03.121

  日期：2005.6

  A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2,3- and 2,4disubstituted cyclopentanones. The Stetter reaction of 2,5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis-diasteroiners with low ee. (c) 2005 Elsevier Ltd. All rights reserved.