(-)-(S)-Methyl (2-oxocyclopentyl)acetate | 49826-04-2

• 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: (-)-(S)-Methyl (2-oxocyclopentyl)acetate
• 英文别名: methyl 2-[(1S)-2-oxocyclopentyl]acetate
• CAS: 49826-04-2
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: FCUFQALZTPBXTC-LURJTMIESA-N

物化性质

• 沸点：
  227.1±13.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(S)-Methyl (2-oxocyclopentyl)acetate 在 (S)-prolinol core-containing second-generation dendrimer dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 0.8h， 以12%的产率得到trans-2-Hydroxyaethyl-cyclopentanol-2
  参考文献：
  名称：

  Asymmetric reduction of substituted indanones and tetralones catalyzed by chiral dendrimer and its application to the synthesis of (+)-sertraline

  摘要：

  A recoverable dendrimeric supported prolinol was used as a catalyst in the asymmetric reduction of indanones and tetralones to give separable cis and trans isomers up to 97% ee. This method was also applied in the enantio selective synthesis of the antidepressant drug (+)-sertraline. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.010
• 作为产物：
  描述：

  (2-氧代环戊基)-乙酸甲酯 在 2,4,6-三甲基吡啶 、 N-氯代丁二酰亚胺 、 对甲苯磺酸 、 silver nitrate 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 2.5h， 生成 (-)-(S)-Methyl (2-oxocyclopentyl)acetate
  参考文献：
  名称：

  Asymmetric acetalization: a simple method for the synthesis of chiral a-monosubstituted cyclopentanones

  摘要：

  Acetalization of alpha-monosubstituted cyclopentanones with chiral hydroxy thiols under equilibrating conditions afforded a mixture of acetals in a highly diastereoselective manner, and deacetalization of the product affords optically active alpha-monosubstituted cyclopentanones.

  DOI：

  10.1021/jo00074a002

文献信息

• Enantioselective copper-catalyzed cyclopropanation of silyl enol ethers
  作者：Alexander Ebinger、Thomas Heinz、Gisela Umbricht、Andreas Pfaltz

  DOI：10.1016/s0040-4020(98)00499-2

  日期：1998.8

  bisoxazolines are efficient catalysts for the enantioselective cyclopropanation of silyl enol ethers with diazoacetates. The resulting cyclopropanes can be converted to γ-ketocarboxylates by acid-induced ring cleavage. In this way methyl (2-oxocyclopentyl)- and (2-oxocyclohexyl)acetates have been prepared with up to 90 and 80% ee, respectively.

  衍生自半卟啉，叠氮杂菊酯和双恶唑啉的铜（I）配合物是有效的催化剂，用于将甲硅烷基烯醇醚与重氮乙酸酯进行对映选择性环丙烷化。可以通过酸诱导的环裂解将所得的环丙烷转化为γ-酮羧酸酯。以这种方式，分别以高达90％和80％的ee制备了（2-氧代环戊基）-和（2-氧代环己基）乙酸甲酯。
• Biocatalytic access to nonracemic γ-oxo esters via stereoselective reduction using ene-reductases
  作者：Nikolaus G. Turrini、Răzvan C. Cioc、Daan J. H. van der Niet、Eelco Ruijter、Romano V. A. Orru、Mélanie Hall、Kurt Faber

  DOI：10.1039/c6gc02493a

  日期：——

  The asymmetric bioreduction of [small alpha],[small beta]-unsaturated [gamma]-keto esters using ene-reductases from the Old Yellow Enzyme family proceeds with excellent stereoselectivity and high conversion levels, covering a broad range of acyclic and...

  使用Old Yellow Enzyme家族的烯键还原酶对小，小β-不饱和γ-酮酸酯进行不对称生物还原，具有出色的立体选择性和高转化率，涵盖了广泛的无环和...
• C2 Symmetric chiral N-heterocyclic carbene catalyst for asymmetric intramolecular Stetter reaction
  作者：Yasumasa Matsumoto、Kiyoshi Tomioka

  DOI：10.1016/j.tetlet.2006.06.080

  日期：2006.8

  The asymmetric intramolecular Stetter reaction of omega-formyl alpha,beta-unsaturated carbonyl compounds was catalyzed by a C2 symmetric chiral carbene, generated from (4S,5S)-diphenyl-1,3-bis(mesitylmethyl)-4,5-dihydro-1H-imidazolium tetrafluoroborate, to afford 2-substituted cyclopentanones in good enantioselectivity of up to 80%. (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric reduction of substituted indanones and tetralones catalyzed by chiral dendrimer and its application to the synthesis of (+)-sertraline
  作者：Guangyin Wang、Changwu Zheng、Gang Zhao

  DOI：10.1016/j.tetasy.2006.07.010

  日期：2006.8

  A recoverable dendrimeric supported prolinol was used as a catalyst in the asymmetric reduction of indanones and tetralones to give separable cis and trans isomers up to 97% ee. This method was also applied in the enantio selective synthesis of the antidepressant drug (+)-sertraline. (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric acetalization: a simple method for the synthesis of chiral a-monosubstituted cyclopentanones
  作者：Mayumi Nishida、Kazuyo Nakaoka、Shizuka Ono、Osamu Yonemitsu、Atsushi Nishida、Norio Kawahara、Hiroaki Takayanagi

  DOI：10.1021/jo00074a002

  日期：1993.10

  Acetalization of alpha-monosubstituted cyclopentanones with chiral hydroxy thiols under equilibrating conditions afforded a mixture of acetals in a highly diastereoselective manner, and deacetalization of the product affords optically active alpha-monosubstituted cyclopentanones.