2-Oxo-2,3,4,4a,5,6,7,8-octahydro-4a-naphthalincarbonsaeureaethylester | 68235-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Oxo-2,3,4,4a,5,6,7,8-octahydro-4a-naphthalincarbonsaeureaethylester
• 英文别名: (S)-ethyl 3,4,5,6,7,8-hexahydro-2-oxo-4a(2H)-naphthalene carboxylate；ethyl (4aS)-7-oxo-1,2,3,4,5,6-hexahydronaphthalene-4a-carboxylate
• CAS: 68235-48-3
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: SRDFWBNFGXTHOY-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  甲基三苯基溴化膦 、 2-Oxo-2,3,4,4a,5,6,7,8-octahydro-4a-naphthalincarbonsaeureaethylester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.0h， 生成 (S)-(-)-ethyl 3,4,5,6,7,8-hexahydro-2-methylene-4a(2H)-naphthalene carboxylate
  参考文献：
  名称：

  Facile Enantioselective Synthesis of Two New Bicyclic Chiral Templates

  摘要：

  Optically active bicyclic dienes, 4 and 5 have been enantioselectively prepared in three and four steps, respectively. Mixtures of predominantly either the R or S enantiomer were obtained via an asymmetric alkylation of a chiral enamine.

  DOI：

  10.1080/00397919508011379
• 作为产物：
  描述：

  ethyl (S)-2-oxo-1-(3-oxobutyl)-cyclohexanecarboxylate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 2-Oxo-2,3,4,4a,5,6,7,8-octahydro-4a-naphthalincarbonsaeureaethylester
  参考文献：
  名称：

  Facile Enantioselective Synthesis of Two New Bicyclic Chiral Templates

  摘要：

  Optically active bicyclic dienes, 4 and 5 have been enantioselectively prepared in three and four steps, respectively. Mixtures of predominantly either the R or S enantiomer were obtained via an asymmetric alkylation of a chiral enamine.

  DOI：

  10.1080/00397919508011379

文献信息

• Über die Stereoselektivität der α-Alkylierung von (1<i>R</i>, 2<i>S</i>) (+)-<i>cis</i>-2-hydroxy-cyclohexancarbonsäureäthylester
  作者：György Fráter

  DOI：10.1002/hlca.19800630605

  日期：1980.9.17

  The Stereoselectivity of the α-Alkylation of (+)-(1R, 2S)-cis-Ethyl-2-hydroxy-cyclohexanecarboxylate

  （+）-（1 R，2 S）-顺式-乙基-2-羟基-环己烷羧酸酯的α-烷基化的立体选择性
• Direct Generation of Nucleophilic Chiral Palladium Enolate from 1,3-Dicarbonyl Compounds:  Catalytic Enantioselective Michael Reaction with Enones
  作者：Yoshitaka Hamashima、Daido Hotta、Mikiko Sodeoka

  DOI：10.1021/ja027075i

  日期：2002.9.1

  Generation of chiral palladium enolates from 1,3-dicarbonyl compounds with the palladium aqua complex and its application to the highly efficient catalytic enantioselective Michael reaction with enones are described. The palladium aqua complexes are likely to supply Brønsted base and Brønsted acid successively during the reaction. The former activates the carbonyl compounds to give chiral palladium enolates, and the latter cooperatively activates enones. Using a catalytic amount (2-10 mol %) of the palladium complexes, the various 1,3-dicarbonyl compounds including diketones and beta-ketoesters were converted to the desired Michael adducts in good yields (69-92%) with excellent enantiomeric excesses (89-99% ee).
• FRATER G., HELV. CHIM. ACTA, 1980, 63, NO 6, 1383-1390
  作者：FRATER G.

  DOI：——

  日期：——