6-oxo-1-cyclohexene-1-carboxylic acid tert-butyl ester | 119728-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-oxo-1-cyclohexene-1-carboxylic acid tert-butyl ester
• 英文别名: tert-Butyl 6-oxo-1-cyclohexenecarboxylate；tert-butyl 6-oxocyclohex-1-enecarboxylate；Tert-butyl 6-oxocyclohexene-1-carboxylate
• CAS: 119728-88-0
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: HNYNHMLWIZLPRL-UHFFFAOYSA-N

物化性质

• 沸点：
  294.1±39.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  6-oxo-1-cyclohexene-1-carboxylic acid tert-butyl ester 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2-Allyl-6-oxo-cyclohexanecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Remote steric effects in the Sakurai reaction

  摘要：

  A remote steric effect in the Sakurai addition to unsaturated esters containing small to large arkyl groups has been detected which leads to either cyclobutane or allyl adducts. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01703-7
• 作为产物：
  描述：

  tert-Butyl 7,7-(1,2-ethylenedioxy)-3-oxohexanoate 在 溶剂黄146 作用下， 反应 30.0h， 以81%的产率得到6-oxo-1-cyclohexene-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Facile and Efficient Preparation of Alkyl 6-Oxo-1-cyclohexenecarboxylates

  摘要：

  从乙酰乙酸甲酯及其同系物开始，通过两个步骤合成了 6-氧代-1-环己烯羧酸烷基酯，总产率从好到高。

  DOI：

  10.1055/s-1988-27675

文献信息

• Bicyclo[3.2.0]heptane-Based Enamides by Ru/PNNP-Catalyzed Enantioselective Ficini Reactions: Scope and Application in Ligand Design
  作者：Antonio Mezzetti、Christoph Schotes、Raphael Bigler

  DOI：10.1055/s-0031-1289679

  日期：2012.2

  converted into highly modular diene, phosphite-alkene, and diphosphite derivatives, which were tested as bidentate ligands with Rh(I), Ir(I), and Pd(II). asymmetric catalysis - biaryls - cycloaddition - bicyclic compounds - ligands - phosphorus - ruthenium

  从[RuCl 2（PNNP）]中提取双氯化物[PNNP =（S，S）-N，N'-双[ o-（二苯基膦基）亚苄基]环己烷-1,2-二胺]给出了难以确定的双阳离子加合物[Ru（ OEt）2（PNNP）] 2+催化环状亚烷基β-酮酯与各种炔酰胺的[2 + 2]环加成反应，从而以高收率和对映选择性生产基于双环[3.2.0]庚烷的酰胺。讨论了这些产品的结构特征，并将选定的实例转换为高度模块化的二烯，亚磷酸酯-烯烃和二亚磷酸酯衍生物，将其作为Rh（I），Ir（I）和Pd（II）的双齿配体进行了测试。 不对称催化-联芳基-环加成-双环化合物-配体-磷-钌
• Catalytic Enantioselective Vinylogous Mukaiyama–Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters
  作者：Xavier Jusseau、Pascal Retailleau、Laurent Chabaud、Catherine Guillou

  DOI：10.1021/jo3020648

  日期：2013.3.15

  The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a gamma-butenolide or gamma-lactone connected to a cycloalkane or cycoalkene moiety.
• Transition-Metal-Mediated <i>Exo</i>-Selective Diels−Alder Reactions for the Preparation of Octalones with Unusual Stereochemistries. Reactions of 2-Cobaloxime-Substituted 1,3-Dienes with Cyclohexenones in Thermal and Lewis Acid-Catalyzed [4 + 2] Cycloadditions
  作者：B. Matthew Richardson、Mark E. Welker

  DOI：10.1021/jo962076c

  日期：1997.3.1

  2-Cobaloxime-(E)-1,3-pentadienyl complexes (cobaloxime = pyridine(dimethylglyoxime)(2)cobalt(III)) react with a variety of cyclohexenones in [4 + 2] cycloaddition reactions. These cycloaddition reactions produce octalones with cis ring junctions through exo transition states. The octalones are removed from the cobalt via demetalation reactions that replace the cobalt with a hydrogen and provide pyr(dmg)(2)CoMe, which can be recycled into the synthesis of the starting dienyl complex.