2-(2,2-二甲氧基乙基)环戊烷-1-酮 | 114389-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(2,2-二甲氧基乙基)环戊烷-1-酮
• 英文名称: 2-[(2,2-dimethoxy)ethyl]cyclopentanone
• 英文别名: 2-(2,2-Dimethoxyethyl)cyclopentan-1-one
• CAS: 114389-86-5
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: SKXURCZNFCGRPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,2-二甲氧基乙基)环戊烷-1-酮 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Stereocontrolled construction of carbocyclic rings by sequential cationic cyclization-pinacol rearrangements

  摘要：

  DOI：

  10.1021/ja00186a065
• 作为产物：
  描述：

  2-溴-1,1-二甲氧基乙烷 、 环戊酮 生成 2-(2,2-二甲氧基乙基)环戊烷-1-酮
  参考文献：
  名称：

  Stereocontrolled construction of carbocyclic rings by sequential cationic cyclization-pinacol rearrangements

  摘要：

  DOI：

  10.1021/ja00186a065

文献信息

• Synthesis of 1,4-dicarbonyl compounds by the ceric ammonium nitrate promoted reaction of ketones with vinyl and isopropenyl acetate
  作者：Enrico Baciocchi、Giampiero Civitarese、Renzo Ruzziconi

  DOI：10.1016/s0040-4039(00)96729-7

  日期：1987.1

  1,4-diketones and 4-ketoaldehydes dimethylacetals can be prepared in good yields (65%–82%) by the cerium(IV) ammonium nitrate promoted reaction of ketones with isopropenyl acetate and vinyl acetate, respectively.

  通过硝酸铈（IV）铵铵促进的酮与乙酸异丙烯酯和乙酸乙烯酯的反应，可以高收率（65％–82％）制备1,4-二酮和4-酮醛二甲基乙缩醛。
• Development of the Intramolecular Prins Cyclization/Schmidt Reaction for the Construction of the Azaspiro[4,4]nonane: Application to the Formal Synthesis of (±)-Stemonamine
  作者：Zhi-Hua Chen、Yong-Qiang Tu、Shu-Yu Zhang、Fu-Min Zhang

  DOI：10.1021/ol102955e

  日期：2011.2.18

  A TiCl4-promoted tandem intramolecular Prins cyclization/Schmidt reaction has been designed and developed to be an efficient method for the construction of the azaspiro[4,4]nonane. The present tandem protocol has been employed to construct the tricyclic azaquaternary skeleton (ring A, B, and C) of stemonamine.

  设计并开发了TiCl 4促进的串联分子内Prins环化/施密特反应，作为构建氮杂螺[4,4]壬烷的有效方法。本发明的串联方案已被用于构建三聚氰胺的三环氮杂季铵骨架（环A，B和C）。
• Hydrazulene Ring Systems via Heteroatom-Assisted [1,2]-Shift of Oxonium and Sulfonium Ylides
  作者：Graham K. Murphy、F. G. West

  DOI：10.1021/ol050396p

  日期：2005.4.1

  side chains undergo rearrangement to ether-bridged cycloheptane ring systems on treatment with Cu(hfacac)(2). Stevens [1,2]-shift of an oxonium ylide furnishes the major product (7), in some cases accompanied by minor amounts of a product (8) resulting from [1,2]-shift of a sulfonium ylide. In the subsequent sulfur-triggered cleavage of the bridging ether, the desired bicyclo[5.3.0]heptene was obtained

  [反应：见正文]用Cu（hfacac）（2）处理后，带有重氮酮侧链侧链的环状混合缩醛会发生重排，形成醚桥连的环庚烷环系统。s叶立德的史蒂文斯[1,2]位移提供了主要产物（7），在某些情况下还伴随着from叶立德[1,2]转变产生的少量产物（8）。在随后的桥连醚的硫引发裂解中，获得了所需的双环[5.3.0]庚烯，以及对所得烯丙基缩酮的新型S（N）2'攻击产物。
• Polycyclic oxonium ylides — Use of cyclic acetals as convenient scaffolds in the construction of fused bicyclic compounds containing a medium ring
  作者：Graham K Murphy、Fredrik P Marmsäter、F G West

  DOI：10.1139/v06-111

  日期：2006.10.1

  Cyclic mixed acetals with pendant diazoketone side chains undergo efficient rearrangement to ether-bridged cyclooctanoid and cycloheptanoid systems upon treatment with Cu(hfacac)2. Stevens [1,2]-sh...

  带有悬垂重氮酮侧链的环状混合缩醛在用 Cu(hfacac)2 处理后有效地重排为醚桥连的环辛烷和环庚烷系统。史蒂文斯 [1,2]-sh...
• Total Synthesis of (+)-Sieboldine A: Evolution of a Pinacol-Terminated Cyclization Strategy
  作者：Stephen M. Canham、David J. France、Larry E. Overman

  DOI：10.1021/jo300872y

  日期：2013.1.4

  This article describes synthetic studies that culminated in the first total synthesis of the Lycopodium alkaloid sieboldine A. During this study, a number of pinacol-terminated cationic cyclizations were examined to form the cis-hydrindanone core of sieboldine A. Of these, a mild Au(I)-promoted 1,6-enyne cyclization that was terminated by a semipinacol rearrangement proved to be most efficient. Fashioning the unprecedented N-hydroxyazacyclononane ring embedded within the bicyclo[5.2.1]decane-N,O-acetal moiety of sieboldine A was a formidable challenge. Ultimately, the enantioselective total synthesis of (+)-sieboldine A was completed by forming this ring in good yield by cyclization of a protected-hydroxylamine thioglycoside precursor.