r-4-cyclohexyl-t-3,4-dimethyloxetan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: r-4-cyclohexyl-t-3,4-dimethyloxetan-2-one
• 英文别名: 4-cyclohexyl-3,4-dimethyloxetan-2-one；(3R,4R)-4-cyclohexyl-3,4-dimethyloxetan-2-one
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: GLAKRRNZCZGMOZ-KWQFWETISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  r-4-cyclohexyl-t-3,4-dimethyloxetan-2-one 在 silica gel 作用下， 以95%的产率得到(E)-2-cyclohexyl-2-butene
  参考文献：
  名称：

  A practical and efficient method for the synthesis of .beta.-lactones

  摘要：

  This paper describes a convenient one-step preparation of beta-lactones based on the addition of thiol ester enolates to carbonyl compounds. Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce beta-lactones in good to excellent yield. The new beta-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns. In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded beta-lactone diastereomers, and in some cases the reaction proceeds with excellent stereoselectivity. In conjunction with the stereospecific decarboxylation of beta-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.

  DOI：

  10.1021/jo00003a047
• 作为产物：
  描述：

  硫基丙酸苯酯 、 乙酰基环己烷 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.62h， 以75%的产率得到r-4-cyclohexyl-t-3,4-dimethyloxetan-2-one
  参考文献：
  名称：

  SYNTHESIS OF b-LACTONES AND ALKENES VIA THIOL ESTERS: (E)-2,3-DIMETHYL-3-DODECENE

  摘要：

  DOI：

  10.15227/orgsyn.073.0061

文献信息

• Synthesis of allenes via thermal cycloreversion of .alpha.-alkylidene-.beta.-lactones
  作者：Rick L. Danheiser、Yong Mi Choi、Maria Menichincheri、Eric J. Stoner

  DOI：10.1021/jo00054a011

  日期：1993.1

  This paper describes the application of the solution-phase [2 + 2] cycloreversion of alpha-alkylidene-beta-lactones as a practical method for the generation of substituted allenes. Upon heating in dimethylformamide solution at 110-125-degrees-C, these unsaturated beta-lactone derivatives undergo decarboxylation to provide allenes in good to excellent yield. Alpha-alkylidene-beta-lactones are conveniently prepared via the phenylselenylation of beta-lactone enolates followed by oxidative elimination of the resulting alpha-phenylseleno derivatives. The beta-lactone starting materials are synthesized by the addition of thiol ester enolates to ketones and aldehydes according to our recently reported procedure.
• Inhibition of fatty acid synthase by beta-lactones and other compounds for inhibition of cellular proliferation
  申请人：——

  公开号：US20040024050A1

  公开（公告）日：2004-02-05

  The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis.
• [EN] INHIBITION OF FATTY ACID SYNTHASE BY BETA-LACTONES AND OTHER COMPOUNDS FOR INHIBITION OF CELLULAR PROLIFERATION<br/>[FR] INHIBITION DE SYNTHASE D'ACIDE GRAS PAR BETA-LACTONES ET PAR D'AUTRES COMPOSES DESTINES A INHIBER LA PROLIFERATION CELLULAIRE
  申请人：BURNHAM INST

  公开号：WO2003088975A1

  公开（公告）日：2003-10-30

  The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis.
• A practical and efficient method for the synthesis of .beta.-lactones
  作者：Rick L. Danheiser、James S. Nowick

  DOI：10.1021/jo00003a047

  日期：1991.2

  This paper describes a convenient one-step preparation of beta-lactones based on the addition of thiol ester enolates to carbonyl compounds. Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce beta-lactones in good to excellent yield. The new beta-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns. In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded beta-lactone diastereomers, and in some cases the reaction proceeds with excellent stereoselectivity. In conjunction with the stereospecific decarboxylation of beta-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.
• SYNTHESIS OF b-LACTONES AND ALKENES VIA THIOL ESTERS: (E)-2,3-DIMETHYL-3-DODECENE
  作者：Danheiser, Rick L.、Nowick, James S.、Lee, Janette H.、Miller, Raymond F.、Huboux, Alexandre H.、Mathre, David J.、Shinkai, Ichiro

  DOI：10.15227/orgsyn.073.0061

  日期：——