(+/-)-3-Isopropyl-1-oxaspiro<3.5>nonan-2-one | 131436-02-7

• 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: (+/-)-3-Isopropyl-1-oxaspiro<3.5>nonan-2-one
• 英文别名: 3-isopropyl-1-oxaspiro<3.5>nonan-2-one；3-isopropyloxetan-2-one-4-spirocyclohexane；3-Propan-2-yl-1-oxaspiro[3.5]nonan-2-one
• CAS: 131436-02-7
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: LXYHUSGTQHTZPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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

• 作为产物：
  描述：

  2-溴-3-甲基丁酰溴 在 indium(III) chloride 、 硫酸 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 (+/-)-3-Isopropyl-1-oxaspiro<3.5>nonan-2-one
  参考文献：
  名称：

  通过羰基化合物，α-溴代链烷酸酯和铟的Reformatsky反应合成取代的β-内酯

  摘要：

  二，三和四取代的β-内酯可通过一个步骤在牺牲铟阳极上通过Reformatsky反应使苯基α-溴链烷酸酯与酮或醛发生反应。用铟粉可获得可比的结果。如果使用锌代替铟，则β-内酯的收率会大大降低。

  DOI：

  10.1016/0040-4020(95)00039-b

文献信息

• Synthesis of .beta.-Lactones via a Spontaneous Intramolecular Cyclization of O-Lithiated Phenyl .beta.-Hydroxyalkanoates Obtained by Aldolization of Ketones or Aldehydes with Lithium Enolates of Phenyl Esters
  作者：Christine Wedler、Annamarie Kunath、Hans Schick

  DOI：10.1021/jo00108a052

  日期：1995.2
• 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.
• DANHEISER, RICK L.;NOWICK, JAMES S., J. ORG. CHEM., 56,(1991) N, C. 1176-1185
  作者：DANHEISER, RICK L.、NOWICK, JAMES S.

  DOI：——

  日期：——
• Wedler Christine, Kunath Annamarie, Schick Hans, J. Org. Chem, 60 (1995) N 3, S 758-760
  作者：Wedler Christine, Kunath Annamarie, Schick Hans

  DOI：——

  日期：——
• Synthesis of substituted β-lactones by a Reformatsky reaction of carbonyl compounds, phenyl α-bromoalkanoates, and indium
  作者：Hans Schick、Ralf Ludwig、Katharina Kleiner、Annamarie Kunath

  DOI：10.1016/0040-4020(95)00039-b

  日期：1995.3

  Di-, tri-, and tetrasubstituted β-lactones are accessible in a one-step procedure by a Reformatsky reaction of phenyl α-bromoalkanoates with ketones or aldehydes at a sacrificial indium anode. With indium powder comparable results are obtained. The yield of β-lactones is significantly lower, if zinc is used instead of indium.

  二，三和四取代的β-内酯可通过一个步骤在牺牲铟阳极上通过Reformatsky反应使苯基α-溴链烷酸酯与酮或醛发生反应。用铟粉可获得可比的结果。如果使用锌代替铟，则β-内酯的收率会大大降低。