3-methyl-1-oxaspiro<3.5>nonan-2-one | 121821-93-0

• 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-methyl-1-oxaspiro<3.5>nonan-2-one
• 英文别名: 3-methyloxetan-2-one-4-spirocyclohexane；3-methyl-4-spirocyclohexyloxetan-2-one；3-Methyl-1-oxaspiro[3.5]nonan-2-one
• CAS: 121821-93-0
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: FQNMNDSTIIXLQA-UHFFFAOYSA-N

物化性质

• 熔点：
  25 °C
• 沸点：
  50 °C(Press: 0.03 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  3-methyl-1-oxaspiro<3.5>nonan-2-one 在 silica gel 作用下， 以90%的产率得到亚乙基环己烷
  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：

  2-(1'-hydroxycyclohexyl)propionic acid 在 苯磺酰氯 作用下， 以 吡啶 为溶剂， 以96%的产率得到3-methyl-1-oxaspiro<3.5>nonan-2-one
  参考文献：
  名称：

  An efficient, highly regioselective synthesis of substituted (1-cyclohexenyl) acetic acid derivatives via ionization/elimination of β-lactones

  摘要：

  DOI：

  10.1016/s0040-4039(00)95245-6

文献信息

• 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。
• 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.
• 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：——
• An efficient, highly regioselective synthesis of substituted (1-cyclohexenyl) acetic acid derivatives via ionization/elimination of β-lactones
  作者：T.Howard Black、Stephen L Maluleka

  DOI：10.1016/s0040-4039(00)95245-6

  日期：1989.1
• Preparation and Properties of 2-Methyleneoxetanes
  作者：Lisa M. Dollinger、Albert J. Ndakala、Mehrnoosh Hashemzadeh、Gan Wang、Ying Wang、Isamir Martinez、Joel T. Arcari、David J. Galluzzo、Amy R. Howell、Arnold L. Rheingold、Joshua S. Figuero

  DOI：10.1021/jo9906072

  日期：1999.9.1

  The methylenation of beta-lactones 5 with dimethyltitanocene provides a versatile, reliable, and highly chemoselective entry to 2-methyleneoxetanes 7. The conversion proceeds selectively in the presence of alkenes, unprotected alcohols, and a variety of other carbonyl moieties, A study of conditions for the optimization of this reaction is delineated. In addition, the first X-ray structure of a 2-methyleneoxetane, which shows its similarity to related p-lactones, is reported. Reactivity studies of 2-methyleneoxetanes are presented in which it is demonstrated that these compounds are attacked at C-4 with a nucleophile; then, subsequently, the resultant enolate reacted with an electrophile. An interesting dichotomy of reactivity was observed when methyleneoxetane 7c was treated with electrophiles. Reaction of 7c with acetic acid gave acetoxyoxetane 19. When 7c was exposed to bromine, dibromoketone 20 resulted.