(+/-)-4-tert-Butyl-3,3-dimethyl-2-oxetanone | 74687-05-1

• 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: (+/-)-4-tert-Butyl-3,3-dimethyl-2-oxetanone
• 英文别名: 4-tert-butyl-3,3-dimethyl-2-oxetanone；4-tert-butyl-3,3-dimethyloxetan-2-one
• CAS: 74687-05-1
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: VCRBVPKKEJMUOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• 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：

  (+/-)-4-tert-Butyl-3,3-dimethyl-2-oxetanone 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 以50%的产率得到2-tert-Butyl-3,3-dimethyl-4-methylene-oxetane
  参考文献：
  名称：

  A Versatile Preparation of 2-Methyleneoxetanes

  摘要：

  DOI：

  10.1021/jo9611733
• 作为产物：
  描述：

  (3R,4S)-3-methyl-4-tert-butyloxetan-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-4-tert-Butyl-3,3-dimethyl-2-oxetanone
  参考文献：
  名称：

  .alpha. Deprotonation of .beta.-lactones - an example of a forbidden .beta. elimination

  摘要：

  DOI：

  10.1021/ja00530a052

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 .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
• 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.
• 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：——