噁丁环,3-甲基-2-亚甲基-3-苯基- | 183245-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 噁丁环,3-甲基-2-亚甲基-3-苯基-
• 英文名称: 3-methyl-2-methylene-3-phenyloxetane
• 英文别名: 3-methyl-3-phenyl-2-methyleneoxetane；3-Methyl-2-methylidene-3-phenyloxetane
• CAS: 183245-70-7
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: DUQIONAZQOQHKI-UHFFFAOYSA-N

物化性质

• 沸点：
  235.7±40.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  噁丁环,3-甲基-2-亚甲基-3-苯基- 在 二甲基二环氧乙烷 作用下， 以100%的产率得到3-methyl-3-phenyl-1,5-dioxaspiro[3.2]hexane
  参考文献：
  名称：

  The First General Synthesis of 1,5-Dioxaspiro[3.2]hexanes

  摘要：

  DOI：

  10.1021/jo981309s
• 作为产物：
  描述：

  DL-托品酸 在 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 生成 噁丁环,3-甲基-2-亚甲基-3-苯基-
  参考文献：
  名称：

  A Versatile Preparation of 2-Methyleneoxetanes

  摘要：

  DOI：

  10.1021/jo9611733

文献信息

• Preparation and reactions of 4-oxaspiro[2.3]hexanes
  作者：Henri Bekolo、Amy R. Howell

  DOI：10.1039/b010095l

  日期：——

  2-Methyleneoxetanes were converted in excellent yields to 4-oxaspiro[2.3]hexanes under modified Simmons–Smith conditions. Treatment of the oxaspirohexanes with BF3·Et2O provided cyclopentanones, cyclobutanones or 4-methylenetetrahydrofurans, depending on the substituents.

  在改良的西蒙斯-史密斯条件下，将2-亚甲基氧杂环丁烷以优异的收率转化为4-氧杂螺[2.3]己烷。提供了用BF 3 ·Et 2 O处理氧杂环己烷的方法环戊酮，环丁酮或4-亚甲基四氢呋喃，具体取决于取代基。
• Pt-Catalyzed Rearrangement of Oxaspirohexanes to 3-Methylenetetrahydrofurans: Scope and Mechanism
  作者：Christian A. Malapit、Sampada M. Chitale、Meena S. Thakur、Rosa Taboada、Amy R. Howell

  DOI：10.1021/acs.joc.5b00604

  日期：2015.5.15

  A novel Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans is reported. Mechanistic studies by 13C-labeling experiments confirm oxidative addition of Pt(II) regioselectively to the least substituted carbon–carbon bond of the cyclopropane to form a platinacyclobutane intermediate. To our knowledge, this is the first alkoxy-substituted platinacyclobutane that has been observed

  报道了新的Pt催化的氧杂螺正己烷重排成3-亚甲基四氢呋喃。通过13 C标记实验进行的机理研究证实，Pt（II）区域选择性地氧化添加到环丙烷的最少取代的碳-碳键上，从而形成铂环丁烷中间体。据我们所知，这是第一个在光谱上观察到的烷氧基取代的铂基环丁烷。描述了这种新的Pt催化转化的范围和提出的机理。
• Ring opening reactions of 2-methyleneoxetanes
  作者：Ying Wang、Henri Bekolo、Amy R. Howell

  DOI：10.1016/s0040-4020(02)00724-x

  日期：2002.8

  Ring opening of 2-methyleneoxetanes with stabilized carbanion nucleophiles provides substituted ketones. The intermediate enolate can be trapped as its silylenol ether. If the 2-methyleneoxetane is exposed to more strongly basic carbanions, the corresponding homopropargylic alcohol is isolated in excellent yield. A variety of heteroatom nucleophiles also open the 2-methyleneoxetane in good to excellent yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.
• An Unanticipated Ring-Opening of 2-Methyleneoxetanes:  A Fundamentally New Approach to the Preparation of Homopropargylic Alcohols
  作者：Lisa M. Dollinger、Amy R. Howell

  DOI：10.1021/jo9816360

  日期：1998.10.1