3-allyl-2-methylene-3-phenyloxetane | 183245-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-allyl-2-methylene-3-phenyloxetane
• 英文别名: 2-Methylidene-3-phenyl-3-prop-2-enyloxetane
• CAS: 183245-71-8
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: JHALSUQEWFHXOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  3-allyl-2-methylene-3-phenyloxetane 在 二甲基二环氧乙烷 作用下， 以97%的产率得到3-allyl-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 3-allyl-2-methylene-3-phenyloxetane
  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。
• 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