3-benzoyl-3-phenyloxetan-2-one | 247216-13-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-benzoyl-3-phenyloxetan-2-one
• CAS: 247216-13-3
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: INFIDULQQUIHSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-3-phenyloxetan-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 以20%的产率得到(2-Methylidene-3-phenyloxetan-3-yl)-phenylmethanone
  参考文献：
  名称：

  Preparation and Properties of 2-Methyleneoxetanes

  摘要：

  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.

  DOI：

  10.1021/jo9906072
• 作为产物：
  描述：

  3-[hydroxy(phenyl)methyl]-3-phenyloxetan-2-one 在 pyridinium chlorochromate 作用下， 以20%的产率得到3-benzoyl-3-phenyloxetan-2-one
  参考文献：
  名称：

  Oxoammonium Salts. 6.¹ 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Perchlorate:  A Stable and Convenient Reagent for the Oxidation of Alcohols. Silica Gel Catalysis

  摘要：

  4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate, 1, is a stable, nonhygroscopic oxoammonium salt that is easily prepared and can be used for the oxidation of alcohols to ketones or aldehydes in near quantitative yields. The reaction is colorimetric, does not require anhydrous conditions, does not involve heavy metals, and can be carried out conveniently. Furthermore, the oxidant can be easily regenerated. The oxidation is somewhat specific in that the relative reactivities of an allyl alcohol (geraniol), benzaldehyde, and 1-decanol are about 100: 1:0.1. The reaction is catalyzed by silica gel.

  DOI：

  10.1021/jo981322c

文献信息

• Oxoammonium Salts. 6.¹ 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Perchlorate:  A Stable and Convenient Reagent for the Oxidation of Alcohols. Silica Gel Catalysis
  作者：James M. Bobbitt

  DOI：10.1021/jo981322c

  日期：1998.12.1

  4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate, 1, is a stable, nonhygroscopic oxoammonium salt that is easily prepared and can be used for the oxidation of alcohols to ketones or aldehydes in near quantitative yields. The reaction is colorimetric, does not require anhydrous conditions, does not involve heavy metals, and can be carried out conveniently. Furthermore, the oxidant can be easily regenerated. The oxidation is somewhat specific in that the relative reactivities of an allyl alcohol (geraniol), benzaldehyde, and 1-decanol are about 100: 1:0.1. The reaction is catalyzed by silica gel.
• 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.