Methyl 2,2-dimethyl-3-phenyl-3-oxiranecarboxylate | 76527-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: Methyl 2,2-dimethyl-3-phenyl-3-oxiranecarboxylate
• 英文别名: Methyl 3,3-dimethyl-2-phenyloxirane-2-carboxylate
• CAS: 76527-29-2
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: LVMYNDJSYMWEGM-UHFFFAOYSA-N

物化性质

• 沸点：
  261.6±28.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Methyl 2,2-dimethyl-3-phenyl-3-oxiranecarboximidate 在 盐酸 作用下， 以 乙醚 为溶剂， 以55%的产率得到Methyl 2,2-dimethyl-3-phenyl-3-oxiranecarboxylate
  参考文献：
  名称：

  Electrolytic oxidation of ketones in a methanolic solution of sodium cyanide in the presence of catalytic amounts of potassium iodide

  摘要：

  The indirect electrolytic oxidation of ketones (1) in methanolic sodium cyanide was studied using iodide ion as a mediator. The product and the reactivity of ketone were dependent on the nature of the alkyl groups attached to the carbonyl group. Thus, 2-alkyl and 2,2-dialkyl ketones afforded the corresponding oxiranecarbonitriles 2 along with small amounts of methyl oxiranecarboximidate 3, whereas acetophenones exclusively yielded benzoylpropanedinitriles 4.

  DOI：

  10.1021/jo00075a010

文献信息

• Photochemical Wittig reaction of quasi-phosphonium ylides
  作者：Hideo Tomioka、Naoki Ichikawa、Hideki Murata

  DOI：10.1039/c39920000193

  日期：——

  α-(Methoxycarbonyl)benzylidene quasi-phosphonium ylides, which are unreactive toward most carbonyl compounds, are found to undergo the Wittig reaction upon irradiation; irradiation with acyclic carbonyl compounds, e.g. benzaldehydes and acetophenones, afford the corresponding alkenes, whereas the reaction with cyclohexanone affords 1-phenyl-1-(methoxycarbonyl)hepta-1, 2-diene.

  α-(甲氧羰基)苄叉次膦叶立德对大多数羰基化合物不反应，但在光照下可进行Wittig反应；无环羰基化合物（如苯甲醛和苯乙酮）的光照反应得到相应的烯烃，而环己酮的反应得到1-苯基-1-(甲氧羰基)庚-1,2-二烯。
• Synthesis of α,β-epoxy diazomethyl ketones
  作者：L. Thijs、F.L.M. Smeets、P.J.M. Cillissen、J. Harmsen、B. Zwanenburg

  DOI：10.1016/0040-4020(80)80105-0

  日期：1980.1

  The preparation of eighteen epoxy diazomethyl ketones 1 is described. Two general methods were developed. Firstly, treatment of the mixed anhydrides of glycidic acids and carbonic acid ester with diazomethane led to the title compounds in yields ranging from 17–74%. Secondly, glycidyl chlorides which were obtained from sodium glycidates and oxalyl chloride, gave the desired products upon treatment

  描述了十八种环氧重氮甲基酮1的制备。开发了两种通用方法。首先，用重氮甲烷处理缩水甘油酸和碳酸酯的混合酸酐会导致标题化合物的收率在17-74％之间。其次，由缩水甘油酸钠和草酰氯制得的缩水甘油氯经重氮甲烷处理后可提供所需的产物（收率60-74％）。所需的α，β-环氧羧酸酯是通过Darzens缩合和α，β-不饱和酯的环氧化制备的，但在某些情况下还可以通过α-氧代羧酸酯与重氮甲烷的反应制得。
• Method for isomerization a glycidate derivative
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0153692B1

  公开（公告）日：1992-07-29
• US4621150A
  申请人：——

  公开号：US4621150A

  公开（公告）日：1986-11-04
• Electrolytic oxidation of ketones in a methanolic solution of sodium cyanide in the presence of catalytic amounts of potassium iodide
  作者：Mitsuhiro Okimoto、Toshiro Chiba

  DOI：10.1021/jo00075a010

  日期：1993.11

  The indirect electrolytic oxidation of ketones (1) in methanolic sodium cyanide was studied using iodide ion as a mediator. The product and the reactivity of ketone were dependent on the nature of the alkyl groups attached to the carbonyl group. Thus, 2-alkyl and 2,2-dialkyl ketones afforded the corresponding oxiranecarbonitriles 2 along with small amounts of methyl oxiranecarboximidate 3, whereas acetophenones exclusively yielded benzoylpropanedinitriles 4.