(+/-)-3,3-Dimethyl-4-phenyl-2-oxetanone | 35947-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-3,3-Dimethyl-4-phenyl-2-oxetanone
• 英文别名: 2,2-dimethyl-3-phenylpropan-3-olide；3,3-Dimethyl-4-phenyl-2-oxetanone；3,3-dimethyl-4-phenyloxetan-2-one；3,3-dimethyl-4-phenyl-oxetan-2-one；3,3-Dimethyl-4-phenyloxetan-2-on
• CAS: 35947-70-7
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: TXMGTZSPTXLDNX-UHFFFAOYSA-N

物化性质

• 沸点：
  279.2±29.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (+/-)-3,3-Dimethyl-4-phenyl-2-oxetanone 在 四甲基乙二胺 作用下， 以 癸烷 为溶剂， 以100%的产率得到2-甲基-1-苯基丙烯
  参考文献：
  名称：

  Thermolyses of 3-alkyl-4-phenyl-2-oxetanones and related compounds

  摘要：

  DOI：

  10.1021/jo01300a017
• 作为产物：
  描述：

  3-羟基-2,2-二甲基-3-苯基丙酸 在 4-二甲氨基吡啶 、 2-甲基-6-硝基苯甲酸酐 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 以90%的产率得到(+/-)-3,3-Dimethyl-4-phenyl-2-oxetanone
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r

文献信息

• Phosphine-Catalyzed Asymmetric Synthesis of β-Lactones from Disubstituted Ketenes and Aldehydes
  作者：Shi Chen、Mukulesh Mondal、Ahmad A. Ibrahim、Kraig A. Wheeler、Nessan J. Kerrigan

  DOI：10.1021/jo500486e

  日期：2014.6.6

  general catalytic procedure for the formation of β-lactones bearing two stereogenic centers, from disubstituted ketenes and achiral aldehydes. BINAPHANE was found to display excellent enantioselectivity (≥90% ee for eight examples) and good diastereoselectivity (≥90:10 for 13 examples) in catalyzing the formation of β-lactones bearing two stereogenic centers from achiral aldehydes (both aromatic and aliphatic)

  在本文中，我们描述了由双取代的烯酮和非手性醛形成带有两个立体中心的β-内酯的一般催化程序。发现BINAPHANE在催化由非手性醛（芳族和脂族）和两个非手性醛形成带有两个立构中心的β-内酯时，表现出优异的对映选择性（对于8个实例≥90％ee）和良好的非对映选择性（对于13个实例≥90：10）。烷基芳基烯酮或二烷基烯酮。在这些反应中观察到偏好形成反式非对映异构体。对于那些其中BINAPHANE失败作为催化剂的反应，三Ñ发现丁基丁基膦是一种有效的非手性亲核催化剂，在外消旋β-内酯的形成中具有良好的收率和非对映选择性。通过31 P NMR光谱监测反应并与在膦催化的乙烯酮均二聚反应中观察到的先前表征的中间体进行比较，获得了有关烯醇中间体参与反应机理的证据。
• 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
• On the antibiotic activity of oxazolomycin
  作者：Claire L. Bagwell、Mark G. Moloney、Amber L. Thompson

  DOI：10.1016/j.bmcl.2008.05.105

  日期：2008.7

  Structural analysis of oxazolomycin and simpler fragments containing a common 3-hydroxy-2,2-dimethylpropanamide moiety has indicated that a U-shaped conformation is preferred, in some cases stabilised by hydrogen bonding between the N-H and O-H residues, as shown by a combination of molecular modelling, NMR spectroscopic and single crystal X-ray analysis. A direct synthesis of this unit has been established via the opening of b-lactones by a range of amines, and their antibacterial activity been shown to vary with the hydrophobic character of the substituents. (c) 2008 Elsevier Ltd. All rights reserved.
• 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：——
• Thermolyses of 3-alkyl-4-phenyl-2-oxetanones and related compounds
  作者：Toshiro Imai、Shinya Nishida

  DOI：10.1021/jo01300a017

  日期：1980.6