5,5-dimethyl-3-methylene-4-phenyldihydrofuran-2(3H)-one | 63506-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5,5-dimethyl-3-methylene-4-phenyldihydrofuran-2(3H)-one
• 英文别名: 5,5-Dimethyl-3-methylidene-4-phenyloxolan-2-one
• CAS: 63506-92-3
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: SYKAFLOVDXCZNR-UHFFFAOYSA-N

物化性质

• 熔点：
  93-94 °C(Solv: ethanol (64-17-5))
• 沸点：
  339.6±41.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 二氯乙基铝 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 5,5-dimethyl-3-methylene-4-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  应变驱动的各向异性重排：α-亚甲基-γ-丁内酯的统一环扩环方法

  摘要：

  已经实现了前所未有的应变驱动的α-亚甲基-β-内酯的重整排列，这使得能够有效利用显示出显着结构多样性的各种α-亚甲基-γ-丁内酯。该反应的几个吸引人的特征，包括出色的效率，高立体特异性，可预测的化学选择性和广泛的底物范围，使其成为合成天然或合成来源的含MBL分子的有力工具。实验和计算证据均表明，致各向异性重排的新变体以二元模式进行：虽然异步协同机制最有可能解释了以氢迁移为特征的反应，但在芳基迁移的情况下，涉及involving离子中间体的逐步过程是有利的。

  DOI：

  10.1002/anie.202013169

文献信息

• A One-Pot C–H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones
  作者：Matthew G. Lloyd、Richard J. K. Taylor、William P. Unsworth

  DOI：10.1021/ol501092m

  日期：2014.5.16

  A one-pot C-H insertion/olefination sequence for the conversion of alpha-diazo-alpha-(dialkoxyphosphoryl)acetates into alpha-alkylidene-gamma-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.
• α-Alkylidene-γ-butyrolactone synthesis via one-pot C–H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B
  作者：Matthew G. Lloyd、Mariantonietta D'Acunto、Richard J.K. Taylor、William P. Unsworth

  DOI：10.1016/j.tet.2014.09.054

  日期：2015.9

  A system for the synthesis of alpha-alkylidene-gamma-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of alpha-diazoa-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (+/-)-cedarmycins A and B is also described. (C) 2014 Elsevier Ltd. All rights reserved.
• Carlson, Robert M.; DeLane, James C.; Liu, Tian-lin, Synthetic Communications, 1985, vol. 15, # 7, p. 657 - 662
  作者：Carlson, Robert M.、DeLane, James C.、Liu, Tian-lin

  DOI：——

  日期：——
• LAMBERT, FRANCOIS;KIRSCHLEGER, BERNARD;VILLIERAS, JEAN, J. ORGANOMET. CHEM., 406,(1991) N-2, C. 71-86
  作者：LAMBERT, FRANCOIS、KIRSCHLEGER, BERNARD、VILLIERAS, JEAN

  DOI：——

  日期：——
• CARLSON, R. M.;DELANE, J. C.;TIAN-LIN, LIU, SYNTH. COMMUN., 1985, 15, N 7, 657-662
  作者：CARLSON, R. M.、DELANE, J. C.、TIAN-LIN, LIU

  DOI：——

  日期：——