4-cyclopropyl-5-methylene-1,3-dioxolan-2-one | 1138342-44-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 4-cyclopropyl-5-methylene-1,3-dioxolan-2-one
• 英文别名: 4-Cyclopropyl-5-methylidene-1,3-dioxolan-2-one；4-cyclopropyl-5-methylidene-1,3-dioxolan-2-one
• CAS: 1138342-44-5
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: MHSPVDDJHZQKJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl 1-cyclopropylprop-2-yn-1-yl carbonate 在 [(MeCN)Ph₃PAu]SbF₆ 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以49%的产率得到4-cyclopropyl-5-methylene-1,3-dioxolan-2-one
  参考文献：
  名称：

  Gold-catalyzed rearrangement of propargylic tert-butyl carbonates

  摘要：

  Diversely substituted 4-alkylidene-1,3-dioxolan-2-ones are efficiently synthesized by a gold(I)-catalyzed rearrangement of propargylic tert-butyl carbonates. The substrates are readily accessible and the transformation, which is performed under mild reaction conditions using a low loading of catalyst, allows the synthesis of cyclic carbonates, which would be less efficiently obtained using traditional methods. This procedure has also been applied to the stereoselective synthesis of (E)- or (Z)-4-halomethylene-1,3-dioxolan-2-ones, which Proved to be suitable substrates for palladium-catalyzed cross-coupling reactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.108

文献信息

• Gold-catalyzed rearrangement of propargylic tert-butyl carbonates
  作者：Andrea K. Buzas、Florin M. Istrate、Fabien Gagosz

  DOI：10.1016/j.tet.2008.11.108

  日期：2009.2

  Diversely substituted 4-alkylidene-1,3-dioxolan-2-ones are efficiently synthesized by a gold(I)-catalyzed rearrangement of propargylic tert-butyl carbonates. The substrates are readily accessible and the transformation, which is performed under mild reaction conditions using a low loading of catalyst, allows the synthesis of cyclic carbonates, which would be less efficiently obtained using traditional methods. This procedure has also been applied to the stereoselective synthesis of (E)- or (Z)-4-halomethylene-1,3-dioxolan-2-ones, which Proved to be suitable substrates for palladium-catalyzed cross-coupling reactions. (C) 2008 Elsevier Ltd. All rights reserved.