3-dimethylmethylene-5-isopropyl-2-furanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-dimethylmethylene-5-isopropyl-2-furanone
• 英文别名: 5-Isopropyl-3-(propan-2-ylidene)furan-2(3H)-one；5-propan-2-yl-3-propan-2-ylidenefuran-2-one
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: SSWXCJGZXHUGMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-甲基-1-丁烯-3-炔 、 alkaline earth salt of/the/ methylsulfuric acid 在 亚磷酸三苯酯 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 Rh(1+)(1,5-cyclooctadiene)(η6-C6H5B(1-)Ph3) 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 50.0~70.0 ℃ 、2.13 MPa 条件下， 反应 54.0h， 生成 3-dimethylmethylene-5-isopropyl-2-furanone
  参考文献：
  名称：

  Chemo- and Regioselective Cyclohydrocarbonylation of α-Keto Alkynes Catalyzed by a Zwitterionic Rhodium Complex and Triphenyl Phosphite

  摘要：

  alpha-Keto alkynes react with CO and H-2 in the presence of catalytic quantities of the zwitterionic rhodium complex (eta(6)-C6H5BPh3)Rh--(+)(1,5-COD) and triphenyl phosphite affording either the 2-, 2(3H)-, or 2(5H)-furanones in 61-93% yields. The cyclohydrocarbonylation is readily accomplished using substrates containing alkyl, aryl, vinyl, and alkoxy groups at the acetylenic terminal, as well as a variety of primary, secondary, and tertiary alkyl, aryl, and heteroaryl groups connected to the ketone functionality. Structural and electronic properties present in the starting materials mediate the chemo- and regioselectivity of the reaction.

  DOI：

  10.1021/jo000230w

文献信息

• Chemo- and Regioselective Cyclohydrocarbonylation of α-Keto Alkynes Catalyzed by a Zwitterionic Rhodium Complex and Triphenyl Phosphite
  作者：Bernard G. Van den Hoven、Bassam El Ali、Howard Alper

  DOI：10.1021/jo000230w

  日期：2000.6.1

  alpha-Keto alkynes react with CO and H-2 in the presence of catalytic quantities of the zwitterionic rhodium complex (eta(6)-C6H5BPh3)Rh--(+)(1,5-COD) and triphenyl phosphite affording either the 2-, 2(3H)-, or 2(5H)-furanones in 61-93% yields. The cyclohydrocarbonylation is readily accomplished using substrates containing alkyl, aryl, vinyl, and alkoxy groups at the acetylenic terminal, as well as a variety of primary, secondary, and tertiary alkyl, aryl, and heteroaryl groups connected to the ketone functionality. Structural and electronic properties present in the starting materials mediate the chemo- and regioselectivity of the reaction.