1-Cyclopropyl-3-(phenylthio)-1-propanone | 137518-34-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-Cyclopropyl-3-(phenylthio)-1-propanone
• 英文别名: 1-Cyclopropyl-3-phenylsulfanylpropan-1-one
• CAS: 137518-34-4
• 化学式: C₁₂H₁₄OS
• 分子量: 206.309
• InChiKey: TVFNLVAWFIBHIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-trimethylsilyloxy-1,1'-bicyclopropyl 、 苯硫酚 生成 1-Cyclopropyl-3-(phenylthio)-1-propanone
  参考文献：
  名称：

  .beta.-Trichlorostannyl ketones and aldehydes. Preparation and facile amine-induced dehydrostannation leading to .alpha.-methylene ketones and aldehydes

  摘要：

  Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give beta-trichlorostannyl ketones and aldehydes 3 in high yields. The beta-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding alpha-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N',N'-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to alpha-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The H-1 NMR, C-13 NMR, Sn-119 NMR, and IR spectral properties of beta-stannyl ketones and aldehydes are also reported.

  DOI：

  10.1021/jo00027a008

文献信息

• .beta.-Trichlorostannyl ketones and aldehydes. Preparation and facile amine-induced dehydrostannation leading to .alpha.-methylene ketones and aldehydes
  作者：Hiroyuki Nakahira、Ilhyong Ryu、Masanobu Ikebe、Yoshiaki Oku、Akiya Ogawa、Nobuaki Kambe、Noboru Sonoda、Shinji Murai

  DOI：10.1021/jo00027a008

  日期：1992.1

  Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give beta-trichlorostannyl ketones and aldehydes 3 in high yields. The beta-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding alpha-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N',N'-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to alpha-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The H-1 NMR, C-13 NMR, Sn-119 NMR, and IR spectral properties of beta-stannyl ketones and aldehydes are also reported.