3-(3-Methyl-1-propen-3-yl)cyclopentanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-Methyl-1-propen-3-yl)cyclopentanone
• 英文别名: (3R)-3-(but-3-en-2-yl)cyclopentan-1-one；3-but-3-en-2-ylcyclopentan-1-one
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: XEUGJZRXZIGDEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-环戊烯酮 、 1-氯-2-丁烯 生成 ((E)-3-But-2-enyl)-cyclopentanone 、 3-(3-Methyl-1-propen-3-yl)cyclopentanone
  参考文献：
  名称：

  Conjugate Addition Reactions of Allylic Copper Species Derived from Grignard Reagents: Synthetic and Spectroscopic Aspects

  摘要：

  A general study on the 1,4-addition chemistry of allyl, methallyl, crotyl, and prenyl Grignard-derived organocopper reagents has been conducted. While diallylic cuprates formed from such species are not effective Michael donors, the 1:1:1 combination of an allylic Grignard, CuBr.SMe(2), and Me(3)SiCl leads to high yields of 1,4-adducts. The stereo- and regiochemistry associated with the allylic ligand, where appropriate, has also been examined. Low temperature C-13 NMR studies provide insight as to the nature of these complexes.

  DOI：

  10.1021/jo00103a042

文献信息

• PAN, LI-RUI;TOKOROYAMA, TAKASHI, CHEM. LETT.,(1990) N1, C. 1999-2002
  作者：PAN, LI-RUI、TOKOROYAMA, TAKASHI

  DOI：——

  日期：——
• Conjugate Addition Reactions of Allylic Copper Species Derived from Grignard Reagents: Synthetic and Spectroscopic Aspects
  作者：Bruce H. Lipshutz、Claus Hackmann

  DOI：10.1021/jo00103a042

  日期：1994.12

  A general study on the 1,4-addition chemistry of allyl, methallyl, crotyl, and prenyl Grignard-derived organocopper reagents has been conducted. While diallylic cuprates formed from such species are not effective Michael donors, the 1:1:1 combination of an allylic Grignard, CuBr.SMe(2), and Me(3)SiCl leads to high yields of 1,4-adducts. The stereo- and regiochemistry associated with the allylic ligand, where appropriate, has also been examined. Low temperature C-13 NMR studies provide insight as to the nature of these complexes.