3-(2-Methyl-2-buten-4-yl)cyclohexanone | 29843-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-Methyl-2-buten-4-yl)cyclohexanone
• 英文别名: 3-(2-methyl-2-buten-4-yl)cyclohexane；3-(3-methyl-2-butenyl)cyclohexanone；3-(3-methylbut-2-enyl)cyclohexan-1-one
• CAS: 29843-83-2
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: WVQCNPBJZDPCBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  244.4±9.0 °C(Predicted)
• 密度：
  0.906±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-Methyl-2-buten-4-yl)cyclohexanone 在 palladium on activated charcoal 氢气 作用下， 生成 3-(3-Methylbutyl)cyclohexan-1-one
  参考文献：
  名称：

  Descoins,C.; Julia,M., Bulletin de la Societe Chimique de France, 1970, p. 1816 - 1822

  摘要：

  DOI：
• 作为产物：
  描述：

  2-环己烯-1-酮 生成 3-(2-Methyl-2-buten-4-yl)cyclohexanone
  参考文献：
  名称：

  LIPSHUTZ, BRUCE H.;ELLSWORTH, EDMUND L.;DIMOCK, STUART H.;SMITH, ROBIN A.+, J. AMER. CHEM. SOC., 112,(1990) N1, C. 4404-4410

  摘要：

  DOI：

文献信息

• Direct formation of highly functionalized allylic organocopper reagents from allylic chlorides and acetates
  作者：Douglas E. Stack、Bryan T. Dawson、Reuben D. Rieke

  DOI：10.1021/ja00039a023

  日期：1992.6

  The direct formation of highly functionalized allylic organocopper reagents has been carried out using a highly active form of zerovalent copper (Cu*). The cold-temperature reduction of CuCN.nLiX complexes by lithium naphthalenide in THF under an argon atmosphere produces the Cu* complex, which reacts rapidly with primary and secondary allyl chlorides at −100°C with little homocoupling. Allyl, methallyl

  使用高活性形式的零价铜 (Cu*) 直接形成高度官能化的烯丙基有机铜试剂。在氩气气氛下，萘化锂在 THF 中低温还原 CuCN.nLiX 络合物产生 Cu* 络合物，该络合物在 -100°C 下与伯和仲烯丙基氯快速反应，几乎没有均偶联。烯丙基、甲基烯丙基和巴豆基乙酸酯也在低温下与 Cu* 氧化加成以提供相应的有机铜试剂。值得注意的是，烯丙基氯可包含多种官能团，包括酮、α,β-不饱和酮、环氧化物、乙酸烷基酯、酯、烷基氯、腈和氨基甲酸酯
• Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds
  作者：Akira Yanagisawa、Shigeki Habaue、Katsutaka Yasue、Hisashi Yamamoto

  DOI：10.1021/ja00093a010

  日期：1994.7

  The first direct preparation of allylbarium reagents by reaction of insitu generated reactive barium with various allylic chlorides and their new and unexpected selective allylation reactions with carbonyl compounds are disclosed. Highly reactive barium was readily prepared by the reduction of barium iodide with 2 equiv of lithium biphenylide in dry THF at room temperature. A variety of carbonyl compounds reacted with barium reagents generated from (E)- or (Z)-allylic chlorides in THF at -78 degrees C. All reactions resulted in high yields with remarkable alpha-selectivities not only with aldehydes but also with ketones. The double bond geometry of the starting allylic chloride was completely retained in each case. Stereochemically homogeneous (E)- and (Z)beta,gamma-unsaturated carboxylic acids were easily prepared in good yields by highly alpha-selective carboxylation of allylic barium reagents with carbon dioxide. A selective Michael addition reaction with alpha,beta-unsaturated cycloalkanone was also achieved using an allylbarium reagent. Treatment of 2-cyclopentenone (1 equiv) with allylbarium chloride (2 equiv) in THF at -78 degrees C for 20 min afforded 3-allylcyclopentanone in 94% yield with a 1,4/1,2 ratio of >99/1. Furthermore, the in situ generated barium enolate was efficiently trapped with various kinds of electrophiles (Me(2)C=CHCH2Br, (C5H11CHO)-C-n, and CH3COCl).
• Lipshutz, Bruce H.; Ellsworth, Edmund L.; Dimock, Stuart H., Journal of the American Chemical Society, 1990, vol. 112, # 11, p. 4404 - 4410
  作者：Lipshutz, Bruce H.、Ellsworth, Edmund L.、Dimock, Stuart H.、Smith, Robin A.J.

  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.
• LIPSHUTZ, BRUCE H.;ELLSWORTH, EDMUND L.;DIMOCK, STUART H.;SMITH, ROBIN A.+, J. AMER. CHEM. SOC., 112,(1990) N1, C. 4404-4410
  作者：LIPSHUTZ, BRUCE H.、ELLSWORTH, EDMUND L.、DIMOCK, STUART H.、SMITH, ROBIN A.+

  DOI：——

  日期：——