3-(6-chlorohexyl)cyclohexanone | 110718-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(6-chlorohexyl)cyclohexanone
• 英文别名: 3-(6-chlorohexyl)cyclohexan-1-one
• CAS: 110718-81-5
• 化学式: C₁₂H₂₁ClO
• 分子量: 216.751
• InChiKey: HXBDBMYOSJJOJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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-环己烯-1-酮 、 1-溴-6-氯己烷 在 CuI*P(n-Bu)3 、 三丁基膦 、 lithium dihydronaphthylide radical 作用下， 生成 3-(6-chlorohexyl)cyclohexanone
  参考文献：
  名称：

  利用高反应性铜制备的新型有机铜试剂

  摘要：

  通过碘化亚铜（I）/三烷基膦配合物的萘锂制备了高反应性的铜溶液。这些活化的铜溶液将在非常温和的条件下与有机卤化物反应，形成稳定的有机铜试剂。重要的是，有机铜试剂可以包含大量的官能团，例如酯，腈，氯，环氧基和酮基。这些官能化的有机铜物质经历许多其他有机铜物质典型的反应。已经成功实现了分子间的1,4-加成，环氧化物开放反应以及与酰氯的酮形成。另外，该方法已经应用于分子内环氧化物裂解反应。连接链长度，取代方式，反应溶剂，

  DOI：

  10.1016/0040-4020(89)80072-9

文献信息

• Rieke, Reuben D.; Dawson, Bryan T.; Stack, Douglas E., Synthetic Communications, 1990, vol. 20, # 17, p. 2711 - 2721
  作者：Rieke, Reuben D.、Dawson, Bryan T.、Stack, Douglas E.、Stinn, Dean E.

  DOI：——

  日期：——
• Preparation and chemistry of the active copper species derived from CuI.cntdot.PBu3, CuI.cntdot.PPh3, and CuCN.cntdot.nLiX complexes
  作者：Reuben D. Rieke、Douglas E. Stack、Bryan T. Dawson、Tse Chong Wu

  DOI：10.1021/jo00061a023

  日期：1993.4

  The preparation of highly reactive copper by the reduction of CuI.PBu3, CuI.PPh3, and CuCN-nLiX copper(I) complexes with the preformed lithium naphthalenide is described. It was found, for all three Cu(I) complexes, that the reduction temperature proved crucial to reactivity of the zerovalent copper species as measured by the ability of the active copper to undergo oxidative addition to carbon-halogen bonds. The lower the reduction temperature the more reactive the zerovalent copper species becomes. The low-temperature reduction allows for the formation of highly reactive copper from CuCN.nLiX complexes. This active copper species undergoes oxidative addition to alkyl and aryl bromides in high yield to form the corresponding organocopper reagent directly without the need for other organometallic precursors. Moreover, the alkyl and aryl bromides can contain a wide range of functional groups as they are not affected in the oxidative addition step. The functionalized organocopper reagents derived from CuCN-nLiX based active copper are the reagent of choice in the cross-coupling of acid chlorides to produce ketones as well as the 1,4-addition reaction with enones. The lack of phosphines associated with organocopper reagents stemming from CuCN-based active copper makes product isolation more facile. While the functionalized organocopper reagents derived from CuCN.nLiX complexes provide higher isolated yields in the formentioned reactions, they are not nucleophilic enough to undergo inter- or intramolecular epoxide openings. The use of both CuI.PBu3 and CuI.PPh3 Cu(I) complexes in the intramolecular epoxide openings of aryl bromoepoxides is presented. The regiochemistry, endo vs. exo, was shown to be affected by the Cu(I) complex used to generate the active copper species, the solvent, and the pattern of substitution around the epoxide moiety. The active copper species as well as the the resulting organocopper reagents derived from both CuI.PBu3 and CuCN-nLiX were investigated using both P-31 and C-13 NMR. The data from P-31 NMR investigation held some evidence for a highly reduced copper(0)-phosphine complex while the C-13 studies of the CuCN-nLiX complexes indicated that these species have limited solubility in THF.
• Direct formation and reaction of thienyl-based organocopper reagents
  作者：Reuben D. Rieke、Walter R. Klein、Tse Chong Wu

  DOI：10.1021/jo00061a024

  日期：1993.4

  The preparation of a highly reactive zerovalent copper complex by the direct reduction of lithium (2-thienylcyano)cuprate with preformed lithium naphthalenide is described. This active copper species oxidatively adds to carbon-halogen bonds to form organocopper reagents. The ability to directly form the organocopper reagent from organic halides and active copper allows for the incorporation of a wide variety of functionalities to be present in the organic halides and the organocopper reagents. Significantly, this formulation of active copper was able to oxidatively add to allyl chlorides and acetates at low temperatures to allow the direct formation of allylic organocopper reagents without Wurtz-type homocoupling. These functionalized organocopper compounds are able to undergo a variety of reactions, such as cross-coupling with acid chlorides, 1,4-conjugate addition with alpha,beta-unsaturated carbonyl compounds, and intermolecular and intramolecular epoxide-opening reactions. Subsequently, this copper species avoids the use of phosphine ligands affording the product isolation much more convenient than with phosphine-based organocopper reagents.
• Direct formation of functionalized alkylcopper reagents from alkyl halides using activated copper. Conjugate addition reactions with 2-cyclohexen-1-one
  作者：Richard M. Wehmeyer、Reuben D. Rieke

  DOI：10.1021/jo00231a049

  日期：1987.10
• RIEKE, REUBEN D.;WEHMEYER, RICHARD M.;WU, TSE-CHONG;EBERT, GREG W., TETRAHEDRON, 45,(1989) N, C. 443-454
  作者：RIEKE, REUBEN D.、WEHMEYER, RICHARD M.、WU, TSE-CHONG、EBERT, GREG W.

  DOI：——

  日期：——