3-n-octylcyclohexanone | 57242-85-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-n-octylcyclohexanone
• 英文别名: 3-n-octylcycohexanone；3-octylcyclohexanone；3-octylcyclohexan-1-one
• CAS: 57242-85-0
• 化学式: C₁₄H₂₆O
• 分子量: 210.36
• InChiKey: FOHJLYHYSMKQBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  285.3±8.0 °C(Predicted)
• 密度：
  0.878±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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-氯辛烷 在 cobalt(II) 1,6-bis(2-hydroxyphenyl)-2,5-diaza-3,3,4,4-tetramethylhexa-1,5-diene 、 lithium chloride 、 正丁醇 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以54 %的产率得到3-n-octylcyclohexanone
  参考文献：
  名称：

  钴催化未活化的烷基氯与共轭烯烃的电还原烷基化

  摘要：

  据报道，温和的电催化系统可用于伯、仲或叔烷基氯与共轭烯烃的还原烷基化。

  DOI：

  10.1002/anie.202313830

文献信息

• CuX₃Li₂-catalysed conjugate addition of dialkylmagnesium reagents to α,β-unsaturated carbonyl compounds
  作者：Manfred T. Reetz、Alois Kindler

  DOI：10.1039/c39940002509

  日期：——

  Copper salts of the type CuX3Li2(X = halogen) catalyse the conjugate addition of dialkylmagnesium compounds to α,β-unsaturated carbonyl compounds in the presence or absence of Me3SiCl as an additive, the organomagnesium compounds being prepared from α-olefins, hydrogen and magnesium according to the procedure of Bogdanović.

  在存在或不存在作为添加剂的Me 3 SiCl的情况下，CuX 3 Li 2类型的铜盐（X =卤素）催化二烷基镁化合物共轭加成到α，β-不饱和羰基化合物上，有机镁化合物由α-根据Bogdanović的程序制备烯烃，氢和镁。
• New organocopper reagents prepared utilizing highly reactive copper
  作者：Reuben D. Rieke、Richard M. Wehmeyer、Tse-Chong Wu、Greg W. Ebert

  DOI：10.1016/0040-4020(89)80072-9

  日期：1989.1

  Highly reactive copper solutions have been prepared by the lithium naphthalide reduction of copper(I) iodide/trialkylphosphine complexes. These activated copper solutions will react with organic halides under very mild conditions to form stable organocopper reagents. Significantly, the organocopper reagents can contain considerable functionalities such as ester, nitrile, chloride, epoxide, and ketone

  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，
• Soluble highly reactive form of calcium and reagents thereof
  申请人：Board of Regents of the University of Nebraska

  公开号：US05384078A1

  公开（公告）日：1995-01-24

  A soluble highly reactive form of calcium, prepared from Ca(II) salts and a reducing agent in ethereal, polyethereal, or hydrocarbon solvents, is presented. This form of calcium can be used in the preparation of organocalcium reagents. The organocalcium reagents resulting from the reaction of the soluble highly reactive calcium with organic compounds containing either halide, cyanide, a 1,3-diene, or a polyunsaturated functionality, are stable, useful reagents for organic synthesis. The organocalcium halide reagents undergo Grignard-type reactions. They also undergo reactions with Cu(I) salts to form organocalcium cuprate reagents. The organocalcium cuprate reagents undergo a variety of cross-coupling reactions. The soluble highly reactive calcium reacts with 1,3-dienes to yield the corresponding 2-butene-1,4-diylcalcium complexes. These bis-organocalcium reagents can undergo dialkylation reactions with .alpha.,.omega.-alkylene dihalides and dichlorosilanes to form the corresponding 3-, 5-, and 6-membered ring derivatives. The soluble highly reactive calcium also reacts with organic dihalides to form mono- or diorganocalcium compounds which can be converted into a wide variety of polymers.

  这是一种可溶性的高反应性钙形式，由Ca（II）盐和还原剂在乙醚，聚醚或烃类溶剂中制备。这种钙形式可用于有机钙试剂的制备。与含有卤素，氰基，1,3-二烯或多不饱和官能团的有机化合物反应产生的有机钙试剂稳定，是有机合成中有用的试剂。有机钙卤试剂经历格氏试剂反应。它们还与Cu（I）盐反应形成有机钙杯酸盐试剂。有机钙杯酸盐试剂经历各种交叉偶联反应。可溶性高反应性钙与1,3-二烯反应产生相应的2-丁烯-1,4-二基钙配合物。这些双有机钙试剂可以与α，ω-烷基二卤化物和二氯硅烷发生二烷基化反应，形成相应的3，5和6元环衍生物。可溶性高反应性钙还与有机二卤化物反应形成单或双有机钙化合物，可转化为各种聚合物。
• 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.