(E)-(oct-1-en-1-yl)cyclohexane | 87393-89-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (E)-(oct-1-en-1-yl)cyclohexane
• 英文别名: (E)-oct-1-en-1-ylcyclohexane；(E)-1-Cyclohexyl-1-octene；1-cyclohexyl-1-octene；[(E)-oct-1-enyl]cyclohexane
• CAS: 87393-89-3
• 化学式: C₁₄H₂₆
• 分子量: 194.36
• InChiKey: RTQQWFWTEINQLG-DHZHZOJOSA-N

物化性质

• 沸点：
  258.4±7.0 °C(Predicted)
• 密度：
  0.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  反式-1-碘-1-辛烯 、 triethylammonium cyclohexylbis(catecholato)silicate 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 氯化镍二甲氧基乙烷 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以74%的产率得到(E)-(oct-1-en-1-yl)cyclohexane
  参考文献：
  名称：

  通过光氧化还原双重催化使烯基卤化物与烷基硅酸盐结合

  摘要：

  通过光氧化还原/镍双重催化进行单电子重金属化，可在非常温和的反应条件下通过烷基自由基的转移来构建C sp 3 –C sp 2键。提出了伯和仲（双-邻苯二酚）烷基硅酸盐与烯基卤化物交叉偶联的一般方法。所开发的方法不仅允许使用烯基溴化物和碘化物，而且还可以使用先前未充分开发的烯基氯。

  DOI：

  10.1021/acs.orglett.6b00024

文献信息

• Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides
  作者：Adam Noble、Stefan J. McCarver、David W. C. MacMillan

  DOI：10.1021/ja511913h

  日期：2015.1.21

  Decarboxylative cross-coupling of alkyl carboxylic acids with vinyl halides has been accomplished through the synergistic merger of photoredox and nickel catalysis. This new methodology has been successfully applied to a variety of α-oxy and α-amino acids, as well as simple hydrocarbon-substituted acids. Diverse vinyl iodides and bromides give rise to vinylation products in high efficiency under mild

  烷基羧酸与乙烯基卤化物的脱羧交叉偶联是通过光氧化还原和镍催化的协同合并实现的。这种新方法已成功应用于各种α-氧基和α-氨基酸，以及简单的烃取代酸。不同的乙烯基碘化物和溴化物在温和、操作简单的反应条件下高效地产生乙烯基化产物。
• A Novel Synthesis of Internal Alkenyldialkylborane by the Reaction of 1-Halo-1-alkenyldialkylborane with Grignard Reagent
  作者：Akira Arase、Masayuki Hoshi、Yuzuru Masuda

  DOI：10.1246/bcsj.57.209

  日期：1984.1

  To synthesize internal alkenyldialkylboranes, coupling reactions were carried out by using 1-halo-l-alkenyldialkylboranes and Grignard reagents. Hydrogen peroxide oxidation and protonolysis with acetic acid of the reaction product revealed that internal (E)-alkenyldialkylborane was formed in 60–90% yield.

  为了合成内部烯基二烷基硼烷，通过使用 1-卤代-l-烯基二烷基硼烷和格氏试剂进行偶联反应。过氧化氢氧化和反应产物的乙酸质子分解表明，内部 (E)-烯基二烷基硼烷以 60-90% 的产率形成。
• A new convenient procedure to prepare organomanganese reagents from organic halides and activated manganese
  作者：Gérard Cahiez、Arnaud Martin、Thomas Delacroix

  DOI：10.1016/s0040-4039(99)01331-3

  日期：1999.8

  A new method to obtain activated manganese metal, especially attractive for large scale preparative organic chemistry, is described. The key point is the use of 2-phenylpyridine as electron carrier to reduce manganese chloride by lithium. The active manganese thus obtained was used to prepare various organomanganese reagents from organic halides. The reactivity of these reagents has been studied (acylation

  描述了一种获得活化的锰金属的新方法，该方法对大规模制备有机化学特别有吸引力。关键是使用2-苯基吡啶作为电子载体，通过锂还原氯化锰。如此获得的活性锰用于由有机卤化物制备各种有机锰试剂。已经研究了这些试剂的反应性（酰化，1,2-或1,4-加成，烷基化和烯基化）。
• Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Aryl Sulfides and Alkenyl Alkyl Sulfides with Alkyl Grignard Reagents Using (<i>Z</i>)-3,3-Dimethyl-1,2-bis(diphenylphosphino)but-1-ene as Ligand
  作者：Hideki Yorimitsu、Koichiro Oshima、Shigenari Kanemura、Azusa Kondoh

  DOI：10.1055/s-2008-1067193

  日期：2008.8

  A combination of nickel(II) acetylacetonate and (Z)-3,3-dimethyl-1,2-bis(diphenylphosphino)but-1-ene catalyzes cross-coupling reactions of alkyl aryl sulfides and alkenyl alkyl sulfides with alkyl Grignard reagents. Not only primary but also secondary alkyl Grignard reagents can be employed.

  乙酰丙酮镍 (II) 和 (Z)-3,3-dimethyl-1,2-bis(diphenylphosphino)but-1-ene 的组合催化烷基芳基硫化物和烯基烷基硫化物与烷基格氏试剂的交叉偶联反应。不仅可以使用伯烷基格氏试剂而且可以使用仲烷基格氏试剂。
• Highly Selective Reactions of Unbiased Alkenyl Halides and Alkylzinc Halides: Negishi-Plus Couplings
  作者：Arkady Krasovskiy、Bruce H. Lipshutz

  DOI：10.1021/ol201307y

  日期：2011.8.5

  High yielding stereo- and chemoselective Pd-catalyzed cross-couplings In THF at room temperature of alkenyl iodides and bromides with primary and secondary alkyl zinc iodides have been developed with the aid of N-methylmidazole as the key additive.