(E)-1-cyclohexyl-1-butene

• 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)-1-cyclohexyl-1-butene
• 英文别名: 1-cyclohexyl-1-butene；(E)-CyCH=CHEt；cyclohexylbutene；Butenylcyclohexane；[(E)-but-1-enyl]cyclohexane
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: QLCXXXXMRVOLRN-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-1-cyclohexyl-1-butene 在 (1,3-dimethylimidazol-2-ylidene)borane 、 双三氟甲烷磺酰亚胺 、 双氧水 、 sodium hydroxide 作用下， 以 1,2-二氯乙烷 、 甲醇 、 水 为溶剂， 反应 40.0h， 生成 alpha-甲基环己烷丙醇 、 4-环己基-1-丁醇
  参考文献：
  名称：

  Borenium Ion Catalyzed Hydroboration of Alkenes with N-Heterocyclic Carbene-Boranes

  摘要：

  Treatment of alkenes such as 3-hexene, 3-octene, and 1-cyclohexyl-1-butene with the N-heterocyclic carbene (NHC)-derived borane 2 and catalytic HNTf2 (Tf = trifluoromethanesulfonyl (CF3SO2)) effects hydroboration at room temperature. With 3-hexene, surprisingly facile migration of the boron atom from C(3) of the hexyl group to C(2) was observed over a time scale of minutes to hours. Oxidative workup gave a mixture of alcohols containing 2-hexanol as the major product. A similar preference for the C(2) alcohol was observed after oxidative workup of the 3-octene and 1-cyclohexyl-1-butene hydroborations. NHC-borenium cations (or functional equivalents) are postulated as the species that accomplish the hydroborations, and the C(2) selective migrations are attributed to the four center interconversion of borenium cations with cationic NHC-borane-olefin pi-complexes.

  DOI：

  10.1021/ja305061c
• 作为产物：
  描述：

  2-Chlorobutanal 、 环己基溴化镁 以50%的产率得到
  参考文献：
  名称：

  BARLUENGA J.; YUS M.; CONCELLON J. M.; BERNARD P., J. CHEM. RES. SYNOP., 1980, NO 2, 41/J. CHEM. RES. MIKROFICHE, 0677-0692

  摘要：

  DOI：

文献信息

• Regioselective Hydroalumination of Allenes and Their Synthetic Application
  作者：Shigeru Nagahara、Keiji Maruoka、Hisashi Yamamoto

  DOI：10.1246/bcsj.66.3783

  日期：1993.12

  The hydroalumination of a terminal allene, 1,2-nonadiene, with LiAlH4 in THF using [TiCl2(Cp)2], TiCl4, TiCl3, ZrCl4, and [ZrCl2(Cp)2] catalysts afforded a wide variety of deuterated species by quenching hydroalumination products with D2O, while PhB(OH)2-catalyzed hydroalumination with AlHCl2 in ether gave >95% pure 1-nonene-3-d as predominant product (92%) in high yield. The allylation of benzaldehyde

  使用 [TiCl2(Cp)2]、TiCl4、TiCl3、ZrCl4 和 [ZrCl2(Cp)2] 催化剂在 THF 中用 LiAlH4 对末端丙二烯、1,2-壬二烯进行加氢铝化，通过淬灭提供了多种氘化物质用 D2O 加氢铝化产物，而 PhB(OH)2 催化加氢铝化用 AlHCl2 在乙醚中以高产率得到>95% 纯度的 1-壬烯-3-d 作为主要产物 (92%)。使用PhB(OH) 2 催化的氢铝化产物使苯甲醛烯丙基化表明所得的氢铝化产物可能是烯丙基铝化合物，2-壬烯基二氯化铝。使用这种烯丙基铝化合物进行反式肉桂醛的烯丙基化反应具有高区域选择性，酮官能团保持完整。环氧化物的烯丙基化开环反应的区域选择性较小。
• Enantioselective Copper-Mediated Allylic Substitution with Grignard Reagents Employing a Chiral Reagent-Directing Leaving Group
  作者：Bernhard Breit、Daniel Breuninger

  DOI：10.1055/s-2004-831247

  日期：——

  Enantioselective copper-mediated allylic substitution with Grignard reagents was achieved employing the ortho-diphenylphosphanylferrocene carboxylate (o-DPPF) system as a planar chiral reagent-directing leaving group. Careful optimization of reaction parameters resulted in excellent regioselectivities and enantioselectivies of up to 95% ee.

  利用邻二苯基膦酰二茂铁羧酸酯（邻DPPF）体系作为平面手性试剂导向离去基团，实现了铜介导的烯丙基取代格氏试剂的对映体选择性。通过对反应参数的精心优化，获得了极佳的区域选择性和高达 95% ee 的对映选择性。
• Copper catalyzed enantioselective allylic substitution by MeMgX
  作者：Karine Tissot-Croset、Alexandre Alexakis

  DOI：10.1016/j.tetlet.2004.07.114

  日期：2004.9

  Methyl Grignard undergoes highly regio (>90/10) and enantioselective (ee 91-96%) copper catalyzed allylic substitution on cinnamyl-type chlorides. 3% of CuBr and 3.3% of a chiral phosphoramidite ligand are sufficient for a complete reaction. The synthesis of a precursor of (+)-Naproxen is described. The reaction can be extended to alkyl substituted allylic chlorides (ee 72%). (C) 2004 Elsevier Ltd. All rights reserved.
• Metzger, Juergen O.; Blumenstein, Michael, Chemische Berichte, 1993, vol. 126, # 11, p. 2493 - 2500
  作者：Metzger, Juergen O.、Blumenstein, Michael

  DOI：——

  日期：——
• BARLUENGA, J.;YUS, M.;CONCELLON, M.;BERNAD, P., J. ORG. CHEM., 1983, 48, N 4, 609-611
  作者：BARLUENGA, J.、YUS, M.、CONCELLON, M.、BERNAD, P.

  DOI：——

  日期：——