(E)-1-cyclohexylpentene | 74044-28-3

• 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)-1-cyclohexylpentene
• 英文别名: (E)-pent-1-en-1-ylcyclohexane；(1E)-1-pentenylcyclohexane；[(E)-pent-1-enyl]cyclohexane
• CAS: 74044-28-3
• 化学式: C₁₁H₂₀
• 分子量: 152.28
• InChiKey: RQPUZGKLFDPSJD-VMPITWQZSA-N

物化性质

• 沸点：
  198.6±7.0 °C(Predicted)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  三甲氧基硅烷 、 (E)-1-cyclohexylpentene 在 2C₄H₉O^(1-)*Ni⁽²⁺⁾*(x)KCl 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以69%的产率得到(5-cyclohexylpentyl)trimethoxysilane
  参考文献：
  名称：

  一种易于获得的镍纳米粒子催化剂，用于叔硅烷与烯烃的氢硅烷化反应

  摘要：

  已经开发出了第一种用于烯烃与商业相关的叔硅烷氢化硅烷化的高效且非贵重的纳米颗粒催化剂。的镍纳米粒子催化剂在原位制备从一个简单的镍的醇盐预催化剂的Ni（O吨丁基）2 ⋅x氯化钾。该催化剂对未活化的末端烯烃的抗马尔可夫尼科夫氢化硅烷化和内部烯烃的异构化氢化硅烷化表现出很高的活性。该催化剂可用于由内部和末端烯烃异构体的混合物合成单个末端烷基硅烷，并远程官能化衍生自脂肪酸的内部烯烃。

  DOI：

  10.1002/anie.201606832
• 作为产物：
  描述：

  环己甲酸乙酯 在 2,2,6,6-四甲基哌啶 、 锂硼氢 、 正丁基锂 、 cerium(III) chloride 、 potassium hydride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (E)-1-cyclohexylpentene
  参考文献：
  名称：

  Opposite Stereochemical Effects Exerted by CeCl3 and TiCl4 on the Lewis Acid Mediated Reduction of α-Alkyl-β-ketophosphine Oxides with Metallic Hydrides: A Highly Stereoselective Protocol for the Synthesis of syn and anti α-alkyl-β-Hydroxyphosphine Oxides

  摘要：

  AbstractA general, highly efficient methodology for obtaining both syn and anti β‐hydroxyphosphine oxides by reduction of the corresponding β‐ketophosphine oxides is described. The nature of the Lewis acid was found to be pivotal in determining the outcome of these reactions. Strongly chelating TiCl4 led to the anti isomer in high diastereoisomeric excess in noncoordinating solvents (CH2Cl2) at ‐78°C with BH3/py as reducing agent, while nonchelating CeCl3 gave a high excess of the syn isomer in coordinating solvents (THF) at the same temperature with LiBH4 as reducing agent. In the latter case, CeCl3 is essential in achieving high yields and stereoselectivity, since it allows the reaction to be performed at low temperatures. Otherwise, higher temperatures (0°C) are required, which lower both yields and selectivities. Moreover, each step of the protocol for the synthesis of stereodefined disubstituted olefins from alkylphosphine oxides (Warren's modification of the Horner procedure) has been optimized, and the optimized procedure has been applied to the synthesis of muscalure, the pheromone of the domestic fly.

  DOI：

  10.1002/chem.19970031209

文献信息

• P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation
  作者：Wenrui Xiong、Guangqing Xu、Xinhong Yu、Wenjun Tang

  DOI：10.1021/acs.organomet.9b00194

  日期：2019.10.28

  Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.

  描述了使用P-手性单磷配体在烯丙基溴和烷基格氏试剂之间的不对称铜催化的烯丙基烷基化。在低至0.5mol％的铜负载下，形成具有良好支化/线性选择性和优异对映选择性的一系列带有叔碳或季碳中心的末端烯烃。
• Hindered organoboron groups in organic synthesis. 14. stereoselective synthesis of alkenes by the boron-wittig reaction using aliphatic aldehydes
  作者：Andrew Pelter、Keith Smith、Said Elgendy、Martin Rowlands

  DOI：10.1016/s0040-4039(01)93821-3

  日期：1989.1

  In the presence of HX, carbanions Mes2BCHLiR1 react with aliphatic aldehydes to give alkenes. The stereochemistry of the product alkene depends upon the nature of HX.

  在HX存在下，碳负离子Mes 2 BCHLiR 1与脂族醛反应生成烯烃。产物烯烃的立体化学取决于HX的性质。
• Novel<i>ortho</i>-Alkoxy-Substituted Phosphorus Ylides and Their Stereoselectivity in Witting Reactions
  作者：Suruliappa Jeganathan、Masamitsu Tsukarmoto、Manfred Schlosser

  DOI：10.1055/s-1990-26801

  日期：——

  The stereochemistry of the reactions between tris(2-methoxy-methoxyphenyl)phosphonioethanide (1f), -butanide (2f), and -phenyl-methanide (3f) and a variety of aldehydes was investigated. Ylides having a β-unbranched aliphatic sidechain, such as 2f, and saturated straight-chain aldehydes give olefins with unprecedented cis-selectivity (cis/trans ≍ 200:1).

  三(2-甲氧基甲氧基苯基)膦醯電乙烷錘(1f)、-丁烷錘(2f)和-苯甲烷錘(3f)与一系列醛类反应的立体化学被研究了。具有β-无分支脂肪链的叶立德(如2f)和饱和直链醛类产生前所未有的顺式选择性烯烃(顺/反 ≈ 200:1)。
• Réaction de quelques allènes avec l'hydrure de di-isobutyl-aluminium
  作者：Michel Montury、Jacques Goré

  DOI：10.1016/s0040-4039(00)93622-0

  日期：1980.1

  Reduction of the more substituted of the two double bonds of the allenic linkage can be selectively achieved by the reaction with DIBAH followed by hydrolysis.

  通过与DIBAH反应然后水解，可以选择性地实现降低烯丙基键的两个双键的更多取代基。
• DBP ylides: Wittig reagents for synthesis of E-alkenes from aldehydes
  作者：E. Vedejs、C. Marth

  DOI：10.1016/s0040-4039(00)96322-6

  日期：——

  Phosphorus ylides based on the dibenzophosphole (DBP) ring system convert aldehydes into trans-disubstituted oxaphosphetanes with good to excellent selectivity. Decomposition at 70–110° affords alkenes with E:Z ratios from 6:1 to > 100:1.

  基于二苯并磷腈（DBP）环系统的磷化磷化物可将醛转化为具有良好或优异的选择性的反式二取代的氧杂膦酸酯。在70–110°分解可得到E：Z比为6：1至> 100：1的烯烃。