3-戊基环己烷-1-酮 | 69824-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-戊基环己烷-1-酮
• 英文名称: 3-pentyl-cyclohexanone
• 英文别名: 3-pentylcyclohexanone；5-n-pentylcyclohexanone；3-Pentylcyclohexan-1-one
• CAS: 69824-92-6
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: MVBUXNZHMMAGGG-UHFFFAOYSA-N

物化性质

• 沸点：
  237.1±8.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-戊基环己烷-1-酮 生成 (3R)-n-pentyl-cyclohexanone
  参考文献：
  名称：

  Osselaer, T. A. Van; Lemiere, G. L.; Lepoivre, J. A., Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 2, p. 133 - 150

  摘要：

  DOI：
• 作为产物：
  描述：

  2-环己烯-1-酮 、 dipentylzinc 在 N-甲基吡咯烷酮 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到3-戊基环己烷-1-酮
  参考文献：
  名称：

  Uncatalyzed conjugate additions of diorganozincs in N-methylpyrrolidinone

  摘要：

  Diorganozincs efficiently add to enones, unsaturated nitriles and nitroolefins in a mixture of THF and NMP furnishing the corresponding Michael adducts in good to excellent yields. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00915-x

文献信息

• Organocopper reagents in dimethyl sulfide
  作者：Steven H. Bertz、Gary Dabbagh

  DOI：10.1016/0040-4020(89)80070-5

  日期：1989.1

  Organocopper(I) reagents, RCu, are both more stable and more reactive when prepared in dimethyl sulfide instead of ether or tetrahydrofuran. A wide range of Li reagents has been investigated with good results, as has a selection of Grignard reagents. Excellent yields of products are observed with typical substrates such as α,β-unsaturated ketones and acid chlorides.

  用二甲基硫醚代替醚或四氢呋喃制备有机铜（I）试剂RCu既更稳定，也更具反应性。已经研究了多种Li试剂，以及精选的Grignard试剂，均取得了良好的效果。使用典型的底物，例如α，β-不饱和酮和酰氯，可以观察到极好的产品收率。
• Neopentyl and Neophyl Groups: New Nontransferable Groups for Organocopper and Organozinc Chemistry
  作者：Christian Lutz、Philip Jones、Paul Knochel

  DOI：10.1055/s-1999-3387

  日期：1999.2

  Neopentyl and Neophyl groups have been found to be excellent nontransferable groups for organozinc and organocopper chemistry. We have shown that mixed diorganozincs of the type FG-R-Zn(CH2CMe2R) can be used advantageously for the enantioselective addition to aldehydes. These mixed copper or zinc reagents are also found to be very efficient in the Michael addition to various activated alkenes.

  研究发现，新戊基和新苯基是一类优良的非转移性基团，适用于有机锌和有机铜化学。我们已经证明，类型为 FG-R-Zn(CH2CMe2R) 的混合二有机锌可以用于对醛的对映选择性加成。这些混合铜或锌试剂在向各种活化烯烃的迈克尔加成中也表现出非常高的效率。
• Ultrasound in organic synthesis 16. Optimisation of the conjugate additions to α,β-unsaturated carbonyl compounds in aqueous media.
  作者：J.L. Luche、C. Allavena

  DOI：10.1016/s0040-4039(00)82870-1

  日期：——

  Optimisation of the conjugate addition of alkyl groups to α-enones under sonochemical conditions can be effected, especially by a proper choice of the solvent, most probably because of its structural properties.

  共轭加成烷基以声化学条件下α-烯酮的优化可以实现，特别是通过溶剂的适当选择，因为它的结构特性的最有可能。
• Regioselective Iridium-Catalyzed Asymmetric Monohydrogenation of 1,4-Dienes
  作者：Jianguo Liu、Suppachai Krajangsri、Thishana Singh、Giulia De Seriis、Napasawan Chumnanvej、Haibo Wu、Pher G. Andersson

  DOI：10.1021/jacs.7b06829

  日期：2017.10.18

  A highly efficient regio- and enantioselective monohydrogenation of 1,4-dienes has been realized using an iridium catalyst with a chiral N,P-ligand under mild conditions. The substrate scope was studied and included both unfunctionalized as well as functionalized substituents on the meta- or para-position. Substrates having substituents with functionalities such as silyl protected alcohols or ketals

  使用带有手性 N,P-配体的铱催化剂在温和条件下实现了 1,4-二烯的高效区域选择性和对映选择性单氢化。研究了底物范围并包括间位或对位上的未官能化和官能化取代基。具有取代基的底物如甲硅烷基保护的醇或缩酮以高区域选择性和高对映体过量（高达 98% ee）单氢化。
• A New Method for Synthesis of Functionalized Organozinc-Copper(I) Reagents and Their 1,4-Addition Reaction with Enones
  作者：Yulai Hu、Jianhua Yu、Shiyan Yang、Jin-Xian Wang、Yuanqi Yin

  DOI：10.1080/00397919808004854

  日期：1998.8

  Abstract The transmetalation of functionalized organozinc iodides with Cu(OAc)2 in THF provides a new convenient method for the preparation of functionalized organozinc-copper(I) reagents FG-RCu(OAc)ZnI which ultimately undergo 1,4-addition reaction with enones to give the products in good to excellent yields.

  摘要 功能化有机碘化物与 Cu(OAc)2 在 THF 中的金属转移为制备功能化有机锌铜 (I) 试剂 FG-RCu(OAc)ZnI 提供了一种新的便捷方法，该试剂最终与烯酮进行 1,4-加成反应。使产品具有良好的产量。