3-hexylcyclohexan-1-one | 69824-93-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hexylcyclohexan-1-one
• 英文别名: 3-hexylcyclohexanone
• CAS: 69824-93-7
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: ADCQSWBYEZGBTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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-hexylcyclohexan-1-one 在 Candida antarctica lipase 、 双氧水 、 肉豆蔻酸 作用下， 以 甲苯 为溶剂， 反应 144.0h， 生成 6-Hexyl-oxepan-2-one 、 4-Hexyl-oxepan-2-one
  参考文献：
  名称：

  Lemoult, Stephanie C.; Richardson, Paul F.; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1995, # 2, p. 89 - 92

  摘要：

  DOI：
• 作为产物：
  描述：

  2-环己烯-1-酮 、 1-碘己烷 在 indium(III) chloride 、 indium 、 copper(l) iodide 作用下， 以 水 为溶剂， 反应 24.0h， 以45%的产率得到3-hexylcyclohexan-1-one
  参考文献：
  名称：

  Indium/copper-mediated conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds in water

  摘要：

  An efficient method for the conjugate addition of unactivated alkyl iodides to alpha,beta-Unsaturated carbonyl compounds using indium/copper in water is described. The reactions proceed more efficiently in water than in organic solvents. In, CuI, and InCl3 are all essential for efficient reaction. Formation of a symmetrical vic-diarylalkane is observed when an aryl-substituted alkene is used as substrate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.079

文献信息

• Direct Copper(I) Iodide Dimethyl Sulfide Catalyzed Conjugate Addition of Alkenyl Groups from Vinylzirconocene Reagents
  作者：Amer El-Batta、Taleb R. Hage、Steve Plotkin、Mikael Bergdahl

  DOI：10.1021/ol036141y

  日期：2004.1.1

  text] CuI.0.75DMS complex is an excellent catalyst for the direct conjugate addition of alkenyl groups from vinylzirconocene reagents to alpha,beta-unsaturated aldehydes and ketones. The presence of the catalyst with an alkenylzirconocene, at +40 degrees C in THF, circumvents the need for making discrete alkenylcopper reagents. The catalyst is superior in terms of product yields and alkene flexibility

  [反应：见正文] CuI.0.75DMS络合物是将乙烯基锆茂试剂中的烯基直接共轭加成至α，β-不饱和醛和酮的极佳催化剂。在THF中，在+ 40℃下，具有烯基锆茂的催化剂的存在避免了制备离散的烯基铜试剂的需要。与其他铜（I）源以及镍（II）催化的共轭物加成相比，该催化剂在产物收率和烯烃柔韧性方面具有优势。这个简单的一锅法显示仅需要1当量的乙烯基锆茂。
• Heterogeneous double-activation catalysis: Rh complex and tertiary amine on the same solid surface for the 1,4-addition reaction of aryl- and alkylboronic acids
  作者：Hiroto Noda、Ken Motokura、Wang-Jae Chun、Akimitsu Miyaji、Sho Yamaguchi、Toshihide Baba

  DOI：10.1039/c5cy00133a

  日期：——

  Double-activation catalysis by a rhodium complex/tertiary amine catalyst for the 1,4-addition of organoboronic acids was investigated. A rhodium complex and a tertiary amine were co-immobilized on the same silica surface by silane-coupling reactions followed by complexation of the Rh species. Structures of the Rh complex and tertiary amine on the silica surface were determined by solid-state 13C and

  研究了铑配合物/叔胺催化剂对有机硼酸的1,4-加成的双活化催化作用。通过硅烷偶联反应将铑配合物和叔胺共固定在同一二氧化硅表面上，然后使Rh物种络合。通过固态13 C和29 Si MAS NMR，XAFS和XPS测量确定二氧化硅表面上的Rh络合物和叔胺的结构。固定化的叔胺加速了Rh催化的苯基硼酸向环己烯酮的1,4-加成反应。固态11阐明了锚固叔胺在1,4-加成反应中的作用B MAS NMR：它激活芳基硼酸形成四配位的硼物种，然后加速Rh络合物催化的1,4-加成中的金属转移步骤。二氧化硅负载的Rh络合物/叔胺催化剂体系可适用于各种芳基-甚至烷基-硼酸的反应。
• ASYMMETRIC SYNTHESIS OF ORGANIC COMPOUNDS
  申请人：Isis Innovation Limited

  公开号：US20140303385A1

  公开（公告）日：2014-10-09

  The present invention provides processes for the production of chiral compounds in a stereoisomeric excess. The present processes involve reacting a hydrometallated alkene compound with a compound comprising a conjugated-bond system under conditions such that the compounds undergo an asymmetric 1,4- or 1,6-conjugate addition reaction, generating a chiral compound in a stereoisomeric excess. The reaction is performed in the presence of a metal catalyst, which catalyst preferably comprises a non-racemic chiral ligand.

  本发明提供了用于在立体异构体过量中生产手性化合物的工艺。目前的工艺涉及将氢金属化的烯烃化合物与包含共轭键系统的化合物在条件下反应，使得这些化合物经历不对称的1,4-或1,6-共轭加成反应，生成手性化合物的立体异构体过量。反应在金属催化剂存在下进行，该催化剂最好包括非外消旋手性配体。
• Copper-catalyzed conjugate additions of organozirconocenes. Synthetic and mechanistic studies.
  作者：Peter Wipf、Wenjing Xu、Jacqueline H. Smitrovich、Roman Lehmann、Luigi M. Venanzi

  DOI：10.1016/s0040-4020(01)85058-4

  日期：1994.2

  broad range of functional groups are tolerated in the conjugate addition process. Unsaturated N-acyl oxazolidinones give high diastereoselectivities for the formation of the new asymmetric carbon. The resulting zirconium enolates can be used for tandem aldol addition reactions to aldehydes. Depending on the type of copper salt used, slow or fast formation of copper mirror occurs, but no intermediate

  在3–10 mol％的Cu（l）盐（例如CuBr·S Me 2或CuCN）存在下，烷基锆茂金属很容易添加到α，β-不饱和酮，醛和砜中。反应产率对路易斯酸和碱的存在敏感。在共轭加成过程中可以耐受立体位阻以及广泛的官能团。不饱和氮-酰基恶唑烷酮类对形成新的不对称碳具有高的非对映选择性。所得的烯醇锆可用于醛醇的串联醇醛加成反应。根据所用铜盐的类型，会发生缓慢或快速形成铜镜的现象，但是在光谱学上没有检测到中间的铜物种。因此，提出了一种机理，该机理涉及路易斯酸性的锆茂并烯的烯酮络合，然后烷基取代基的内球转移到螯合的Cu（l）上。
• [EN] ASYMMETRIC SYNTHESIS OF ORGANIC COMPOUNDS<br/>[FR] SYNTHÈSE ASYMÉTRIQUE DE COMPOSÉS ORGANIQUES
  申请人：ISIS INNOVATION

  公开号：WO2013054131A1

  公开（公告）日：2013-04-18

  The present invention provides processes for the production of chiral compounds in a stereoisomeric excess. The present processes involve reacting a hydrometallated alkene compound with a compound comprising a conjugated -bond system under conditions such that the compounds undergo an asymmetric 1,4- or 1,6-conjugate addition reaction, generating a chiral compound in a stereoisomeric excess. The reaction is performed in the presence of a metal catalyst, which catalyst preferably comprises a non-racemic chiral ligand.

  本发明提供了用于在立体异构物过量中生产手性化合物的过程。目前的过程涉及将一个氢金属化的烯烃化合物与包含一个共轭-键系统的化合物在条件下反应，使得这些化合物经历不对称的1,4-或1,6-共轭加成反应，生成手性化合物的立体异构物过量。反应在金属催化剂存在下进行，该催化剂最好包括一个非外消旋手性配体。