3-ethylcyclohexanone | 74006-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethylcyclohexanone
• 英文别名: (S)-3-ethylcyclohexanone；(S)-3-ethylcyclohexan-1-one；(3S)-3-ethylcyclohexanone；(3S)-3-ethylcyclohexan-1-one
• CAS: 74006-73-8
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: IEVRHAUJJJBXFH-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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-ethylcyclohexanone 在 1,4-dihydronicotinamide adenine dinucleotide 、 horse liver alcohol dehydrogenase 作用下， 以 乙醇 为溶剂， 以30%的产率得到(+/-)-trans-3-ethyl-cyclohexanol
  参考文献：
  名称：

  Use of shift reagent with MTPA derivatives in19F NMR spectrocopy: IV—Determination of enantiomeric composition for a variety of secondary cycloalkanols. A survey

  摘要：

  AbstractChiral secondary cycloalkanols (monocyclic alcohols) are derivatized to the corresponding (R)‐α‐methoxy‐α‐trifluoromethyl‐α‐phenylacetic acid [(R)‐MTPA] esters and analysed by 19F NMR in the presence of tris(6,6,7,7,8,8,8‐heptafluoro‐2,2‐dimethyl‐3,5‐octanedionato) europium(III) [Eu(fod)3]. Using this method the enantiomeric composition can be measured for several cyclopentanols, cyclohexanols and cycloheptanols, with a variety of substitution patterns. It is shown that a mixture of four stereoisomeric cycloalkanols, such as cis and trans disubstituted alcohols, can be analysed simultaneously.

  DOI：

  10.1002/omr.1270210609
• 作为产物：
  描述：

  3-乙基环己酮 在 HLAD-NADH 作用下， 生成 3-ethylcyclohexanone
  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：

文献信息

• Enantioselective Catalytic Conjugate Addition of Dialkylzinc Reagents using Copper–Phosphoramidite Complexes; Ligand Variation and Non-linear Effects
  作者：Leggy A Arnold、Rosalinde Imbos、Alessandro Mandoli、André H.M de Vries、Robert Naasz、Ben L Feringa

  DOI：10.1016/s0040-4020(00)00142-3

  日期：2000.4

  cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.’s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic

  合成了多种新的手性亚磷酰胺，并在铜催化的对乙基己烯酮和查耳酮的铜催化对映选择性共轭加成中进行了测试，以评估对立体控制至关重要的结构特征。空间要求高的胺部分对于达到高ee是必不可少的。发现查尔酮的对映选择性高达89％，环烯酮的对映选择性高达98％。对具有最佳配体的环己烯酮和查尔酮的非线性效应的研究表明，环状和非环状烯酮均具有明显的非线性效应。
• Sugar-based phosphite and phosphoroamidite ligands for the Cu-catalyzed asymmetric 1,4-addition to enones
  作者：Eva Raluy、Oscar Pàmies、Montserrat Diéguez、Stephane Rosset、Alexander Alexakis

  DOI：10.1016/j.tetasy.2009.09.002

  日期：2009.9

  A modular sugar-based phosphoroamidite L1–L5a–g and phosphite L6–L9a–g ligand library was tested in the asymmetric Cu-catalyzed 1,4-conjugate addition reactions of β-substituted (cyclic and linear) and β,β′-disubstituted (cyclic) enones. The selectivity depended strongly on the configuration of carbon atom C-3, the size of the sugar backbone ring, the flexibility of the ligand backbone, the substituents

  在不对称的铜催化的β-取代的（环状和线性）与β，β'-的1,4-共轭加成反应中，测试了模块化糖基亚磷酰胺L1 - L5a - g和亚磷酸酯L6 - L9a - g配体库二取代（环状）烯酮。选择性很大程度上取决于碳原子C-3的构型，糖主链的大小，配体主链的柔韧性，联芳基亚磷酰胺部分a – g中的取代基和构型，是连接到配体主链和底物结构上的官能团的类型。因此，通过仔细选择配体参数，对环状底物的对映选择性高达60％，对于线性底物的对映选择性高达72％。
• Hemilabile P-Alkene Ligands in Chiral Rhodium and Copper Complexes: Catalytic Asymmetric 1,4 Additions to Enones. 2^,
  作者：Emma Drinkel、Alexander Briceño、Reto Dorta、Romano Dorta

  DOI：10.1021/om100248u

  日期：2010.6.14

  bidentate P-alkene ligands was observed in the presence of Lewis basic solvents, and model compounds of mono- and bis-solvated species (13, 14) were isolated. Cu formed trigonal-planar neutral (15−17) and cationic complexes (18, 19) of the general formulas [CuI(κ1P-alkene)2] and [Cu(κ1P-alkene)2BF4], respectively (P-alkene = 2, 4, 5). The cationic Rh species 11 catalyzed the 1,4-addition of arylboronic

  两个当量手性二苯并[的b，˚F ]氮杂衍生的P-烯烃配体2 - 6每金属，得到单核的Rh（I）和Cu（I）作为催化剂的不对称共轭加成反应，其配合物。的Rh形成正方形平面中性（8 - 10）和阳离子络合物（11，12）通式[的RhCl（κ 1 P-烯烃）（κ 2 P-烯烃）]以及顺式- [铑（κ 2 P-烯）2 ] [BF 4分别]，（P-烯烃= 2，5，6）。在这两种情况下在路易斯碱性溶剂的存在下，观察到双齿P-烯烃配体的烯烃功能的可逆decoordination，和单-和双-溶剂化物种（的模型化合物13，14分离）。Cu而形成三角平面的中性（15 - 17）和阳离子络合物（18，19通式[的CuI（κ）的1 P-烯烃）2 ]和[Cu（上κ 1 P-烯烃）2 BF 4 ]，分别（P-烯烃= 2，4，5）。阳离子Rh物种11催化芳基硼酸向高活性（40°C下的TON = 62）和出色的对映体控
• ORGANIC SALTS AND METHOD FOR PRODUCING CHIRAL ORGANIC COMPOUNDS
  申请人：List Benjamin

  公开号：US20090030216A1

  公开（公告）日：2009-01-29

  The invention relates to a method for producing chiral organic compounds by asymmetric catalysis, using ionic catalysts comprising a chiral catalyst anion. The claimed method is suitable for reactions which are carried out over cationic intermediate stages, such as iminium ions or acyl pyridinium ions. The invention enables the production of chiral compounds with high ee values, that until now could only be obtained by means of costly purification methods.

  该发明涉及一种通过不对称催化制备手性有机化合物的方法，使用包括手性催化剂阴离子的离子催化剂。所述方法适用于在阳离子中间体阶段进行的反应，例如亚胺离子或酰基吡啶离子。该发明实现了具有高ee值的手性化合物的生产，直到现在只能通过昂贵的纯化方法获得。
• Tropanes as Scaffolds for Phosphorus-Olefin Ligands and Their Application in Asymmetric Catalysis
  作者：Sandra Vlahovic、Nicole Schädel、Stefan Tussetschläger、Sabine Laschat

  DOI：10.1002/ejoc.201201539

  日期：2013.3

  reaction with various substrates. The most promising results in both reactions were achieved with ligands 11 and 15, which contain a chiral alkene/achiral P-unit or an achiral alkene/chiral P moiety, respectively, and where the metal is complexed on the exo side of the tropene skeleton. In contrast, ligands with an endo coordination mode showed only low (13) or no activity (12) in all of the 1,4-additions

  托烷衍生的磷-烯烃杂化配体带有 P-单元（手性 BINOL 衍生单元/非手性 PPh2-单元）与托烯骨架（手性/非手性）的各种组合已被合成并用于 Cu 催化的共轭 1,4-二乙基锌与环烯酮的加成以及在 Rh 催化的苯基硼酸（Hayashi-Miyaura 反应）与环状和非环烯酮的 1,4-加成中。而在 Cu 催化的反应中，只获得了中等的产率和 ee 值（高达 49% ee），而在 Hayashi-Miyaura 反应中观察到高达 97% ee 与各种底物。两个反应中最有希望的结果是用配体 11 和 15 实现的，它们分别包含一个手性烯烃/手性 P 单元或一个非手性烯烃/手性 P 部分，并且金属络合在 tropene 骨架的外侧. 相比之下，具有内配位模式的配体在所有 1,4-添加中仅显示低活性 (13) 或无活性 (12)。NMR 和 ESI-MS 实验表明溶液中存在两种阳离子 [RhI(15)2]+