(3S)-3-isopropylcyclohexanone | 74006-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-3-isopropylcyclohexanone
• 英文别名: (S)-3-isopropylcyclohexanone；(3S)-3-(Propan-2-yl)cyclohexan-1-one；(3S)-3-propan-2-ylcyclohexan-1-one
• CAS: 74006-75-0
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: AFFBXUKVORMWSC-QMMMGPOBSA-N

物化性质

• 沸点：
  195.6±8.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (3S)-3-isopropylcyclohexanone 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-1-Isopropyl-cyclohexanol-⁽³⁾
  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-异丙基-1-环己酮 在 HLAD-NADH 作用下， 生成 (3S)-3-isopropylcyclohexanone
  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

• 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。
• Catalytic Enantioselective Conjugate Addition of Grignard Reagents to Cyclic Enones Using<i>C</i>₁-1,1′-Bisisoquinoline-Based Chiral Ligands
  作者：Gao Qi、Zaher M. A. Judeh

  DOI：10.1080/00397911.2010.541969

  日期：2012.6

  Abstract New highly constrained chiral C 1-1,1′-bisisoquinoline ligands were examined in the enantioselective conjugate addition of Grignard reagents to cyclohexenone and cyclopentenone. The desired 1,4-adducts were obtained in excellent yield and moderate enantiomeric excess (up to 35%). GRAPHICAL ABSTRACT

  摘要 在格氏试剂与环己烯酮和环戊烯酮的对映选择性共轭加成中，研究了新的高度受限的手性 C 1-1,1'-双异喹啉配体。以极好的收率和适度的对映体过量（高达 35%）获得了所需的 1,4-加合物。图形概要
• Stereochemical Insights into the Anaerobic Degradation of 4‐Isopropylbenzoyl‐CoA in the Denitrifying Bacterium Strain pCyN1
  作者：Julian Küppers、Patrick Becker、René Jarling、Marvin Dörries、Nevenka Cakić、Marc Schmidtmann、Jens Christoffers、Ralf Rabus、Heinz Wilkes

  DOI：10.1002/chem.201805837

  日期：2019.3.27

  reductase (BCR) as known from Thauera aromatica K172 and (ii) a modified β‐oxidation pathway yielding 3‐isopropylpimeloyl‐CoA analogously to benzoyl‐CoA degradation in Rhodopseudomonas palustris. Reference standards of all four diastereoisomers of 2‐hydroxy‐4‐isopropylcyclohexane‐1‐carboxylate as well as both enantiomers of 3‐isopropylpimelate were obtained by stereoselective syntheses via methyl 4‐isopr

  对苯二酚在厌氧条件下降解的两种中间体（1 S，2 S，4 S）-2-羟基-4-异丙基环己烷-1-羧酸盐和（S）-3-异丙基庚二酸酯的组成和绝对构型报道了芳香芳香杆菌pCyN1。这些中间体（作为CoA酯）参与了甲基羟基化形成的4-异丙基苯甲酰基-CoA的进一步降解以及对甲基苯丙氨酸的后续氧化。蛋白质组学研究表明4-异丙基苯甲酰辅酶A降解涉及（i）一种新的I类苯甲酰辅酶A还原酶（BCR）成员，如Thauera aromaa所知K172和（ii）修饰的β-氧化途径产生了3-异丙基庚二酰-CoA，类似于在拟南芥中的苯甲酰-CoA降解。通过4-异丙基-2--2-氧代环己烷-1-甲酸甲酯的立体选择性合成，获得了2-羟基-4-异丙基环己烷-1-甲酸的所有四种非对映异构体的参考标准以及3-异丙基庚二酸酯的两种对映体。带有异丙基的立体异构中心是通过铑催化的不对称共轭加成反应建立的。X射线晶体学揭示了在2-羟
• New bidentate alkoxy-NHC ligands for enantioselective copper-catalysed conjugate addition
  作者：Hervé Clavier、Ludovic Coutable、Jean-Claude Guillemin、Marc Mauduit

  DOI：10.1016/j.tetasy.2005.01.015

  日期：2005.3

  Chiral alkoxy-imidazolinium salts are easily available via a five-step procedure starting from β-aminoalcohols. This new family of alkoxy-N-heterocyclic carbene (NHC) precursors is shown to be highly active in the enantioselective copper-catalysed conjugate addition to cyclic enones. Complete conversion with low catalyst loading and good enantiomeric excesses up to 93% were obtained at room temperature

  手性烷氧基-咪唑啉鎓盐很容易通过从β-氨基醇开始的五步操作获得。该新的烷氧基-N-杂环卡宾（NHC）前体家族在对环烯酮的对映选择性铜催化共轭加成中表现出很高的活性。在室温下可获得低催化剂负载量和高达93％的良好对映体过量的完全转化。
• General Method for the Expedient Synthesis of Salt-Free Diorganozinc Reagents Using Zinc Methoxide
  作者：Alexandre Côté、André B. Charette

  DOI：10.1021/ja710864p

  日期：2008.3.1

  Zn(OMe)2 with readily available Grignard reagents, it was possible to induce the complete precipitation of magnesium salts and then obtain salt-free diorganozinc reagents after centrifugation/filtration. This practical method to generate dialkylzinc reagents as well as mixed diorganozinc reagents was successfully tested in various catalytic enantioselective reactions, proving the purity of the product and

  反离子的作用对镁盐在 Et2O 中的溶解度有很大影响。通过将 Zn(OMe)2 与容易获得的格氏试剂反应，可以诱导镁盐完全沉淀，然后在离心/过滤后获得不含盐的二有机锌试剂。这种生产二烷基锌试剂以及混合二有机锌试剂的实用方法在各种催化对映选择性反应中得到成功测试，证明了产品的纯度及其合成用途。