(S)-(-)-4-methyl-2-cyclohexen-1-one | 101758-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(-)-4-methyl-2-cyclohexen-1-one
• 英文别名: (S)-(-)-4-methylcyclohex-2-en-1-one；(S)-(-)-4-methyl-2-cyclohexenone；(4S)-4-Methyl-2-cyclohexenone；(-)-4-methyl-2-cyclohexenone；(S)-4-methyl-2-cyclohexenone；(S)-4-methylcyclohex-2-enone；(4S)-4-methylcyclohex-2-en-1-one
• CAS: 101758-35-4
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: RKSNPTXBQXBXDJ-ZCFIWIBFSA-N

物化性质

• 沸点：
  175.3±10.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (S)-(-)-4-methyl-2-cyclohexen-1-one 以 四氢呋喃 、 正己烷 、 三乙胺 、 苯 为溶剂， 反应 1.5h， 生成 (3R,4R,SS)-1,4-dimethyl-3-(phenylsulfinyl)-1-cyclohexene
  参考文献：
  名称：

  Enantioselective total synthesis of (+)-12,13-epoxytrichothec-9-ene and its antipode

  摘要：

  DOI：

  10.1021/ja00222a036
• 作为产物：
  描述：

  4-methyl-2-cyclohexenone 生成 (S)-(-)-4-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Kinetic resolution in Diels-Alder processes

  摘要：

  Examples of highly efficient kinetic resolutions with the bicyclic chiral cyclopentadiene 1 and several selected cyclic dienophiles are reported. In combination with a thermal retro-Diels-Alder process this procedure provides easy access to both enantiomers of these dienophiles.

  DOI：

  10.1016/s0957-4166(00)86079-6

文献信息

• Chemical synthons and intermediates
  申请人：——

  公开号：US20040138485A1

  公开（公告）日：2004-07-15

  The invention provides novel six and seven-carbon termini-differentiated polypropionate stereotetrads and stereopentads useful in syntheses of natural products. The invention also provides a novel alkylative sulfenylation-desulfonylation process that efficiently transforms enantiopure epoxyvinyl sulfones to syn and anti dienylsulfides in two operations.

  这项发明提供了新颖的六碳和七碳末端差异化的聚丙酸酯立体四聚体和立体五聚体，可用于合成天然产物。该发明还提供了一种新颖的烷基化磺化-去磺化过程，能够高效地将对映纯环氧乙烯基磺酮转化为syn和anti二烯基硫醚，只需两步操作。
• Old Yellow Enzyme-Catalyzed Dehydrogenation of Saturated Ketones
  作者：Matthias Schittmayer、Anton Glieder、Michael K. Uhl、Andreas Winkler、Simone Zach、Jörg H. Schrittwieser、Wolfgang Kroutil、Peter Macheroux、Karl Gruber、Spiros Kambourakis、J. David Rozzell、Margit Winkler

  DOI：10.1002/adsc.201000862

  日期：2011.2.11

  isolated, cloned, heterologously expressed and characterized a thermostable old yellow enzyme (OYE) from Geobacillus kaustophilus. In addition to the expected ‘enone’ reduction, GkOYE also catalyzes the reverse reaction, i.e., the desaturation of CC bonds adjacent to a carbonyl to give the corresponding α,β-unsaturated ketone. The reaction proceeds at the expense of molecular oxygen without the need

  极端微生物的酶由于对各种应激因素的耐受性而一直对生物技术非常感兴趣。我们已经分离，克隆，异源表达并表征了来自嗜碱芽孢杆菌的热稳定的旧黄色酶（OYE）。除预期的“烯酮”还原外，Gk OYE还催化逆反应，即与羰基相邻的CC键脱饱和，得到相应的α，β-不饱和酮。该反应以分子氧为代价而无需烟酰胺辅因子进行，并且代表了对已知化学脱氢方法的环境友好的替代方案。
• Highly Enantioselective Copper-Phosphoramidite Catalyzed Kinetic Resolution of Chiral 2-Cyclohexenones
  作者：Robert Naasz、Leggy A. Arnold、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1002/1521-3773(20010302)40:5<927::aid-anie927>3.0.co;2-k

  日期：2001.3.2

  obtained enantiomerically pure by employing the chiral copper-phosphoramidite complex [Cu(OTf)2 L*] as a highly efficient catalyst for their kinetic resolution (>99 % ee at 52 % conversion, selectivity S>200). These important building blocks can be obtained on a synthetically interesting scale, as was demonstrated by the successful multigram resolution of 5-methyl-2-cyclohexenone. Tf=trifluoromethanesulfonyl

  通过使用手性铜-亚磷酰胺络合物[Cu（OTf）2 L *]作为其动力学拆分的高效催化剂，可以得到对映体纯的多种取代的2-环己酮，如（R）-1 （> 99％ ee，转化率为52％，选择性S> 200）。这些重要的结构单元可以以合成有趣的规模获得，如成功的5-甲基-2-环己烯酮的克数解析度所证明的那样。Tf ＝三氟甲磺酰基。
• Broadening the scope of Baeyer–Villiger monooxygenase activities toward α,β-unsaturated ketones: a promising route to chiral enol-lactones and ene-lactones
  作者：T. Reignier、V. de Berardinis、J.-L. Petit、A. Mariage、K. Hamzé、K. Duquesne、V. Alphand

  DOI：10.1039/c4cc02541e

  日期：——

  Three regiodivergent Baeyer–Villiger mono-oxygenases (enantioselectively) oxidized a series of cyclic α,β-unsaturated ketones into (chiral) either enol-lactones or ene-lactones. An easy-to-use and efficient biocatalytic process based on a host-microorganism deprived of unwanted activities (knock-out mutant) was developed to enable the exclusive synthesis of unsaturated lactones.

  三种区域多样性的Baeyer–Villiger单氧化酶（对映体选择性）将一系列环状α,β-不饱和酮氧化为（手性）苯乙烯内酯或烯内酯。开发了一种基于去除不需要活性的宿主微生物（敲除突变体）的易用高效的生物催化过程，以实现不饱和内酯的专一合成。
• A reagent for cyclohexene annelation
  作者：James A. Thomas、Clayton H. Heathcock

  DOI：10.1016/s0040-4039(00)78654-0

  日期：1980.1

  Reagent 1 is a useful reagent for carrying out the annelation 2→3.

  试剂1是用于进行脱核2→3的有用试剂。