3-Methyl-4-isopropyl-2-cyclohexen-1-one | 24826-71-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-Methyl-4-isopropyl-2-cyclohexen-1-one
• 英文别名: 3-methyl-4-isopropyl-cyclohex-2-enone；o-Menthenon；1-Methyl-6-isopropylcyclohex-1-en-3-on；3-methyl-4-propan-2-ylcyclohex-2-en-1-one
• CAS: 24826-71-9
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: PICMFKWTWAPKCB-UHFFFAOYSA-N

物化性质

• 沸点：
  224.5±10.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  甲基碘化镁 、 3-Methyl-4-isopropyl-2-cyclohexen-1-one 在 copper diacetate 作用下， 生成 4-Isopropyl-3,3-dimethyl-cyclohexanone
  参考文献：
  名称：

  桥接环系统。第十五部分。新丁烯（2,6,8,8-四甲基三环[5,2,2,0 1,6 ]十一碳-2-烯）的结构

  摘要：

  一种新的石竹烯重排产物新丁香（4）的结构解析表明，它是2,6,8,8-四甲基三环[5,2,2,0 1,6 ]十一碳-2-烯，并显示了立体化学。

  DOI：

  10.1039/j39690002634
• 作为产物：
  描述：

  2-乙酰基-2-异丙基-5-氧代己酸甲酯 在 哌啶 、 2,3,4-三甲基吡啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 18.0h， 生成 3-Methyl-4-isopropyl-2-cyclohexen-1-one
  参考文献：
  名称：

  贝姆·阿尔道·林施吕斯（Zimregioselektivitätbeim Aldol-ringschluss）

  摘要：

  根据反应条件适当选择，我在达到1,5-二酮类的区域选择性环闭合，要么II或III。该定向醛醇缩合成功地用于单萜哌啶酮的短合成。

  DOI：

  10.1016/0040-4039(81)80117-7

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。
• Asymmetric Approach toward Chiral Cyclohex-2-enones from Anisoles via an Enantioselective Isomerization by a New Chiral Diamine Catalyst
  作者：Jung Hwa Lee、Li Deng

  DOI：10.1021/ja308623n

  日期：2012.11.7

  A 3-step asymmetric approach toward the optically active chiral cyclohex-2-enones from anisoles has been developed. The crucial asymmetric induction step is an unprecedented catalytic enantioselective isomerization of β,γ-unsaturated cyclohex-3-en-1-ones to the corresponding α,β-unsaturated chiral enones. This new asymmetric transformation was realized by cooperative iminium-base catalysis with an

  开发了一种从苯甲醚制备光学活性手性环己-2-烯酮的三步不对称方法。关键的不对称诱导步骤是β,γ-不饱和环己-3-en-1-酮前所未有的催化对映选择性异构化为相应的α,β-不饱和手性烯酮。这种新的不对称转化是通过亚胺基催化与电子可调的新型有机催化剂的协同实现的。(-)-异棘花醛的对映选择性全合成凸显了该方法的合成效用。
• Lewis acid induced conjugate addition of alkenes to .alpha.,.beta.-unsaturated ketones or aldehydes
  作者：Barry B. Snider、David J. Rodini、Jan Van Straten

  DOI：10.1021/ja00538a028

  日期：1980.8
• New approaches to the synthesis of alkyl-substituted enol lactone systems, inhibitors of the serine protease elastase
  作者：Wei Dai、John A. Katzenellenbogen

  DOI：10.1021/jo00059a049

  日期：1993.3

  We have synthesized a series of alkyl-substituted enol lactones designed to act as mechanism-based inhibitors of human neutrophil elastase (HLE). General methods were developed for the preparation of alpha- and beta-alkyl-substituted 5-hexynoic acids by the bromoform reaction on the corresponding alkynoic methyl ketone, prepared by an Eschenmoser-Tanabe fragmentation sequence from a suitably substituted cyclohexenone. By this method, beta-methyl- and beta,beta-dimethyl-5-hexynoic acids were synthesized from commercially available isophorone and 3,5-dimethyl-2-cyclohexen-1-one, respectively. Alpha-Substituted 5-hexynoic acids were prepared from 3-ethoxy-2-cyclohexen-1-one, using a novel ZnCl2-mediated alkylation that we developed; this method gives high yields of alpha'-alkylation products, even with secondary halides. The most efficient method for the preparation of alpha-substituted 5-hexynoic acids involved a four-reaction sequence-alkylation of the alpha-substituted ester with 1,4-dibromobutane, elimination, bromination and bisdehydrobromination-that proceeded in high overall yield. Protio enol lactonizations were performed with mercury(II) catalysis in CH2Cl2 or CH2Cl2-H2O. Stereo-selective Z-bromo enol lactonization was carried out by Br+-induced lactonization in the presence of Ag+. E-Bromo enol lactonization with N-bromosuccinimide in CH2Cl2 in the presence of a small amount of water gave better yields and shorter reaction times than the traditional anhydrous conditions. In studies of the inhibitory activity of these lactones toward several proteases (reported in full elsewhere), we found that the alpha-alkyl-substituted protio and bromo enol lactones 1-3 were very good inhibitors of HLE, with k(a)/K(i) values ranging from 14 500 to 37 500 M-1 s-1; the beta-alkyl-substituted enol lactones 5-8 showed only moderate inhibition of HLE.
• SNIDER B. B.; RODINI D. J.; STRATEN J. VAN, J. AMER. CHEM. SOC., 1980, 102, NO 18, 5872-5880
  作者：SNIDER B. B.、 RODINI D. J.、 STRATEN J. VAN

  DOI：——

  日期：——