1,2-dimethyl-1-cyclohexen-4-one | 33475-09-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-dimethyl-1-cyclohexen-4-one
• 英文别名: 3,4-dimethyl-3-cyclohexen-1-one；3,4-dimethyl-3-cyclohexenone；3,4-dimethylcyclohex-3-enone；1,2-Dimethyl-1-cyclohexen-4-on；3,4-Dimethyl-cyclohex-3-enon；3,4 Dimethylcyclohexen-3-on；3,4-Dimethylcyclohex-3-en-1-one
• CAS: 33475-09-1
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: WBZQYNKJZBACLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1,2-dimethyl-1-cyclohexen-4-one 在 五氟化锑 作用下， 以 氢氟酸 为溶剂， 反应 2.0h， 生成 3-异丙基-2-环戊烯-1-酮
  参考文献：
  名称：

  Jacquesy,R.; Patoiseau,J.-F., Bulletin de la Societe Chimique de France, 1978, vol. , p. 255 - 262

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methoxy-4,5-dimethylcyclohexa-1,4-diene 以30.0 g的产率得到1,2-dimethyl-1-cyclohexen-4-one
  参考文献：
  名称：

  Factors influencing conformational preferences in cyclohexenes

  摘要：

  DOI：

  10.1021/ja00312a030

文献信息

• 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。
• Reaction of Enamines with Acetals or Trialkyl Orthoformates Activated by Lewis Acids
  作者：Osamu Takazawa、Kunio Kogami、Kazuo Hayashi

  DOI：10.1246/bcsj.57.1876

  日期：1984.7

  Enamines, prepared readily from various carbonyl compounds, react with acetals or trialkyl orthoformates in the presence of Lewis acids such as BF3·OEt2 to give corresponding β-alkoxy carbonyl compounds or α-dialkoxymethyl carbonyl compounds in good yields. The reaction of dienamines with acetals or trialkyl orthoformates also selectively gives corresponding β,γ-unsaturated α-(α-alkoxyalkyl) carbonyl compounds

  烯胺很容易由各种羰基化合物制备，在路易斯酸（如 BF3·OEt2）存在下与缩醛或原甲酸三烷基酯反应，以良好的收率得到相应的 β-烷氧基羰基化合物或 α-二烷氧基甲基羰基化合物。二烯胺与缩醛或原甲酸三烷基酯的反应也选择性地以良好的产率得到相应的β,γ-不饱和α-(α-烷氧基烷基)羰基化合物或β,γ-不饱和α-二烷氧基甲基羰基化合物。
• Oxidative desulfonylation. Phenyl vinyl sulfone as a ketene synthetic equivalent
  作者：R.Daniel Little、Sun Ok Myong

  DOI：10.1016/s0040-4039(00)78683-7

  日期：1980.1

  α-Sulfonyl carbanions undergo oxidative desulfonylation to form ketones upon treatment with molybdenum peroxide MoO5·Py·HMPA (MoOPH) in THF at −78°C.

  在-78°C下用过氧化钼MoO 5 ·Py·HMPA（MoOPH）在THF中处理后，α-磺酰基碳负离子进行氧化脱磺酰化反应生成酮。
• Glucocorticoid receptor modulators
  申请人：Dow L. Robert

  公开号：US20070117805A1

  公开（公告）日：2007-05-24

  The present invention provides non-steroidal compounds of formula I which are selective modulators (i.e., agonists and antagonists) of a steroid receptor, specifically, the glucocorticoid receptor. The present invention also provides pharmaceutical compositions containing these compounds and methods for using these compounds to treat animals requiring glucocorticoid receptor agonist or antagonist therapy. Glucocorticoid receptor modulators are useful to the diseases, such as obesity, diabetes, inflammation and others as described below. The present invention also provides intermediates and processes for preparing these compounds.

  本发明提供公式I的非甾体化合物，它们是类固醇受体的选择性调节剂（即激动剂和拮抗剂），具体地，是糖皮质激素受体。本发明还提供含有这些化合物的药物组合物，并使用这些化合物治疗需要糖皮质激素受体激动剂或拮抗剂治疗的动物的方法。糖皮质激素受体调节剂对于肥胖症、糖尿病、炎症等疾病是有用的，如下所述。本发明还提供制备这些化合物的中间体和方法。
• Cycloaddition Reactions of 1-Phenylseleno-2-(<i>p</i>-toluenesulfonyl)ethyne
  作者：Thomas G. Back、Richard J. Bethell、Masood Parvez、Jerry A. Taylor、Daniel Wehrli

  DOI：10.1021/jo990730t

  日期：1999.10.1

  1-Phenylseleno-2-(p-toluenesulfonyl)ethyne (1) is an effective dienophile and dipolarophile. It underwent facile Diels-Alder reactions with a variety of dienes to afford vicinal sulfone- and selenide-functionalized 1,4-cyclohexadienes. Unexpected regiochemistry that is the opposite of what is obtained with simple acetylenic sulfones was observed with several unsymmetrical dienes containing methyl or methoxy substituents at the 1- or 2-position. Acetylene 1 reacted with (trimethylsilyl)methyl azide, diazomethane, and 2,4,6-trimethylbenzonitrile N-oxide via 1,3-dipolar cycloadditions to afford the corresponding triazole, 1,2-diazole, and isoxazole products. It also underwent an ene reaction with beta-pinene that showed anomalous regiochemistry compared to other acetylenic sulfones. The Diels-Alder cycloadducts obtained from the reaction of 1 with 2,3-dimethyl-1,3,butadiene and 1,3-cyclohexadiene were readily converted into the corresponding beta-keto sulfones and ketones, thus rendering 1 as the synthetic equivalent of p-toluenesulfonylketene and ketene, respectively. Base-catalyzed elimination of TsOH from the Diels-Alder cycloadduct obtained with 2,3-dimethyl-1,3-butadiene afforded the corresponding aryl phenyl selenide, while the adduct from piperylene underwent oxidation to its selenoxide, followed by a Pummerer-type reaction to produce 2-(phenylseleno)-3-(p-toluenesulfonyl)toluene. The reaction of the bicyclic Diels-Alder product obtained from 1,3-cyclohexadiene with MeCu(SePh)Li resulted in substitution of the phenylseleno moiety by a methyl group, whereas similar treatment, of the monocyclic adduct derived from piperylene effected elimination of PhSeH and aromatization.

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