3-乙基-5,5-二甲基环己-2-烯-1-酮 | 28017-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙基-5,5-二甲基环己-2-烯-1-酮
• 英文名称: 3-Aethyl-5,5-dimethyl-2-cyclohexen-1-on
• 英文别名: 3-ethyl-5,5-dimethylcyclohex-2-en-1-one；3-ethyl-5,5-dimethylcyclohex-2-enone；5,5-dimethyl-3-ethylcyclohexenone；3-ethyl-5,5-dimethyl-cyclohex-2-enone；3-Aethyl-5,5-dimethyl-cyclohex-2-enon；5,5-Dimethyl-3-ethyl-cyclohexen-(2)-on
• CAS: 28017-78-9
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: BHWWOYJEWQVANZ-UHFFFAOYSA-N

物化性质

• 沸点：
  105-106 °C(Press: 5 Torr)
• 密度：
  0.894±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：

  3-乙基-5,5-二甲基环己-2-烯-1-酮 在 palladium on activated charcoal potassium tert-butylate 、 氨 、 氢气 、 lithium 、 pyridinium chlorochromate 作用下， 以 甲醇 、 苯 为溶剂， -33.0 ℃ 、303.98 kPa 条件下， 反应 18.0h， 生成 (1S,5R,8S,11R)-3,3,7,11-tetramethyltricyclo[6.3.0.01,5]undecan-6-one
  参考文献：
  名称：

  Spiroannulation approach to pentalenene, an angular triquinane sesquiterpene

  摘要：

  The route to the angular triquinane (+/-)-pentalenene (la) followed from an efficient geminal acylation of the acetal of isophorone or its homolog 6b by 1,2-bis((trimethylsilyl) oxy) cyclobutene (3) in the presence of boron trifluoride etherate. Ring cleavage and reclosure (9 --> 11) secured the required spiro[4.4]nonane system with a pendant ketone function in place for the closure of the final, central : I ring. The relative stereochemistry at C-9 was established during hydrogenation over palladium of the C-3 double bond of 11, but the facial selectivity was determined by the mode of reduction of the conjugated, orthogonal double bond at C-6 of 11. After cyclization to the enone 17b, the synthesis was completed by reductions of both the double bond and the ketone and simple dehydration. The 9-epi isomer (26) of (+/-)-pentalenene was synthesized also.

  DOI：

  10.1021/jo00080a018
• 作为产物：
  描述：

  2-(3-ethoxy-5,5-dimethyl-cyclohex-2-enylidene)-propionitrile 在 盐酸 作用下， 生成 3-乙基-5,5-二甲基环己-2-烯-1-酮
  参考文献：
  名称：

  Crossley; Gilling, Journal of the Chemical Society, 1910, vol. 97, p. 528

  摘要：

  DOI：

文献信息

• Iron Catalyzed Highly Enantioselective Epoxidation of Cyclic Aliphatic Enones with Aqueous H₂O₂
  作者：Olaf Cussó、Marco Cianfanelli、Xavi Ribas、Robertus J. M. Klein Gebbink、Miquel Costas

  DOI：10.1021/jacs.5b12681

  日期：2016.3.2

  An iron complex with a C1-symmetric tetradentate N-based ligand catalyzes the asymmetric epoxidation of cyclic enones and cyclohexene ketones with aqueous hydrogen peroxide, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee), under mild conditions and in short reaction times. Evidence is provided that reactions involve an electrophilic

  具有 C1 对称四齿 N 基配体的铁配合物催化环烯酮和环己烯酮与过氧化氢水溶液的不对称环氧化反应，提供相应的环氧化物，产率和对映选择性都很好（高达 99% 和 95% ee )，条件温和，反应时间短。有证据表明反应涉及亲电氧化剂，并且该元素用于对包含两个烯烃位点的烯酮进行位点选择性环氧化。
• Central nervous system active compounds. III. The synthesis of 4- and 6-substituted caprolactam derivatives by the Schmidt and Beckmann rearrangements
  作者：GI Hutchison、RH Prager、AD Ward

  DOI：10.1071/ch9802477

  日期：——

  The synthesis is described of hexahydroazepin-2-ones (caprolactams) bearing 1-4 alkyl or aryl groups at C4 and C6 by the Beckmann or Schmidt reactions on the corresponding cyclohex-2-enone. Further evidence for the mechanism of the Beckmann rearrangement of these unsaturated oximes is advanced. The central nervous system activity of the alkylated caprolactams is reported.

  介绍了以下六氢氮杂卓-2-酮（己内酰胺）的合成 在 C4 和 C6 上带有 1-4 个烷基或芳基的六氢氮杂卓-2-酮（己内酰胺）。 和 C6 上带有 1-4 个烷基或芳基的六氢氮杂卓-2-酮（己内酰胺）的合成。 环己-2-烯酮。关于这些不饱和环己-2-烯酮的贝克曼 这些不饱和肟的重排机理的进一步证据。中枢神经系统 报告了烷基化己内酰胺的中枢神经系统活性。
• Photochemische Reaktionen 119. Mitteilung [1] Zur Photospaltung konjugierter ?,?-Epoxyenone. UV.-Bestrahlung von 3-(1?,2?-Epoxy-2?-methyl-prop-1?-yl)-5,5-dimethyl-2-cyclohexen-1-on
  作者：Guy De Weck、Hans Richard Wolf

  DOI：10.1002/hlca.19810640124

  日期：1981.2.4

  Photocleavage of Conjugated π,π-Epoxyenones. UV.-Irradiation of 3-(1′,2′-Epoxy-2′-methyl-prop-1′-yl)-5,5-dimethyl-2-cyclohexene-1-one

  共轭π，π-环氧烯酮的光解。3-（1'，2'-环氧-2'-甲基-丙-1'-基）-5,5-二甲基-2-环己烯-1-酮的紫外线照射
• Remote Control of Axial Chirality: Aminocatalytic Desymmetrization of <i>N</i>-Arylmaleimides via Vinylogous Michael Addition
  作者：Nicola Di Iorio、Paolo Righi、Andrea Mazzanti、Michele Mancinelli、Alessia Ciogli、Giorgio Bencivenni

  DOI：10.1021/ja505610k

  日期：2014.7.23

  Remote control of the axial chirality of N-(2-t-butylphenyl)succinimides was realized via the vinylogous Michael addition of 3-substituted cyclohexenones to N-(2-t-butylphenyl)maleimides. 9-Amino(9-deoxy)epi-quinine promoted the enantioselective desymmetrization, leading to atropisomeric succinimides with two adjacent stereocenters.

  N-(2-t-丁基苯基)琥珀酰亚胺的轴向手性的远程控制是通过3-取代的环己烯酮与N-(2-t-丁基苯基)马来酰亚胺的乙烯基迈克尔加成实现的。9-氨基（9-脱氧）表奎宁促进对映选择性去对称化，导致具有两个相邻立体中心的阻转异构琥珀酰亚胺。
• Acid catalysis of the photochemical deconjugation reaction of 3-alkyl-2-cyclohexenones
  作者：Andreas Rudolph、Alan C. Weedon

  DOI：10.1021/ja00205a048

  日期：1989.11

  Deconjugaison photochimique de l'isophorone (trimethyl-3,5,5 cyclohexene-2 one) en dimethyl-3,3 methylene-5 cyclohexanone

  Deconjugaison photochimique de l'isophorone (trimethyl-3,5,5 cyclohexene-2 one) en 二甲基-3,3 亚甲基-5 环己酮