2-ethylcyclohexane-1,3-dione | 18456-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethylcyclohexane-1,3-dione
• 英文别名: 2-ethyl-1,3-cyclohexanedione；2-Ethyl-1,3-cyclohexandion；2-Ethyl-cyclohexandion-(1,3)
• CAS: 18456-78-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: CBYSZLTXXOKQQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethylcyclohexane-1,3-dione 在 barium dihydroxide 作用下， 生成 5-氧代-辛酸
  参考文献：
  名称：

  Stetter; Dierichs, Chemische Berichte, 1952, vol. 85, p. 61,71

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2,2-dimethylhydrazino)cyclohex-2-en-1-one 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 2-ethylcyclohexane-1,3-dione
  参考文献：
  名称：

  Regioselective Alkylations of Cyclic 1,3-Diketonesvia Metalated Dimethylhydrazones

  摘要：

  Cyclic 1,3- diketones 1 are transformed into their 2,2-dimethylhydrazones 2, which can be alkylated regioselectively at different positions after mono-, di-, tri-, and tetrametalation. Monometalated C-2 unsubstituted hydrazones afford C-2 and N-alkylation, monometalated C-2 substituted hydrazones afford only C-2 alkylation. The regioselectivity of the alkylation of the polymetalated hydrazones follows Hauser's rule according to the sequence: NH- > C-4 Ha > C-5 > C-4 Hb. Hydrolysis of the product hydrazones 3-5 afforded mono-and polyalkylated 1,3- diketones 7 in good yields.

  DOI：

  10.1002/prac.19973390199

文献信息

• Synthesis of 13-alkyl-gon-4-ones
  申请人：Smith; Herchel

  公开号：US03959322A1

  公开（公告）日：1976-05-25

  The preparation of 13-methylgon-4-enes and novel 13-polycarbonalkylgon-4-enes by a new total synthesis is described. 13-Alkylgon-4-enes having progestational, anabolic and androgenic activities are prepared by forming a tetracylic gonane structure unsaturated in the 1,3,5(10),9(11) and 14-positions, selectively reducing in the B- and C-rings, and converting the aromatic A-ring compounds so-produced to gon-4-enes by Birch reduction and hydrolysis.

  描述了通过新的全合成方法制备13-甲基孕-4-烯和新型13-聚碳烷基孕-4-烯。通过形成在1,3,5(10),9(11)和14-位置不饱和的四环孕烷结构，选择性地在B和C环中还原，并将所产生的芳香A环化合物转化为孕-4-烯，制备具有孕激素、合成激素和雄激素活性的13-烷基孕-4-烯。
• Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C₆F₅)₃, <i>N</i>-Alkylamine and a Zn-Based Catalyst
  作者：Min Cao、Ahmet Yesilcimen、Masayuki Wasa

  DOI：10.1021/jacs.8b13757

  日期：2019.3.13

  An efficient and highly enantioselective Conia-ene-type process has been developed. Reactions are catalyzed by a combination of B(C6F5)3, an N-alkylamine and a BOX-ZnI2 complex. Specifically, through cooperative action of B(C6F5)3 and amine, ketones with poorly acidic α-C-H bonds can be converted in situ to the corresponding enolates. Subsequent enantioselective cyclization involving a BOX-ZnI2-activated

  已开发出一种高效且高度对映选择性的 Conia-ene 型工艺。反应由 B(C6F5)3、N-烷基胺和 BOX-ZnI2 复合物的组合催化。具体而言，通过 B(C6F5)3 和胺的协同作用，具有弱酸性 α-CH 键的酮可以原位转化为相应的烯醇化物。随后涉及 BOX-ZnI2 活化炔烃的对映选择性环化导致各种环戊烯的形成，产率高达 99% 和 99:1。
• Synthesis of gon-4-enes
  申请人：Smith; Herchel

  公开号：US04002746A1

  公开（公告）日：1977-01-11

  1. A therapeutic composition having progestational activity comprising as active ingredient a 17-aliphatic carboxylic acid ester of 17.alpha.-ethynyl-18-methyl-19-nortestosterone and a pharmaceutical carrier for said compound.

  一种具有孕激素活性的治疗组合物，其活性成分为17-脂肪族羧酸酯的17α-乙炔基-18-甲基-19-去甲睾酮，以及用于该化合物的药用载体。
• Organocatalytic Sequential One-Pot Double Cascade Asymmetric Synthesis of Wieland−Miescher Ketone Analogues from a Knoevenagel/Hydrogenation/Robinson Annulation Sequence:  Scope and Applications of Organocatalytic Biomimetic Reductions
  作者：Dhevalapally B. Ramachary、Mamillapalli Kishor

  DOI：10.1021/jo070277i

  日期：2007.7.1

  practical and novel organocatalytic chemo- and enantioselective process for the cascade synthesis of highly substituted 2-alkyl-cyclohexane-1,3-diones and Wieland−Miescher (W−M) ketone analogs is presented via reductive alkylation as a key step. First time, we developed the one-step alkylation of dimedone and 1,3-cyclohexanedione with aldehydes and Hantzsch ester through an organocatalytic reductive alkylation

  通过还原烷基化，提出了一种实用且新颖的有机催化化学和对映选择性工艺，用于级联合成高度取代的2-烷基-环己烷-1,3-二酮和Wieland-Miescher（WM）酮类似物，这是关键步骤。首次，我们通过有机催化还原烷基化策略开发了二醛和1,3-环己二酮与醛和Hantzsch酯的一步烷基化。l的直接组合CH酸（二甲酮和1,3-环己烷二酮），醛，汉茨sch酯和甲基乙烯基酮的脯氨酸催化的级联Knoevenagel /加氢和级联的Robinson环氧化反应提供了高官能度的W-M酮类似物，并具有良好的收率。优异的对映选择性。许多还原性烷基化产物直接显示在药物化学中。
• Catalytic 1,2-Rearrangements: Organocatalyzed Michael/Semi-Pinacol-like Rearrangement Cascade of 1,3-Diones and Nitroolefins
  作者：Tsung-Jung Jao、Pavan Sudheer Akula、Bor-Cherng Hong、Gene-Hsiang Lee

  DOI：10.1021/acs.orglett.9b03912

  日期：2020.1.3

  New types of organocatalytic 1,2-rearrangements, which resemble the Smiles-like or semi-pinacol-like rearrangement, of Michael adducts of 1,3-dicarbonyl-2-alkyl compounds and nitroalkenes have been realized. Unlike the well-known conjugate addition, the reaction affords the 1-phenyl-1-nitroalkanes via unprecedented rearrangement and cascade reactions. Structures of the appropriate products were unambiguously

  已经实现了新型的类似于1,3-二羰基-2-烷基化合物和硝基烯烃的迈克尔加成物的类似于Smiles或半频哪醇的重排的有机催化1,2-重排。与众所周知的共轭加成不同，该反应通过空前的重排和级联反应提供了1-苯基-1-硝基烷烃。适当产物的结构通过X射线晶体学明确表征。