2,6,6-trimethyl-3-oxo-cyclohex-1-enecarboxylic acid | 51823-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6,6-trimethyl-3-oxo-cyclohex-1-enecarboxylic acid
• 英文别名: 2,6,6-Trimethyl-3-oxo-cyclohex-1-encarbonsaeure；3-oxo-2,6,6-trimethyl-2-cyclohexen-1-carboxylic acid；2,6,6-Trimethyl-3-oxocyclohexene-1-carboxylic acid
• CAS: 51823-74-6
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: NCJFEURQKCATER-UHFFFAOYSA-N

物化性质

• 沸点：
  293.6±39.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6,6-trimethyl-3-oxo-cyclohex-1-enecarboxylic acid 生成 2,6,6-trimethyl-3-semicarbazono-cyclohex-1-enecarboxylic acid
  参考文献：
  名称：

  Wendt, Chemische Berichte, 1941, vol. 74, p. 1242,1246

  摘要：

  DOI：
• 作为产物：
  描述：

  3-hydroxy-2,6,6-trimethyl-1-cyclohexene-1-carboxylic acid 在 chromium(VI) oxide 、 硫酸 、 溶剂黄146 作用下， 生成 2,6,6-trimethyl-3-oxo-cyclohex-1-enecarboxylic acid
  参考文献：
  名称：

  Wendt, Chemische Berichte, 1941, vol. 74, p. 1242,1246

  摘要：

  DOI：

文献信息

• DL-Strigol intermediates
  申请人：Wisconsin Alumni Research Foundation

  公开号：US03954806A1

  公开（公告）日：1976-05-04

  A process for preparing dl-strigol, a potent seed germination agent, which comprises preparing the 2-bromomethyl-substituted methyl ester of 2,6,6-trimethylcyclohex-1-en-3-one-1-carboxylic acid, alkylating and cyclizing the said compound with an excess of dimethyl sodiomalonate to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-carboxylate and its enol, subjecting the said keto and enol forms of the compound, in admixture, to alkylation with methyl bromoacetate followed by acidic hydrolysis and spontaneous decarboxylation to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid, reducing the said acetic acid with a hydride reducing agent and recovering and separating the resulting 1,4-cis and trans-dihydroxy-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid lactones, formylating each of the cis and trans .gamma. lactones, alkylating the respective resulting hydroxy methylene lactones with bromobutenolide and recovering dl-strigol, dl-4'-epi-strigol, dl-4-epi-strigol and dl-4,4'-diepi-strigol. New compounds useful as intermediates in the above process are also shown.

  一种制备强效种子萌发剂dl-strigol的过程，包括制备2-溴甲基取代的2,6,6-三甲基环己-1-烯-3-酮-1-羧酸甲酯，将该化合物与过量的二甲基苏打酸甲酯烷基化和环化，得到甲基1,4-二酮-7,7-二甲基-4,5,6,7-四氢茚-2-羧酸甲酯及其烯醇，将该化合物的酮和烯醇形式混合，进行甲基溴乙酸酯烷基化，然后进行酸性水解和自发脱羧，得到甲基1,4-二酮-7,7-二甲基-4,5,6,7-四氢茚-2-乙酸，用还原剂还原该乙酸并回收和分离所得的1,4-cis和trans-二羟基-7,7-二甲基-4,5,6,7-四氢茚-2-乙酸内酯，对cis和trans .gamma.内酯进行甲酰化，用溴丁内酯烷基化各自得到的羟基亚甲基内酯，并回收dl-strigol，dl-4'-epi-strigol，dl-4-epi-strigol和dl-4,4'-diepi-strigol。还显示了在上述过程中有用的新化合物中间体。
• Dl-strigol intermediate
  申请人：Wisconsin Alumni Research Foundation

  公开号：US03972916A1

  公开（公告）日：1976-08-03

  A process for preparing dl-strigol, a potent seed germination agent, which comprises preparing the 2-bromomethyl-substituted methyl ester of 2,6,6-trimethylcyclohex-1-en-3-one-1-carboxylic acid, alkylating and cyclizing the said compound with an excess of dimethyl sodiomalonate to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-carboxylate and its enol, subjecting the said keto and enol forms of the compound, in admixture, to alkylation with methyl bromoacetate followed by acidic hydrolysis and spontaneous decarboxylation to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid, reducing the said acetic with a hydride reducing agent and recovering and separating the resulting 1,4-cis and trans-dihydroxy-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid lactones, formylating each of the cis and trans .gamma. lactones, alkylating the respective resulting hydroxy methylene lactones with bromobutenolide and recovering dl-strigol, dl-4'-epi-strigol, dl-4-epi-strigol and dl-4,4'-diepi-strigol. New compounds useful as intermediates in the above process are also shown.

  一种制备强效种子萌发剂dl-strigol的方法，包括制备2-溴甲基取代的2,6,6-三甲基环己-1-烯-3-酮-1-羧酸甲酯，用过量的二甲基丙烯酸钠酯烷基化和环化所述化合物以获得甲基1,4-二酮-7,7-二甲基-4,5,6,7-四氢茚-2-羧酸甲酯及其烯醇形式，将所述化合物的酮和烯醇形式混合物进行烷基化，随后进行酸性水解和自发脱羧以获得甲基1,4-二酮-7,7-二甲基-4,5,6,7-四氢茚-2-乙酸，用还原剂还原所述乙酸，并回收和分离所得的1,4-顺式和反式-二羟基-7,7-二甲基-4,5,6,7-四氢茚-2-乙酸内酯，对顺式和反式γ内酯进行甲酰化，用溴丁内酯烷基化各自所得的羟甲基内酯，并回收dl-strigol、dl-4'-epi-strigol、dl-4-epi-strigol和dl-4,4'-diepi-strigol。还展示了在上述过程中有用的新化合物中间体。
• Practical total synthesis of (.+-.)-strigol
  作者：Dee W. Brooks、H. S. Bevinakatti、Eileen Kennedy、Jim Hathaway

  DOI：10.1021/jo00205a014

  日期：1985.3
• Le γ-Pyronène : Synthon d'Accès au Safranal et Précurseur d'Intermédiaires de Synthèse de la Forskoline et du Strigol
  作者：B. Boulin、B. Arreguy-San Miguel、B. Delmond

  DOI：10.1016/s0040-4020(98)83010-x

  日期：1998.3

  gamma-Pyronene, a terpenic synthon available from myrcene, is an excellent raw material for the preparation of numerous intermediates used in the synthesis of perfumes, retinoids and biological derivatives such as forskolin or strigol. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Improved yield preparation of 3-oxo-2,6,6-trimethylcyclohex-1-ene-1-carboxylic acid, an important intermediate in the synthesis of (.+-.)-strigol
  作者：Armand B. Pepperman

  DOI：10.1021/jo00337a056

  日期：1981.11