Methyl-1.4-dioxo-7.7-dimethyl-4.5.6.7-tetrahydroindan-2-carboxylat | 51799-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-1.4-dioxo-7.7-dimethyl-4.5.6.7-tetrahydroindan-2-carboxylat
• 英文别名: 7,7-Dimethyl-1,4-dioxo-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid methyl ester；methyl 4,4-dimethyl-3,7-dioxo-1,2,5,6-tetrahydroindene-2-carboxylate
• CAS: 51799-98-5
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: BJCRCXKQFAXVNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  136-138 °C
• 沸点：
  357.3±41.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl-1.4-dioxo-7.7-dimethyl-4.5.6.7-tetrahydroindan-2-carboxylat 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 56.0h， 生成 (+/-)-(3aR*,5S*,8bS*)-5-hydroxy-8,8-dimethyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one
  参考文献：
  名称：

  Practical total synthesis of (.+-.)-strigol

  摘要：

  DOI：

  10.1021/jo00205a014
• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 chromium(VI) oxide 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 甲酸 、 硫酸 、 sodium methylate 、 potassium carbonate 、 间氯过氧苯甲酸 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 丙酮 为溶剂， 反应 46.33h， 生成 Methyl-1.4-dioxo-7.7-dimethyl-4.5.6.7-tetrahydroindan-2-carboxylat
  参考文献：
  名称：

  IMPROVED SYNTHESIS OF 7,7-DIMETHYL-1,4-DIOXO-2,3,4,5,6,7-HEXAHYDROINDEN-2-YL-ACETIC AND PROPIONIC ACID FROM CITRAL

  摘要：

  DOI：

  10.1080/00304949809355262

文献信息

• Synthesis and biological evaluation of A-ring analogs of the natural germination stimulant strigol
  作者：E. M. Mangnus、B. Zwanenburg

  DOI：10.1002/recl.19921110308

  日期：——

  An A-ring-derived analog of the natural germination stimulant, Strigol (1), has been prepared from citral in an unambiguous manner. This analog, 2, a γ-hydroxy aldehyde for which a high stimulant activity was claimed in the literature, has been re-evaluated as a germination stimulant for seeds of parasitic weeds and was found to be inactive. It was also shown that analog 2 is rather stable in aqueous

  从柠檬醛以明确的方式制备了自然萌发兴奋剂的A环衍生类似物Strigol（1）。该类似物2，一种在文献中声称具有高刺激活性的γ-羟基醛，已经被重新评估为寄生杂草种子的发芽刺激剂，并且被发现没有活性。与其他报道相比，还显示类似物2在水溶液中相当稳定。
• 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。
• Convenient synthesis of a hydrindan precursor to strigol
  作者：Lloyd J. Dolby、Gunnar Hanson

  DOI：10.1021/jo00865a036

  日期：1976.2
• SAMSON, E.;FRISCHMUTH, K.;BERLAGE, U.;HEINZ, U.;HOBERT, K.;WELZEL, P., TETRAHEDRON, 47,(1991) N, C. 1411-1416
  作者：SAMSON, E.、FRISCHMUTH, K.、BERLAGE, U.、HEINZ, U.、HOBERT, K.、WELZEL, P.

  DOI：——

  日期：——