1-(2,3,5,6-tetramethyl-4-propionylphenyl)propan-1-one | 69187-01-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,5,6-tetramethyl-4-propionylphenyl)propan-1-one
• 英文别名: 1,2,4,5-tetramethyl-3,6-dipropionyl-benzene；3¹.6¹-Dioxo-1.2.4.5-tetramethyl-3.6-dipropyl-benzol；1,2,4,5-Tetramethyl-3,6-dipropionyl-benzol；eso-Dipropionyl-durol；Dipropio-durol；Dipropiodurene；1-(2,3,5,6-tetramethyl-4-propanoylphenyl)propan-1-one
• CAS: 69187-01-5
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: GPRSXUPELFMGKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-(2,3,5,6-tetramethyl-4-propionylphenyl)propan-1-one 以 苯 为溶剂， 生成 (4S,9S)-4,9-diethyl-2,7-dimethyltricyclo[6.2.0.03,6]deca-1,3(6),7-triene-4,9-diol 、 (4S,9R)-4,9-diethyl-2,7-dimethyltricyclo[6.2.0.03,6]deca-1,3(6),7-triene-4,9-diol
  参考文献：
  名称：

  Self-Assembly of Conformationally Rigid Dialcohols (Bis-Benzocyclobutenols): Supramolecular Cyclophanes and Arrays

  摘要：

  Bis-benzocyclobutenols are synthetically important intermediates, and their structures have been established for the first time. These unique molecular systems allow investigation of the hydrogen bond-mediated aggregation of diols with rigid disposition of the hydroxyl groups on both sides of a flat arene core, namely bis-benzocyclobutene. The syn-diols la and 2a were found to assemble via O-H center dot center dot center dot O hydrogen bonds between the hydroxyl groups into dimers, which may be termed "supramolecular cyclophanes". However, the analogous diols that are sterically encumbered by ethyl and phenyl groups were found to aggregate via adoption of tetrameric (syn-2c) or water-expanded dimeric (syn-2b) supramolecular synthons. The sterically un-hindered anti diols were found to self-assemble via helical supramolecular synthon in contrast to the sterically encumbered ones; the latter were found to display preference to undergo cyclic tetrameric aggregation. The results thus point to intriguing possibilities in the adoption of supramolecular synthons when a given diol is constrained by the obligation to exploit two or more functional groups of the same kind.

  DOI：

  10.1021/cg400791a
• 作为产物：
  描述：

  1,2,4,5-四甲苯 、 丙酰氯 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 生成 1-(2,3,5,6-tetramethyl-4-propionylphenyl)propan-1-one
  参考文献：
  名称：

  几种二新戊酰多甲基苯的合成

  摘要：

  2,4-二新戊酰基-1,3,5-三甲基苯、4,6-二新戊酰基-1,2,3,5-四甲基苯和 3,6-二新戊酰基-1,2,4,5-四甲基苯的制备方法如下：相应的多甲基苯的 Friedel-Grafts 二丙酰化，然后在沸腾的苯 - 叔丁醇中用叔丁醇钾和甲基碘彻底甲基化得到的二酮。报告了这些新化合物的 PMR 和 IR 光谱。

  DOI：

  10.1246/bcsj.51.3393

文献信息

• Baum; Meyer,V., Chemische Berichte, 1895, vol. 28, p. 3213
  作者：Baum、Meyer,V.

  DOI：——

  日期：——
• PINKUS A. G.; KALYANAM N., ORG. PREP. AND PROCED. INT., 1978, 10, NO 6, 255-260
  作者：PINKUS A. G.、 KALYANAM N.

  DOI：——

  日期：——
• SUZUKI HITOMI; AOMORI YASUO; MISHINA TADASHI; HANAFUSA TERUKIYO, BULL. CHEM. SOC. JAP., 1978, 51, NO 11, 3393-3394
  作者：SUZUKI HITOMI、 AOMORI YASUO、 MISHINA TADASHI、 HANAFUSA TERUKIYO

  DOI：——

  日期：——
• The Synthesis of Several Dipivaloylpolymethylbenzenes
  作者：Hitomi Suzuki、Yasuo Aomori、Tadashi Mishina、Terukiyo Hanafusa

  DOI：10.1246/bcsj.51.3393

  日期：1978.11

  6-dipivaloyl-1,2,4,5-tetramethylbenzene were prepared by the Friedel-Grafts dipropionylation of the corresponding polymethylbenzenes, followed by the exhaustive methylation of the resulting diketones with potassium t-butoxide and methyl iodide in boiling benzene-t-butyl alcohol. The PMR and IR spectra are reported for these new compounds.

  2,4-二新戊酰基-1,3,5-三甲基苯、4,6-二新戊酰基-1,2,3,5-四甲基苯和 3,6-二新戊酰基-1,2,4,5-四甲基苯的制备方法如下：相应的多甲基苯的 Friedel-Grafts 二丙酰化，然后在沸腾的苯 - 叔丁醇中用叔丁醇钾和甲基碘彻底甲基化得到的二酮。报告了这些新化合物的 PMR 和 IR 光谱。
• Self-Assembly of Conformationally Rigid Dialcohols (Bis-Benzocyclobutenols): Supramolecular Cyclophanes and Arrays
  作者：Alankriti Bajpai、Parthasarathy Venkatakrishnan、Susovan Mandal、Subhas Samanta、Paloth Venugopalan、Jarugu Narasimha Moorthy

  DOI：10.1021/cg400791a

  日期：2013.11.6

  Bis-benzocyclobutenols are synthetically important intermediates, and their structures have been established for the first time. These unique molecular systems allow investigation of the hydrogen bond-mediated aggregation of diols with rigid disposition of the hydroxyl groups on both sides of a flat arene core, namely bis-benzocyclobutene. The syn-diols la and 2a were found to assemble via O-H center dot center dot center dot O hydrogen bonds between the hydroxyl groups into dimers, which may be termed "supramolecular cyclophanes". However, the analogous diols that are sterically encumbered by ethyl and phenyl groups were found to aggregate via adoption of tetrameric (syn-2c) or water-expanded dimeric (syn-2b) supramolecular synthons. The sterically un-hindered anti diols were found to self-assemble via helical supramolecular synthon in contrast to the sterically encumbered ones; the latter were found to display preference to undergo cyclic tetrameric aggregation. The results thus point to intriguing possibilities in the adoption of supramolecular synthons when a given diol is constrained by the obligation to exploit two or more functional groups of the same kind.