3,6-bis(tert-butyl)acetophenone | 2040-08-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-bis(tert-butyl)acetophenone
• 英文别名: 2,5-di-tert-butylacetophenone；2,5-bis(tert-butyl)acetophenone；2-Acetyl-1,4-di-tert-butyl-benzol；1-(2,5-Ditert-butylphenyl)ethanone
• CAS: 2040-08-6
• 化学式: C₁₆H₂₄O
• 分子量: 232.366
• InChiKey: DNMFJAQNZXOULJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3,6-bis(tert-butyl)acetophenone 、 对甲酰基苯甲酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 4-[(E)-3-(2,5-Di-tert-butyl-phenyl)-3-oxo-propenyl]-benzoic acid
  参考文献：
  名称：

  Retinobenzoic acids. 2. Structure-activity relationships of chalcone-4-carboxylic acids and flavone-4'-carboxylic acids

  摘要：

  The structure-activity relationships of (E)-chalcone-4-carboxylic acids, which are retinoidal benzoic acids represented by R-Ph-X-Ph-COOH (4, X = -COCH = CH-), are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The activity was increased by the substitution of a bulky alkyl group(s) (R), and among such compounds, (E)-4-[3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl]benzoic acid (Ch55) and (E)-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1 -propenyl]benzoic acid (Ch80) are several times more active than retinoic acid. Though the stable conformer of chalcone derivatives is linear (s-cis form), the conformationally restricted analogue 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphtho[2,3-b]py ran-2-yl)benzoic acid (Fv80) is more active than Ch80. While the effect of introduction of an oxygen atom varied, 4-[1-hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2 - naphthalenyl)-1-propenyl]benzoic acid (Re80), regarded as a derivative of Ch80 with two additional hydroxyl groups, has very strong activity.

  DOI：

  10.1021/jm00124a016
• 作为产物：
  描述：

  2,5-di-tert-butylthiophene S-oxide 以 二苯醚 、 氯仿 为溶剂， 反应 13.0h， 生成 3,6-bis(tert-butyl)acetophenone
  参考文献：
  名称：

  [4+2]-位阻噻吩S-氧化物与烯烃的环加成和环加合物的SO挤出反应

  摘要：

  图形摘要摘要描述了2,5-二-叔丁基噻吩S-氧化物和2,3,4,5-四(对甲苯基)噻吩S-氧化物与烯烃的环加成反应。将 2,5-二叔丁基噻吩 S-氧化物在 Diels-Alder 反应中作为二烯的反应性与 2,5-二-叔丁基噻吩 S,S-二氧化物进行比较。举例说明了在形成高度取代的芳族化合物的情况下环加合物的热和光化学 SO 挤出反应。

  DOI：

  10.1080/10426507.2015.1100191

文献信息

• Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity
  作者：Hiroyuki Kagechika、Emiko Kawachi、Yuichi Hashimoto、Koichi Shudo、Toshiyuki Himi

  DOI：10.1021/jm00119a021

  日期：1988.11

  a medium-sized alkyl group (isopropyl, tert-butyl, etc.) at the meta position and a carboxyl group at the para position of the other benzene ring. The bonding of the amide structure can be reversed, this moiety apparently having the role of locating the two benzene rings at suitable positions with respect to each other. Substitution at the ring position ortho to the amide group or N-methylation of the

  已显示两种类型的芳族酰胺，对苯二甲酸单苯胺和（芳基甲酰胺基）苯甲酸具有有效的类维生素A活性，可以归类为类维生素A。基于对人早幼粒细胞白血病细胞HL-60的分化诱导活性，讨论了这些酰胺的构效关系。在通式4（X ＝ NHCO或CONH）中，引起类视色素活性的必要因素是在其间位的中等尺寸烷基（异丙基，叔丁基等）和在其对位的羧基。另一个苯环。酰胺结构的键可以颠倒，该部分显然具有将两个苯环相对于彼此定位在适当位置的作用。推测是由于所得的构象变化，在酰胺基邻位的环位置取代或酰胺基的N-甲基化导致活性降低。显然，苄基甲基和羧基的相互取向以及它们之间的距离是决定类视色素活性的必要因素。在合成的化合物中，4-[（（5,6,7,8-四氢-5,5,8,8-四甲基-2-萘基）氨基甲酰基]苯甲酸（Am80）和4-[（5,6，在该测定中，7,8-四氢-5,5,8,8-四甲基-2-萘基[羧酰胺基]苯甲酸（Am580）的
• Retinobenzoic acids. 2. Structure-activity relationships of chalcone-4-carboxylic acids and flavone-4'-carboxylic acids
  作者：Hiroyuki Kagechika、Emiko Kawachi、Yuichi Hashimoto、Koichi Shudo

  DOI：10.1021/jm00124a016

  日期：1989.4

  The structure-activity relationships of (E)-chalcone-4-carboxylic acids, which are retinoidal benzoic acids represented by R-Ph-X-Ph-COOH (4, X = -COCH = CH-), are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The activity was increased by the substitution of a bulky alkyl group(s) (R), and among such compounds, (E)-4-[3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl]benzoic acid (Ch55) and (E)-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1 -propenyl]benzoic acid (Ch80) are several times more active than retinoic acid. Though the stable conformer of chalcone derivatives is linear (s-cis form), the conformationally restricted analogue 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphtho[2,3-b]py ran-2-yl)benzoic acid (Fv80) is more active than Ch80. While the effect of introduction of an oxygen atom varied, 4-[1-hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2 - naphthalenyl)-1-propenyl]benzoic acid (Re80), regarded as a derivative of Ch80 with two additional hydroxyl groups, has very strong activity.
• [4+2]-Cycloaddition of sterically hindered thiophene S-oxides to alkenes and SO extrusion reactions of the cycloadducts
  作者：Thies Thiemann、Jesus Iniesta、David J. Walton

  DOI：10.1080/10426507.2015.1100191

  日期：2016.6.2

  GRAPHICAL ABSTRACT ABSTRACT Cycloaddition reactions of 2,5-di-tert-butylthiophene S-oxide and 2,3,4,5-tetrakis(p-tolyl)thiophene S-oxide with alkenes are described. The reactivity of 2,5-di-tert-butylthiophene S-oxide as diene in Diels–Alder reactions is compared with 2,5-di-tert-butylthiophene S,S-dioxide. The thermal and photochemical SO extrusion reactions of the cycloadducts under formation of

  图形摘要摘要描述了2,5-二-叔丁基噻吩S-氧化物和2,3,4,5-四(对甲苯基)噻吩S-氧化物与烯烃的环加成反应。将 2,5-二叔丁基噻吩 S-氧化物在 Diels-Alder 反应中作为二烯的反应性与 2,5-二-叔丁基噻吩 S,S-二氧化物进行比较。举例说明了在形成高度取代的芳族化合物的情况下环加合物的热和光化学 SO 挤出反应。