N-(2,4,5-trimethyl-benzyl)-acetamide | 10519-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2,4,5-trimethyl-benzyl)-acetamide
• 英文别名: N-(2,4,5-Trimethylphenyl)acetamide；N-(2,4,5-trimethylbenzyl)acetamide；N-(2,4,5-trimethyl-benzyl)-acetamide；1¹-Acetamino-1.2.4.5-tetramethyl-benzol；N-(2,4,5-Trimethyl-benzyl)-acetamid；Essigsaeure-(2.4.5-trimethyl-benzyl-amid)；N-[(2,4,5-trimethylphenyl)methyl]acetamide
• CAS: 10519-73-0
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: AOAZLRKQVKXBAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为产物：
  描述：

  1,2,4,5-四甲苯 、 乙腈 在 Selectfluor 作用下， 以 水 为溶剂， 生成 N-(2,4,5-trimethyl-benzyl)-acetamide
  参考文献：
  名称：

  水对甲基取代的F-TEDA-BF 4苯衍生物中苯环功能化的显着影响

  摘要：

  各种NF试剂与六甲基苯（1）在质子溶剂中反应形成侧链取代的醇盐或酯，在三氟乙酸存在下在乙腈中观察到Ritter型侧链官能化，而在乙腈水溶液中发生苯环转化，开始以ipso攻击水和进一步重新排列甲基为主要过程。重排的2,3,4,5,6,6-六甲基环己-2,4-二烯酮（7）被转化为5-氟-2,3,5,6,6-五甲基-4-亚甲基环己基-2-en- 1-酮（8）或5-羟基-2,3,5,6,6-五甲基-4-亚甲基环己基-2-烯-1-酮（9）。1,2,3,4,5,6-六甲基双环[2.2.0] hexa-2,5-二烯与F-TEDA-BF 4反应在水的存在下，以高收率形成7。Durene（12）对水的ipso攻击行为与1类似，但另一方面1,2,3,4-四甲基苯具有不同的区域选择性，并形成2,3,4,5-四甲基苯酚，进一步转化为4-氟- 2,3,4,5-四甲基环己-2,5-二烯酮。遵守二阶速率方程v = d [NF]

  DOI：

  10.1021/jo060213s

文献信息

• Deprotonation of methylarene cation radicals in acetonitrile. An unexpected second-order mechanism
  作者：Vernon D. Parker、Mats. Tilset

  DOI：10.1021/ja00280a039

  日期：1986.10

  L'etude est faite par voltammetrie cyclique et par voltammetrie a balayage lineaire, dans l'acetonitrile

  L'etude est faite par voltammetrie cyclique et par voltammetrie a balayage lineaire, dans l'acetonitrile
• Kinetics and mechanism of aromatic oxidative substitutions via electron transfer. Application of Marcus theory to organic processes in the endergonic region
  作者：C. J. Schlesener、C. Amatore、J. K. Kochi

  DOI：10.1021/ja00324a027

  日期：1984.6
• Structural Effects in the TiO2-Photocatalyzed Oxidation of Alkylaromatic Compounds in Acetonitrile in the Presence of Ag2SO4
  作者：Enrico Baciocchi、Cesare Rol、Giovanni V. Sebastiani、Luca Taglieri

  DOI：10.1021/jo00097a031

  日期：1994.9

  The TiO2-sensitized photochemical reactions of some alkylbenzenes (ArCH(2)R; R = H, Me), 1-aryl-2-propanols, and corresponding methyl ethers (ArCH2C(OR'')R'CH3; R', R'' = H, Me) have been investigated in MeCN, in the presence of Ag2SO4, which traps the photogenerated electrons. With ArCH(2)R, the corresponding radical cations are generated by the photoexcited TiO2 and are then deprotonated to form benzyl radicals; from the latter 1,2-diarylethanes, 3-arylpropanonitriles, and benzylacetamides are obtained as major products. With ArCH2C(OR'')R'CH3, the formed radical cations undergo C-C bond cleavage as the only observed route, when Ar = Ph. However, when Ar = 4-MeOPh and R' = H, the radical cation undergoes C-H bond cleavage as the major or exclusive reaction path. These results are compared with those obtained in the corresponding homogeneous photochemical reactions, and their implications with respect to the role of the structure on the side-chain reactivity of aromatic radical cations are discussed.
• Bewick,A. et al., Justus Liebigs Annalen der Chemie, 1978, p. 41 - 53
  作者：Bewick,A. et al.

  DOI：——

  日期：——
• Remarkable Effect of Water on Functionalization of the Phenyl Ring in Methyl-Substituted Benzene Derivatives with F-TEDA-BF₄
  作者：Petra Kralj、Marko Zupan、Stojan Stavber

  DOI：10.1021/jo060213s

  日期：2006.5.1

  reagents reacted with hexamethylbenzene (1) forming side chain substituted alkoxides or esters in protic solvents, Ritter type side chain functionalization was observed in acetonitrile in the presence of trifluoroacetic acid, while in aqueous acetonitrile solution phenyl ring transformation took place, starting with ipso attack of water and further rearrangement of the methyl group as the main process. Rearranged

  各种NF试剂与六甲基苯（1）在质子溶剂中反应形成侧链取代的醇盐或酯，在三氟乙酸存在下在乙腈中观察到Ritter型侧链官能化，而在乙腈水溶液中发生苯环转化，开始以ipso攻击水和进一步重新排列甲基为主要过程。重排的2,3,4,5,6,6-六甲基环己-2,4-二烯酮（7）被转化为5-氟-2,3,5,6,6-五甲基-4-亚甲基环己基-2-en- 1-酮（8）或5-羟基-2,3,5,6,6-五甲基-4-亚甲基环己基-2-烯-1-酮（9）。1,2,3,4,5,6-六甲基双环[2.2.0] hexa-2,5-二烯与F-TEDA-BF 4反应在水的存在下，以高收率形成7。Durene（12）对水的ipso攻击行为与1类似，但另一方面1,2,3,4-四甲基苯具有不同的区域选择性，并形成2,3,4,5-四甲基苯酚，进一步转化为4-氟- 2,3,4,5-四甲基环己-2,5-二烯酮。遵守二阶速率方程v = d [NF]