乙酰胺,N-[(戊甲基苯基)甲基]- | 10519-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙酰胺,N-[(戊甲基苯基)甲基]-
• 英文名称: N-pentamethylbenzylacetamide
• 英文别名: N-Pentamethylbenzylacetamid；Acetamide, N-[(pentamethylphenyl)methyl]-；N-[(2,3,4,5,6-pentamethylphenyl)methyl]acetamide
• CAS: 10519-74-1
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: ZDPZCSZVDCSAQI-UHFFFAOYSA-N

物化性质

• 熔点：
  230-232 °C
• 沸点：
  416.0±24.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(乙酰氨基甲基)乙酰胺 、 五甲基苯 生成 乙酰胺,N-[(戊甲基苯基)甲基]-
  参考文献：
  名称：

  芳烃的酰胺烷基化

  摘要：

  Nyberg程序（在氯仿中使用三氟乙酸）进行芳烃的有效酰胺烷基化仅限于比苯更具亲核性的底物。该反应包括亲电体的质子化，裂解成碳酸根离子和通过碳酸根离子使亲核体烷基化。裂解步骤或烷基化步骤可以是速率确定的。本工作确定了某些形成碳离子但不能使亲核试剂烷基化的情况（以苯和硝基取代苯作为亲核试剂），以及其他反应条件不足以允许质子化的亲电试剂裂解的情况。N-邻苯二甲酰亚胺甲基酰胺）。

  DOI：

  10.1016/0040-4020(77)80088-4

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
• 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]
• 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
• Direct Nitrosation of Aromatic Hydrocarbons and Ethers with the Electrophilic Nitrosonium Cation
  作者：Eric Bosch、Jay K. Kochi

  DOI：10.1021/jo00098a015

  日期：1994.9

  Various polymethylbenzenes and anisoles are selectively nitrosated with the electrophilic nitrosonium salt NO+ BFI4- in good conversions and yields under mild conditions in which the conventional procedure (based on nitrite neutralization with strong acid) is ineffective. The reactivity patterns in acetonitrile deduced from the various time/conversions in Tables 2 and 3 indicate that aromatic nitrosation is distinctly different from those previously established for electrophilic aromatic nitration. The contrasting behavior of NO+ in aromatic nitrosation is ascribed to a rate-limiting deprotonation of the reversibly formed Wheland intermediate, which in the case of aromatic nitration with NO2+ occurs with no deuterium kinetic isotope effect. Aromatic nitroso derivatives (unlike the nitro counterpart) are excellent electron donors that are subject to a reversible one-electron oxidation at positive potentials significantly less than that of the parent polymethylbenzene or anisole. As a result, the series of nitrosobenzenes are also much better Bronsted bases than the corresponding nitro derivatives, and this marked distinction, therefore, accounts for the large differentiation in the deprotonation rates of their respective conjugate acids (i.e. Wheland intermediates).
• Kotani,Eiichi; Kobayashi, Shigeki; Ishii, Yoko, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 11, p. 4281 - 4291
  作者：Kotani,Eiichi、Kobayashi, Shigeki、Ishii, Yoko、Tobinaga, Seisho

  DOI：——

  日期：——

表征谱图