N,N-dimethyl-2-(p-tolyl)propanamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N,N-dimethyl-2-(p-tolyl)propanamide
• 英文别名: N,N-dimethyl-2-(4-methylphenyl)propanamide
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: RBUVAKLNCWOLLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-(p-tolyl)propanamide 在 劳森试剂 、 palladium diacetate 、 三甲基乙酸 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 26.0h， 生成 2-(4-hydroxyphenoxy)-N,N-dimethyl-2-(p-tolyl)propanethioamide
  参考文献：
  名称：

  Pd-Catalyzed Site-Selectivep-Hydroxyphenyloxylation of Benzylic α-C(sp³)–H Bonds with 1,4-Benzoquinone

  摘要：

  A Pd-catalyzed, site-selective p-hydroxypheny-loxylation of benzylic alpha-C(sp(3))-H bonds with 1,4-benzoquinone using thioamide as a directing group is reported. 1,4-Benzoquinone is employed as the p-hydroxyphenyloxy source without extra oxidants. This method exclusively gives site selectivity at alpha-C(sp(3))-H bonds rather than the usual beta-C(sp(3))-H bonds through C-H activation mode. The reactions proceed with high functional group tolerance in yields of 42-93%.

  DOI：

  10.1021/acs.orglett.6b02782
• 作为产物：
  描述：

  对甲基苯乙酸 在 正丁基锂 、 氯化亚砜 、 二异丙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 N,N-dimethyl-2-(p-tolyl)propanamide
  参考文献：
  名称：

  Pd-Catalyzed Site-Selectivep-Hydroxyphenyloxylation of Benzylic α-C(sp³)–H Bonds with 1,4-Benzoquinone

  摘要：

  A Pd-catalyzed, site-selective p-hydroxypheny-loxylation of benzylic alpha-C(sp(3))-H bonds with 1,4-benzoquinone using thioamide as a directing group is reported. 1,4-Benzoquinone is employed as the p-hydroxyphenyloxy source without extra oxidants. This method exclusively gives site selectivity at alpha-C(sp(3))-H bonds rather than the usual beta-C(sp(3))-H bonds through C-H activation mode. The reactions proceed with high functional group tolerance in yields of 42-93%.

  DOI：

  10.1021/acs.orglett.6b02782

文献信息

• Palladium-Catalyzed Hydrocarbonylative C–N Coupling of Alkenes with Amides
  作者：Xibing Zhou、Guoying Zhang、Bao Gao、Hanmin Huang

  DOI：10.1021/acs.orglett.8b00538

  日期：2018.4.20

  An efficient palladium-catalyzed hydrocarbonylative C–N coupling of alkenes with amides has been developed. The reaction was performed via hydrocarbonylation of alkenes, followed by acyl metathesis with amides. Both intermolecular and intramolecular reactions proceed smoothly to give either branched or linear amides in high turnover number (3500) with NH4Cl or NMP·HCl as a proton source under the palladium

  已经开发了一种有效的钯催化烯烃与酰胺的烷化C–N偶联反应。该反应通过烯烃的羰基化，然后用酰胺进行酰基复分解来进行。分子间和分子内反应均能顺利进行，在钯催化下，以NH 4 Cl或NMP·HCl为质子源，可以得到高周转数（3500）的支链或直链酰胺。当廉价的NMP·DCl用作氘源时，该反应为催化氘代酰胺提供了一种方便的催化方法。
• Stereospecific Acylative Suzuki–Miyaura Cross-Coupling: General Access to Optically Active α-Aryl Carbonyl Compounds
  作者：Byeongdo Roh、Abdikani Omar Farah、Beomsu Kim、Taisiia Feoktistova、Finn Moeller、Kyeong Do Kim、Paul Ha-Yeon Cheong、Hong Geun Lee

  DOI：10.1021/jacs.3c00637

  日期：——

  stereospecific Pd-catalyzed acylative cross-coupling of enantiomerically enriched alkylboron compounds has been developed. The protocol features an extremely high level of enantiospecificity to allow facile access to synthetically challenging and valuable chiral ketones and carboxylic acid derivatives. The use of a sterically encumbered and electron-rich phosphine ligand proved to be crucial for the success

  已经开发了一种用于对映体富集的烷基硼化合物的立体特异性 Pd 催化的酰化交叉偶联的新策略。该协议具有极高水平的对映特异性，可以轻松获得具有综合挑战性和有价值的手性酮和羧酸衍生物。事实证明，空间位阻和富电子膦配体的使用对于反应的成功至关重要。此外，在实验和计算研究的基础上，已经确定了一种独特的金属转移机制，该机制由基于C(sp 3 ) 的有机硼试剂的非共价相互作用辅助。
• Pd-Catalyzed Site-Selective<i>p</i>-Hydroxyphenyloxylation of Benzylic α-C(sp³)–H Bonds with 1,4-Benzoquinone
  作者：Guangjun Song、Ziwei Zheng、Yanhui Wang、Xinhong Yu

  DOI：10.1021/acs.orglett.6b02782

  日期：2016.12.2

  A Pd-catalyzed, site-selective p-hydroxypheny-loxylation of benzylic alpha-C(sp(3))-H bonds with 1,4-benzoquinone using thioamide as a directing group is reported. 1,4-Benzoquinone is employed as the p-hydroxyphenyloxy source without extra oxidants. This method exclusively gives site selectivity at alpha-C(sp(3))-H bonds rather than the usual beta-C(sp(3))-H bonds through C-H activation mode. The reactions proceed with high functional group tolerance in yields of 42-93%.