2,6-dideuterio-N-methylbenzamide | 1235479-17-0

• 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: 2,6-dideuterio-N-methylbenzamide
• CAS: 1235479-17-0
• 化学式: C₈H₉NO
• 分子量: 137.15
• InChiKey: NCCHARWOCKOHIH-KCZCTXNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  N-甲基苯甲酰胺 在 六氟磷酸钾 、 (p-cymene)ruthenium(II) chloride 、 重水 、 copper diacetate 作用下， 反应 24.0h， 生成 2,6-dideuterio-N-methylbenzamide
  参考文献：
  名称：

  钴（III）催化的CH活化：仲酰胺定向脱羧的炔基羧酸的脱羧官能团，其中酰胺NH-基团保持不活泼

  摘要：

  将Co（III）催化的C-H活化反应为邻苯甲酰胺（芳基/杂芳基）和吲哚衍生物的C 2烯基的-alkenylation使用炔基羧酸作为烯烃源已被开发。在二取代烯烃的形成中已经实现了高区域选择性，并且未观察到可能的环状产物。这种有效的烯基化显示了广泛的底物范围，具有良好的官能团耐受性。通过将烯基化酰胺转化为3-羟基异吲哚满酮衍生物，展示了该方法的应用。

  DOI：

  10.1002/adsc.201701406

文献信息

• Temperature-controlled redox-neutral ruthenium(<scp>ii</scp>)-catalyzed regioselective allylation of benzamides with allylic acetates
  作者：Rajendran Manikandan、Masilamani Jeganmohan

  DOI：10.1039/c6ob01498d

  日期：——

  Substituted aromatic amides reacted efficiently with allylic acetates in the presence of a cationic ruthenium complex in ClCH2CH2Cl at room temperature providing ortho allylated benzamides in a highly regioselective manner without any oxidant and base. The whole catalytic reaction occurred in a Ru(II) oxidation state and thus the oxidation step is avoided. By tuning the reaction temperature, ortho allyl

  取代的芳族酰胺在阳离子钌络合物存在下于室温在ClCH 2 CH 2 Cl中与乙酸烯丙酯有效反应，以高度区域选择性的方式提供邻位烯丙基化的苯甲酰胺，而无需任何氧化剂和碱。整个催化反应以Ru（II）氧化态发生，因此避免了氧化步骤。通过调节反应温度，仅制备邻烯丙基和乙烯基苯甲酰胺。后来，在盐酸存在下，将邻烯丙基和乙烯基化的苯甲酰胺转化为生物学上有用的六元和五元苯并内酯。
• Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C−H/N−H Activation
  作者：Todd K. Hyster、Tomislav Rovis

  DOI：10.1021/ja103776u

  日期：2010.8.4

  The oxidative cycloaddition of benzamides and alkynes has been developed. The reaction utilizes Rh(III) catalysts in the presence of Cu(II) oxidants, and is proposed to proceed by N-H metalation of the amide followed by ortho C-H activation. The resultant rhodacycle undergoes alkyne insertion to form isoquinolones in good yield. The reaction is tolerant of extensive substitution on the amide, alkyne, and arene, including halides, silyl ethers, and unprotected aldehydes as substituents. Unsymmetrical alkynes proceed with excellent regioselectivity, and heteroaryl carboxamides are tolerated leading to intriguing scaffolds for medicinal chemistry. A series of competition experiments shed further light on the mechanism of the transformation and reasons for selectivity.
• Ruthenium-Catalyzed Oxidative C–H Alkenylations of Anilides and Benzamides in Water
  作者：Lutz Ackermann、Lianhui Wang、Ratnakancana Wolfram、Alexander V. Lygin

  DOI：10.1021/ol203251s

  日期：2012.2.3

  A cationic ruthenium(II) complex enabled efficient oxidative alkenylations of anilides in water as a green solvent and proved applicable to double C-H bond functionalizations of (hetero)aromatic amides with ample scope. Detailed studies provided strong support for a change of ruthenation mechanism in the two transformations, with an irreversible metalation as the key step in cross-dehydrogenative alkenylations of benzamides.
• LOCKLEY, W. J. S., J. LABELLED COMPOUNDS AND RADIOPHARM., 1984, 21, N 2, 45-57
  作者：LOCKLEY, W. J. S.

  DOI：——

  日期：——