4-氯-n-(3,5-二甲基苯基)苯甲酰胺 | 127292-04-0

• 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: 4-氯-n-(3,5-二甲基苯基)苯甲酰胺
• 英文名称: N-(3,5-dimethylphenyl)-4-chlorobenzamide
• 英文别名: 4-chloro-N-(3,5-dimethylphenyl)benzamide
• CAS: 127292-04-0
• 化学式: C₁₅H₁₄ClNO
• mdl: MFCD00783850
• 分子量: 259.735
• InChiKey: RLHLIMJZJKUOGM-UHFFFAOYSA-N

物化性质

• 熔点：
  130-133 °C
• 沸点：
  319.4±42.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  3,5-二甲基苯基异氰酸酯 在 potassium fluoride 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 以 1,4-二氧六环 为溶剂， 反应 32.0h， 生成 4-氯-n-(3,5-二甲基苯基)苯甲酰胺
  参考文献：
  名称：

  Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

  摘要：

  N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.

  DOI：

  10.1021/acs.orglett.5b03061

文献信息

• Practical one-pot amidation of <i>N</i>-Alloc-, <i>N</i>-Boc-, and <i>N</i>-Cbz protected amines under mild conditions
  作者：Wan Pyo Hong、Van Hieu Tran、Hee-Kwon Kim

  DOI：10.1039/d1ra02242c

  日期：——

  A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and

  已经描述了由N - Alloc-、N - Boc- 和N -Cbz-保护的胺轻松一锅合成酰胺。该反应涉及使用在 2-氯吡啶和三氟甲磺酰酐存在下原位生成的异氰酸酯中间体与格氏试剂反应生成相应的酰胺。使用该反应方案，多种N - Alloc-、N - Boc- 和N -Cbz-保护的脂肪胺和芳基胺以高产率有效地转化为酰胺。该方法对酰胺的合成非常有效，并为简便的酰胺化提供了一种有前途的方法。
• Anticonvulsant Activity of Some 4-Methoxy- and 4-Chlorobenzanilides
  作者：C. Randall Clark、Carl L. McMillian

  DOI：10.1002/jps.2600790308

  日期：1990.3

  A series of mono-, di-, and trimethylated derivatives of 4-chloro- and 4-methoxybenzanilide was synthesized and evaluated for anticonvulsant activity. This series was prepared in the course of studies designed to examine the relationship between anticonvulsant effects and benzamide structure. The compounds were tested in mice against seizures induced by maximal electroshock (MES) and pentylenetetrazole

  合成了一系列4-氯-和4-甲氧基苯甲腈的单，二和三甲基化衍生物，并评估了其抗惊厥活性。该系列是在研究过程中准备的，旨在研究抗惊厥作用与苯甲酰胺结构之间的关系。在小鼠中对化合物进行了测试，以防最大电击（MES）和戊四氮（scMet）诱发的癫痫发作，以及用旋翼仪测定神经功能缺损。在腹膜内给药的小鼠中，4-甲氧基-2，6-二甲基苯甲酰苯胺（4）在MES测试中显示中位抗惊厥药效价（ED50）为18.58 mg / kg，在旋翼车中显示中位毒性（TD50）为133.72 mg / kg检测，得到的保护指数（PI ＝ TD50 / ED50）为7.2。在口服给予4的小鼠中，抗MES ED50为27.40 mg / kg，确定的TD50剂量为342。
• Copper(<scp>i</scp>)-catalyzed amidation reaction of organoboronic esters and isocyanates
  作者：Tedrick Thomas Salim Lew、Diane Shu Wen Lim、Yugen Zhang

  DOI：10.1039/c5gc01374g

  日期：——

  A simple and efficient methodology for the preparation of amides from easily available organoboronic esters and isocyanates has been accomplished using ligand-free copper(I) catalyst. The reaction system demonstrated broad substrate...

  使用不含配体的铜（I）催化剂已经完成了一种简单有效的方法，由易于获得的有机硼酸酯和异氰酸酯制备酰胺。反应体系显示出广泛的底物...
• Direct Amidation of <i>N</i>-Boc- and <i>N</i>-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates
  作者：Diane S. W. Lim、Tedrick T. S. Lew、Yugen Zhang

  DOI：10.1021/acs.orglett.5b03061

  日期：2015.12.18

  N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.