2,2,2-trichloroethyl N-p-tolylcarbamate | 37934-96-6

• 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: 2,2,2-trichloroethyl N-p-tolylcarbamate
• 英文别名: 2,2,2-trichloroethyl-N-tolyl carbamate；2,2,2-trichloroethyl N-(4-methylphenyl)carbamate
• CAS: 37934-96-6
• 化学式: C₁₀H₁₀Cl₃NO₂
• 分子量: 282.554
• InChiKey: IAXVDUFXJQIBSC-UHFFFAOYSA-N

物化性质

• 沸点：
  302.1±42.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl N-p-tolylcarbamate 在 甲基三氯硅烷 、 三乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 对甲苯异氰酸酯
  参考文献：
  名称：

  Multilevel Selectivity in the Mild and High-Yielding Chlorosilane-Induced Cleavage of Carbamates to Isocyanates

  摘要：

  The silane-induced cleavage of a series of N-p-tolylcarbamates and N-phenethylcarbamates to isocyanates has been investigated as a function of chlorosilane, carbamate substituent, and reaction conditions. Reaction yields were determined from the isolated ureas, which were formed by trapping the Corresponding isocyanates with isobutylamine. Under room-temperature conditions, multilevel selectivity in carbamate activation has been demonstrated. This selectivity together with the generality of the methodology enhances the utility of carbamates as synthetic intermediates and protecting groups. To demonstrate the effectiveness of this selectivity, a series of biscarbamates were selectively monoactivated to isocyanates in excellent yields.

  DOI：

  10.1021/jo981816+
• 作为产物：
  描述：

  乙烷,三氯氟- 、 氯甲酸-2,2,2-三氯乙酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以79%的产率得到2,2,2-trichloroethyl N-p-tolylcarbamate
  参考文献：
  名称：

  Multilevel Selectivity in the Mild and High-Yielding Chlorosilane-Induced Cleavage of Carbamates to Isocyanates

  摘要：

  The silane-induced cleavage of a series of N-p-tolylcarbamates and N-phenethylcarbamates to isocyanates has been investigated as a function of chlorosilane, carbamate substituent, and reaction conditions. Reaction yields were determined from the isolated ureas, which were formed by trapping the Corresponding isocyanates with isobutylamine. Under room-temperature conditions, multilevel selectivity in carbamate activation has been demonstrated. This selectivity together with the generality of the methodology enhances the utility of carbamates as synthetic intermediates and protecting groups. To demonstrate the effectiveness of this selectivity, a series of biscarbamates were selectively monoactivated to isocyanates in excellent yields.

  DOI：

  10.1021/jo981816+

文献信息

• Copper-catalyzed Csp2–H amidation of unactivated arenes by N-tosyloxycarbamates
  作者：Alex John、Jeena Byun、Kenneth M. Nicholas

  DOI：10.1039/c3cc46412a

  日期：——

  [(Neocuproine)Cu]PF6 catalyzes the C–H amidation of unactivated arenes by N-tosyloxytrichloroethylcarbamates. Alkyl benzenes are selectively converted to aromatic amines and substituted arenes display variable regioselectivity.

  [(Neocuproine)Cu]PF6 可催化 N-tosyloxytrichloroethylcarbamates 对未活化的炔类化合物进行 CâH amidation。烷基苯被选择性地转化为芳香胺，而取代的炔烃则显示出不同的区域选择性。
• Efficient partial hydrogenation of trichloromethyl to gem-dichloromethyl groups in platinum on carbon-catalyzed system
  作者：Yoshinari Sawama、Takahiro Imanishi、Ryosuke Nakatani、Yuta Fujiwara、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1016/j.tet.2014.04.098

  日期：2014.7
• Novel Direct Synthesis of Asymmetrical Urea Compounds from Trichloroethyl Carbamates Using Catalytic DBU
  作者：Ho Seong Jang、Hee-Kwon Kim

  DOI：10.1002/bkcs.11314

  日期：2017.12
• Multilevel Selectivity in the Mild and High-Yielding Chlorosilane-Induced Cleavage of Carbamates to Isocyanates
  作者：Pek Y. Chong、Slawomir Z. Janicki、Peter A. Petillo

  DOI：10.1021/jo981816+

  日期：1998.11.1

  The silane-induced cleavage of a series of N-p-tolylcarbamates and N-phenethylcarbamates to isocyanates has been investigated as a function of chlorosilane, carbamate substituent, and reaction conditions. Reaction yields were determined from the isolated ureas, which were formed by trapping the Corresponding isocyanates with isobutylamine. Under room-temperature conditions, multilevel selectivity in carbamate activation has been demonstrated. This selectivity together with the generality of the methodology enhances the utility of carbamates as synthetic intermediates and protecting groups. To demonstrate the effectiveness of this selectivity, a series of biscarbamates were selectively monoactivated to isocyanates in excellent yields.