N,N'-bisbenzyloxycarbonyl-p-phenylenediamine | 6324-63-6

• 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: N,N'-bisbenzyloxycarbonyl-p-phenylenediamine
• 英文别名: 1,4-Phenylenebis(phenylmethyl carbamate)；dibenzyl 1,4-phenylenedicarbamate；N,N'-p-phenylene-bis-carbamic acid dibenzyl ester；N,N'-p-Phenylen-bis-carbamidsaeure-dibenzylester；N.N'-p-Phenylen-dicarbamidsaeure-dibenzylester；N.N'-Bis-benzyloxycarbonyl-p-phenylendiamin；Dibenzyl benzene-1,4-diylbiscarbamate；benzyl N-[4-(phenylmethoxycarbonylamino)phenyl]carbamate
• CAS: 6324-63-6
• 化学式: C₂₂H₂₀N₂O₄
• mdl: MFCD18429402
• 分子量: 376.412
• InChiKey: SNFCBVWYMIBEOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bisbenzyloxycarbonyl-p-phenylenediamine 在 lead(IV) acetate 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 48.0h， 生成 benzyl (4-(((benzyloxy)carbonyl)amino)phenyl)(((4-chlorophenyl)(methyl)amino)methyl)carbamate
  参考文献：
  名称：

  Reactions of p-Benzoquinone Diimine Derivatives withN,N-Dimethylanilines

  摘要：

  N,N′-双烷氧羰基-对苯醌二亚胺与N,N-二甲基苯胺进行热加成反应，在亚胺基团与N-甲基基团之间形成N-C键。在光照下，该反应被加速。该反应对于除了甲基之外的N-烷基取代苯胺并不进行。

  DOI：

  10.1246/cl.1988.51
• 作为产物：
  描述：

  氯甲酸苄酯 、 对苯二胺 在 sodium hydroxide 作用下， 生成 N,N'-bisbenzyloxycarbonyl-p-phenylenediamine
  参考文献：
  名称：

  Zur Charakterisierung der1,3,5-Amino-sulfo-benzoesäureundähnlicher氨基-磺基-碳-脲。（4. Mitteilungüber硫代碳素脲）

  摘要：

  DOI：

  10.1002/hlca.194402701141

文献信息

• Highly selective generation of urethanes from amines, carbon dioxide and alkyl chlorides
  作者：William D. McGhee、Yi Pan、Dennis P. Riley

  DOI：10.1039/c39940000699

  日期：——

  Generation of carbamate anions from either a primary or secondary amine, carbon dioxide and a stoichiometric amount of a pentaalkylguanidine followed by the addition of alkyl chlorides gives high yields of urethanes.

  首先或次级胺、二氧化碳和一个等摩尔量的五烷基胍通过生成氨基甲酸酯阴离子的过程，随后加入烷基氯化物，可以高收率地得到尿烷。
• Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of 2,3-Disubstituted Indolines
  作者：Wei-Yang Ma、Coralie Gelis、Damien Bouchet、Pascal Retailleau、Xavier Moreau、Luc Neuville、Géraldine Masson

  DOI：10.1021/acs.orglett.0c03947

  日期：2021.1.15

  cycloaddition of β-substituted ene- and thioenecarbamates as well as cyclic enamides with quinone diimides catalyzed by a BINOL- and SPINOL-derived phosphoric acid is reported. A wide variety of 2,3-disubstituted 2-aminoindolines, including polycyclic ones, were prepared in generally high yields (up to 98%) with moderate to complete diastereoselectivities and in most cases excellent enantioselectivities

  据报道，由BINOL和SPINOL衍生的磷酸催化β-取代的烯和硫代氨基甲酸酯以及对环二酰胺与醌二酰亚胺的高度对映和区域选择性（3 + 2）形式环加成反应。通常以高收率（高达98％），中等至完全非对映选择性以及大多数情况下极好的对映选择性（高达99％ee）制备各种2，3-二取代的2-氨基二氢吲哚，包括多环吲哚。
• Practical Access to meta‐Substituted Anilines by Amination of Quinone Imine Ketals Derived from Anisidines: Efficient Synthesis of Anti‐Psychotic Drugs
  作者：Naveen Yadav、Neha Taneja、Dulal Musib、Chinmoy Kumar Hazra

  DOI：10.1002/anie.202301166

  日期：——

  is reported based on a one-pot procedure. The strategy is based on direct C−N bond formation for the practical synthesis of meta-substituted anilines, thus reversing the conventional site-selectivity. A concise and efficient synthesis of anti-psychotics and in particular of anti-schizophrenic drugs is shown.

  Brønsted 酸催化芳基胺与脂肪族胺、杂环胺和芳香胺的间位胺化反应基于一锅法进行了报道。该策略基于直接 C−N 键形成，用于间位取代苯胺的实际合成，从而逆转了传统的位点选择性。显示了抗精神病药，特别是抗精神分裂症药物的简明有效的合成。
• Carbon Dioxide as a Phosgene Replacement: Synthesis and Mechanistic Studies of Urethanes from Amines, CO2, and Alkyl Chlorides
  作者：William McGhee、Dennis Riley、Kevin Christ、Yi Pan、Barry Parnas

  DOI：10.1021/jo00114a035

  日期：1995.5

  Several carbamate esters were synthesized from amines, carbon dioxide, and alkyl chlorides. The effect of added base on the yield and selectivity of carbamate ester formation was found to be highly important with the use of sterically hindered guanidine bases giving the best results. Relative rate studies were carried out giving the following order of reactivity between carbamate anions in acetonitrile with benzyl chloride giving carbamate esters: Et(2)NCO(2)(-) = Bu(2)NCO(2)(-) > t-BuNHCO(2)(-) CyNHCO(2)(-) = s-BuNHCO(2)(-) > PhNHCO(2)(-) > CyCH(2)NHCO(2) = n-octylNHCO(2)(-) = n-BuNHCO(2)(-). Rate studies were carried out with the diethyl, s-butyl, phenyl, and n-butyl carbamates and activation parameters were determined to be Et(2)NCO(2)(-), Delta H-double dagger = 11.8 kcal/mol, Delta S-double dagger = -33 eu; s-BuNHCO(2)(-), Delta H-double dagger = 12.8 kcal/mol, Delta S-double dagger = -33 eu; PhNHCO(2)(-), Delta H-double dagger = 14.3 kcal/mol, Delta S-double dagger = -28 eu; n-BuNHCO(2)(-), Delta H-double dagger: = 23.4 kcal/mol, Delta S-double dagger = -3 eu. The unusual results obtained from the use of n-BuNHCO(2)(-) prompted further studies which showed that the rate of reaction was inversely dependent on carbon dioxide pressure (20 psig CO2, k = 4.84 x 10(-4) M(-1) s(-1); 120 psig CO2, k = 1.83 x 10(-4) M(-1) s(-1)). Nitrogen NMR spectroscopy indicated, via a labeling study with N-15 amines and C-13 enriched carbon dioxide, the formation of a doubly inserted product from the addition of two carbon dioxides to ethylamine in acetonitrile.
• Quinone Imides. XIV. Addition of Hydrogen Chloride to p-Quinonedibenzimides and Related Compounds
  作者：Roger Adams、D. S. Acker

  DOI：10.1021/ja01132a024

  日期：1952.6