1,2-Ethanediylbis(phenylmethyl carbamate) | 18807-67-5

• 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: 1,2-Ethanediylbis(phenylmethyl carbamate)
• 英文别名: N,N'-bis(carbobenzoxy)ethane-1,2-diamine；N,N'-ethanediyl-bis-carbamic acid dibenzyl ester；N,N'-Aethandiyl-bis-carbamidsaeure-dibenzylester；N,N'-Dibenzyloxycarbonylaethylendiamin；Bis(benzyloxycarbonyl)ethylendiamin；(2-Benzyloxycarbonylamino-ethyl)-carbamic acid benzyl ester；benzyl N-[2-(phenylmethoxycarbonylamino)ethyl]carbamate
• CAS: 18807-67-5
• 化学式: C₁₈H₂₀N₂O₄
• mdl: MFCD11054212
• 分子量: 328.368
• InChiKey: WVZPWYPJUMOHPS-UHFFFAOYSA-N

物化性质

• 熔点：
  168-169 °C
• 沸点：
  538.1±50.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：2-8°C，干燥

反应信息

• 作为反应物：
  描述：

  1,2-Ethanediylbis(phenylmethyl carbamate) 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 以55%的产率得到N-苄氧羰基乙二胺盐酸盐
  参考文献：
  名称：

  Doxorubicin immunoconjugates containing bivalent, lysosomally-Cleavable dipeptide linkages

  摘要：

  Bivalent doxorubicin (DOX)-dipeptides (16a-c) were prepared and conjugated to the monoclonal antibody BR96. The dipeptides are cleaved by lysosomal proteases following internalization of the resulting immunoconjugates. Conjugate 18b demonstrated antigen-specific in vitro tumor cell killing activity (IC50 = 0.2 muM) that was equipotent to DOX with a near doubling of drug molecules/MAb. Size exclusion chromatography showed 18b to be a noncovalent dimer that was formed immediately upon conjugation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00194-4
• 作为产物：
  描述：

  乙二胺 在 氯甲酸苄酯 作用下， 生成 1,2-Ethanediylbis(phenylmethyl carbamate)
  参考文献：
  名称：

  An Unusual Presentation of Tarsal Tunnel Syndrome Caused by an Inflatable Ice Hockey Skate

  摘要：

  背景：跗骨隧道综合征是一种罕见的局限性神经病。在运动员中，它通常是重复性活动、局部损伤或空间占位性病变的结果。方法：对一名 37 岁的男性休闲曲棍球运动员进行了临床和电生理学检查，原因是他在打曲棍球时左脚脚趾麻木，而他穿的充气冰上曲棍球冰鞋是为了更好地贴合脚部。混合性和运动性足底神经反应的振幅减小，并伴有颤动电位和正尖波，没有传导阻滞的证据，这表明主要病理变化是轴索缺失。随访检查显示，患者在停止穿着充气冰球冰鞋后，临床和电生理状况均有明显改善。结论：我们报告了一例因冰上曲棍球充气冰鞋引起的不寻常的跗骨隧道综合征，患者在停穿该冰鞋后，临床症状和电生理症状均有所改善。

  DOI：

  10.1017/s0317167100002274

文献信息

• 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.
• Dynamic Kinetic Asymmetric Allylation of Hydrazines and Hydroxylamines
  作者：Ian Mangion、Neil Strotman、Michael Drahl、Jason Imbriglio、Erin Guidry

  DOI：10.1021/ol901185d

  日期：2009.8.6

  Hydrazines and hydroxylamines have been found to be excellent nucleophiles for the palladium-catalyzed dynamic asymmetric allylic amination of vinyl epoxide, with good yields and enantioselectivities of up to 97% ee. This method is applicable to acyclic and heterocyclic amines and was applied toward a five-step synthesis of (R)-piperazic acid.
• Alkylation of Serine at the Active Site of Trypsin
  作者：WILLIAM B. LAWSON、M. DAVID LEAFER、ANNEMARIE TEWES、G. J. S. RAO

  DOI：10.1515/bchm2.1968.349.1.251

  日期：1968.1
• Reaktionen mit 1-Chlorocarbonylbenzotriazol; II¹. Synthese von Carbamidsäure-estern und verwandten Verbindungen
  作者：I. BUTULA、Lj. ČURKOVIĆ、M. V. PROŠTENIK、V. VELA、F. ZORKO

  DOI：10.1055/s-1977-24543

  日期：——
• Redmore, Derek; Dhawan, Balram, Phosphorus and Sulfur and the Related Elements, 1983, vol. 16, p. 233 - 238
  作者：Redmore, Derek、Dhawan, Balram

  DOI：——

  日期：——