Phenylmethyl dibutylcarbamate | 106775-54-6

• 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: Phenylmethyl dibutylcarbamate
• 英文别名: benzenyl dibutylcarbamate；dibutyl-carbamic acid benzyl ester；Dibutyl-carbamidsaeure-benzylester；benzyl N,N-dibutylcarbamate
• CAS: 106775-54-6
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: GHEZUZFDWXDGFC-UHFFFAOYSA-N

物化性质

• 沸点：
  359.3±12.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二正丁胺 、 氯甲酸苄酯 生成 Phenylmethyl dibutylcarbamate
  参考文献：
  名称：

  丁二烯-丙烯腈橡胶的挤出塑性

  摘要：

  DOI：

  10.1021/ie50517a041

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。
• 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.
• Polyethylene Glycol–Enhanced Chemoselective Synthesis of Organic Carbamates from Amines, CO₂, and Alkyl Halides
  作者：De-Lin Kong、Liang-Nian He、Jin-Quan Wang

  DOI：10.1080/00397911.2010.517890

  日期：2011.11.15

  An efficient and environmentally benign method for the synthesis of organic carbamates was developed. Amines, CO2, and alkyl halides underwent a three-component reaction with the aid of K2CO3 and polyethylene glycol (PEG, MW 400), affording the organic carbamates under ambient conditions. PEG could presumably act as a solvent and phase-transfer catalyst (PTC). Notably, the presence of PEG could also depress the alkylation of both the amine and the carbamate, thus resulting in enhanced selectivity toward the target carbamate.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• HORI YUJI; NAGANO YOSHIAKI; NAKAO JUNJI; FUKUHARA TAKASHI; TANIGUCHI HIRO+, CHEM. EXPRESS, 1,(1986) N 4, 224-227
  作者：HORI YUJI、 NAGANO YOSHIAKI、 NAKAO JUNJI、 FUKUHARA TAKASHI、 TANIGUCHI HIRO+

  DOI：——

  日期：——
• ANTIBACTERIAL 4,5-SUBSTITUTED AMINOGLYCOSIDE ANALOGS HAVING MULTIPLE SUBSTITUENTS
  申请人：Swayze Eric E.

  公开号：US20130005674A1

  公开（公告）日：2013-01-03

  The present invention is directed to analogs of aminoglycoside compounds as well as their preparation and use as prophylactic or therapeutics against microbial infection.