Carbamic acid, (4-methylphenyl)-, 1-phenylethyl ester | 90591-46-1

• 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: Carbamic acid, (4-methylphenyl)-, 1-phenylethyl ester
• 英文别名: 1-phenylethyl N-(4-methylphenyl)carbamate
• CAS: 90591-46-1
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: AZDXEDUCCRCLAL-UHFFFAOYSA-N

物化性质

• 沸点：
  345.7±31.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  Carbamic acid, (4-methylphenyl)-, 1-phenylethyl ester 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.5h， 生成 methyl p-tolyl carbamic acid 1-phenylethyl ester
  参考文献：
  名称：

  N to C Aryl Migration in Lithiated Carbamates: α-Arylation of Benzylic Alcohols

  摘要：

  We report a new mode of reactivity displayed by lithiated O-benzyl carbamates carrying an N-aryl substituent: upon lithiation, the N-aryl group is transferred cleanly from N to C. An arylation of the carbamate results, providing a route to alpha,alpha-arylated secondary or tertiary alcohols. We also report density functional theory calculations supporting the proposal that arylation proceeds through a dearomatizing attack on the aromatic ring, a significantly lower energy pathway than the 1,2-acyl transfer observed with related N-alkyl carbamates.

  DOI：

  10.1021/ja808959e
• 作为产物：
  描述：

  苏合香醇 、 对甲苯异氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 Carbamic acid, (4-methylphenyl)-, 1-phenylethyl ester
  参考文献：
  名称：

  N to C Aryl Migration in Lithiated Carbamates: α-Arylation of Benzylic Alcohols

  摘要：

  We report a new mode of reactivity displayed by lithiated O-benzyl carbamates carrying an N-aryl substituent: upon lithiation, the N-aryl group is transferred cleanly from N to C. An arylation of the carbamate results, providing a route to alpha,alpha-arylated secondary or tertiary alcohols. We also report density functional theory calculations supporting the proposal that arylation proceeds through a dearomatizing attack on the aromatic ring, a significantly lower energy pathway than the 1,2-acyl transfer observed with related N-alkyl carbamates.

  DOI：

  10.1021/ja808959e

文献信息

• METHODS FOR TREATING HEPATITIS C
  申请人：Karp Gary M.

  公开号：US20100292187A1

  公开（公告）日：2010-11-18

  The present invention provides compounds, pharmaceutical compositions, and methods of using such compounds or compositions for treating infection by a virus, or for affecting viral IRES activity.

  本发明提供了化合物、药物组合物以及使用这些化合物或组合物治疗病毒感染或影响病毒IRES活性的方法。
• META-BENZAMIDINE DERIVATIVES AS SERINE PROTEASE INHIBITORS
  申请人：Protherics Molecular Design Limited

  公开号：EP1009758A1

  公开（公告）日：2000-06-21
• US7973069B2
  申请人：——

  公开号：US7973069B2

  公开（公告）日：2011-07-05
• [EN] META-BENZAMIDINE DERIVATIVES AS SERIN PROTEASE INHIBITORS<br/>[FR] DERIVES DE META-BENZAMIDINE COMME INHIBITEURS DE SERINE PROTEASE
  申请人：——

  公开号：WO1999011658A1

  公开（公告）日：1999-03-11

  [EN] The invention relates to serine protease inhibitor compound of formula (I), where R1 and R2 each independently is hydrogen or hydroxyl, alkoxyl, alkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonyl, acyloxymethoxycarbonyl or alkylamino optionally substituted by hydroxy, alkylamino, alkoxy, oxo, aryl or cycloalkyl; each R3 independently is R1, R2, amino, halo, cyano, nitro, thiol, alkylthio, alkylsulfonyl, alkylsulphenyl, alkylsulphonamido, alkylaminosulphonyl, haloalkoxy and haloalkyl; each X independently is C, N, O or S atom or a CO, CR1, C(R1)2 or NR1 group, at least one X being C, CO, CR1 or C(R1)2, with the proviso that if the benzamidine group is unsubstituted and the X-X group is -CH2C(R1)2-, then R1 is hydrogen or is attached to the alkylene carbon atom by a heteroatom; L is an organic linker group containing 1 to 5 backbone atoms selected from C, N, O and S, or a branched alkyl or cyclic group; Y is a nitrogen atom or a CR1 group or Y and L taken together form a cyclic group; Cy is a saturated or unsaturated, mono or polycyclic, homo or heterocyclic group optionally subsituted by groups R3 or phenyl optionally substituted by R3; Lp is a lipophilic organic group, selected from an alkyl, heterocyclic, alkenyl, alkaryl, cycloalkyl, polycycloalkyl, cycloalkenyl, aryl, aralkyl or haloalkyl group or a combination of two or more such groups optionally substituted by one or more of oxa, oxo, aza, thio, halo, amino, hydroxy or R3 groups; D is a hydrogen bond donor group; and n is 0, 1 or 2 and salts thereof.
  [FR] L'invention concerne des composés d'inhibiteurs de sérine protéase de la formule I (dans laquelle R1 et R2 sont chacun indépendamment hydrogène ou hydroxyle, alcoxy, alkyle, aminoalkyle, hydroxyalkyle, alcoxyalkyle, alcoxycarbonyle, acyloxyméthoxycarbonyle ou alkylamino éventuellement substitué par hydroxy, alkylamino, alcoxy, oxo, aryle ou cycloalkyle; chaque R3 est indépendamment R1, R2, amino, halo, cyano, nitro, thiol, alkylthio, alkylsulfonyle, alkylsulfényle, alkylsulfonamido, alkylaminosulfonyle, haloalcoxy et haloalkyle; chaque X est indépendamment un atome de C, N, O ou S ou un groupe CO, CR1, C(R1)2 ou NR1, au moins un X étant C, CO, CR1 ou C(R1)2, à condition que si le groupe benzamidine est non substitué et le groupe X-X est -CH2C(R1)2-, alors R1 est hydrogène ou est fixé à l'atome de carbone d'alkylène par un hétéroatome; L est un groupe de liaison organique contenant 1 à 5 atomes de squelette sélectionnés dans le groupe formé par C, N, O et S ou un alkyle ou groupe cyclique ramifié; Y est un atome de nitrogène ou un groupe CR1 ou Y et L pris ensemble forment un groupe cyclique; Cy est un groupe saturé ou insaturé, mono ou polycyclique, homo ou hétérocyclique éventuellement substitué par des groupes R3 ou un phényle éventuellement substitué par R3; Lp est un groupe organique lipophile, sélectionné dans le groupe formé par un groupe alkyle, hétérocyclique, alcényle, alkaryle, cycloalkyle, polycycloalkyle, cycloalcényle, aryle, aralkyle ou haloalkyle ou une combinaison de deux ou plusieurs de ces groupes éventuellement substitués par un ou plusieurs groupes oxa, oxo, aza, thio, halo, amino, hydroxy ou R3; D est un groupe donneur de liaison hydrogène; et n désigne 0, 1 ou 2. L'invention concerne également des sels de ces composés.
• N to C Aryl Migration in Lithiated Carbamates: α-Arylation of Benzylic Alcohols
  作者：Jonathan Clayden、William Farnaby、Damian M. Grainger、Ulrich Hennecke、Michele Mancinelli、Daniel J. Tetlow、Ian H. Hillier、Mark A. Vincent

  DOI：10.1021/ja808959e

  日期：2009.3.18

  We report a new mode of reactivity displayed by lithiated O-benzyl carbamates carrying an N-aryl substituent: upon lithiation, the N-aryl group is transferred cleanly from N to C. An arylation of the carbamate results, providing a route to alpha,alpha-arylated secondary or tertiary alcohols. We also report density functional theory calculations supporting the proposal that arylation proceeds through a dearomatizing attack on the aromatic ring, a significantly lower energy pathway than the 1,2-acyl transfer observed with related N-alkyl carbamates.