benzyl N-(2,6-dimethylphenyl)carbamate | 156267-16-2

• 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: benzyl N-(2,6-dimethylphenyl)carbamate
• 英文别名: Phenylmethyl N-(2,6-dimethylphenyl)carbamate
• CAS: 156267-16-2
• 化学式: C₁₆H₁₇NO₂
• mdl: MFCD05874786
• 分子量: 255.316
• InChiKey: ZDICVHRNUIVZNU-UHFFFAOYSA-N

物化性质

• 沸点：
  346.1±41.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 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：

  benzyl N-(2,6-dimethylphenyl)carbamate 在 氢气 、 sodium hydride 作用下， 生成 N,2,6-三甲基苯胺
  参考文献：
  名称：

  Rewcastle, Gordon W.; Denny, William A., Heterocycles, 1994, vol. 37, # 2, p. 701 - 708

  摘要：

  DOI：
• 作为产物：
  描述：

  氯甲酸苄酯 、 2,6-二甲基苯胺 在 十六烷基三甲基溴化铵 作用下， 以 水 为溶剂， 反应 0.17h， 以65%的产率得到benzyl N-(2,6-dimethylphenyl)carbamate
  参考文献：
  名称：

  A catalyst-free N-benzyloxycarbonylation of amines in aqueous micellar media at room temperature

  摘要：

  N-Benzyloxycarbonylation of amines was carried out in aqueous micellar media. Aliphatic (open and cyclic), aromatic and heteroaromatic amines react with Cbz-Cl to give excellent yields of products. The reactions were carried out in water and at room temperature. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.010

文献信息

• Modified Graphene Oxide Based Zinc Composite: an Efficient Catalyst for N-formylation and Carbamate Formation Reactions Through CO₂ Fixation
  作者：Resmin Khatun、Surajit Biswas、Sarikul Islam、Imdadul Haque Biswas、Sk Riyajuddin、Kaushik Ghosh、Sk Manirul Islam

  DOI：10.1002/cctc.201801963

  日期：2019.2.20

  the catalyst was very proficient for the CO2 fixation through N‐formylation and carbamate formation reactions of amines. Catalytic N‐formylation reaction of both aromatic and aliphatic amines gave high yield of corresponding formylated products in presence of polymethylhydrosiloxane (PMHS) as reducing agent under 1 bar CO2 pressure and mild temperature. Formation of carbamates from aniline or its derivatives

  通过化学反应催化固定CO 2一直是合成化学的一项艰巨任务。本文介绍了一种设计，合成了一种环保，低成本，含锌金属的非均相改性胺类氧化石墨烯催化剂。催化剂的表征已通过拉曼光谱和FTIR光谱，AAS，XRD，TEM，SEM，EDX和N 2吸附脱附研究进行。发现该催化剂通过胺的N-甲酰化和氨基甲酸酯形成反应非常熟练地固定了CO 2。在1 bar CO 2下，存在聚甲基氢硅氧烷（PMHS）作为还原剂的情况下，芳族胺和脂肪族胺的N甲酰化反应可得到相应的甲酰化产物，收率很高压力和温和的温度。在我们合成的催化剂存在下，在无溶剂条件下，在相同的CO 2压力下，也可以在相同的CO 2压力下，由苯胺或其衍生物和烷基/芳基溴化物形成氨基甲酸酯，并具有良好的产品选择性。即使经过六个循环，催化剂仍可重复使用且高效。
• The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction: Access to Privileged Chemical Structures and Scope and Limitations of the Method
  作者：Abbegail C. Bell、Alex B. Boomsma、Niecia E. Flikweert、Robert M. Hohlman、Shiyuan Zhang、Ronald L. Blankespoor、Shannon M. Biros、Richard J. Staples、Steven J. Brickner、Michael R. Barbachyn

  DOI：10.1021/acs.joc.9b03400

  日期：2020.5.15

  antibacterial agent. Herein, we report the results of our systematic investigation into the scope and limitations of this process and have identified some distinguishing characteristics within the aryl/heteroaryl series. We also describe the first preparation of 3-aryloxazolidin-2-ones bearing new functionalized C-5 substituents derived from conjugated 1,3-dienyl and cumulated 1,2-dienyl carbamate precursors

  3-芳基和3-杂芳基恶唑烷-2-酮由于其附加取代基的细微变化后表现出的多种药理活性，因此变得越来越重要，应被视为特权化学结构。碘代环氨基甲酸酯化反应已被广泛用于制备许多3-烷基-5-（卤代甲基）恶唑烷丁-2-酮，但是相应的芳族同类物尚未得到充分开发。我们建议外消旋的3-芳基和3-杂芳基-5-（碘甲基）恶唑烷-2-酮很容易通过N-烯丙基化的N-芳基或N-杂芳基氨基甲酸酯的碘代氨基甲酸酯化反应制备，可能是快速合成中间体。制备具有生物活性的潜在铅化合物。我们通过使用这种方法制备消旋利奈唑胺（一种抗菌剂）来说明这一点。在这里 我们报告了我们对该过程的范围和局限性进行系统研究的结果，并确定了芳基/杂芳基系列中的一些区别特征。我们还描述了第一种制备带有新的功能化C-5取代基的3-芳基恶唑烷-2-酮的方法，该取代基衍生自共轭的1,3-二烯基和累积的1,2-二烯基氨基甲酸酯前体。最后，我们描述了碘代氨基甲
• Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2'-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)
  作者：Gordon W. Rewcastle、Brian D. Palmer、Ellen M. Dobrusin、David W. Fry、Alan J. Kraker、William A. Denny

  DOI：10.1021/jm00039a016

  日期：1994.6

  A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity, While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC(50)s in the range 2-25 mu M, the most active being 4-substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation.
• Direct Amidation of <i>N</i>-Boc- and <i>N</i>-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates
  作者：Diane S. W. Lim、Tedrick T. S. Lew、Yugen Zhang

  DOI：10.1021/acs.orglett.5b03061

  日期：2015.12.18

  N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.
• Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+, J. Med. Chem, 37 (1994) N 13, S 2033-2042
  作者：Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+

  DOI：——

  日期：——