N-1-(2-萘基)乙基苯甲酰胺 | 3976-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-1-(2-萘基)乙基苯甲酰胺
• 英文名称: (R)-N-(1-(naphthalen-2-yl)ethyl)benzamide
• 英文别名: (R)-N-[1-(naphthalen-2-yl)ethyl]benzamide；N-[(1R)-1-naphthalen-2-ylethyl]benzamide
• CAS: 3976-23-6
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: AFJUKFYYRDHPPK-CQSZACIVSA-N

物化性质

• 熔点：
  143-145 °C
• 沸点：
  511.6±29.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (R)-(+)-1-(2-萘基)乙胺 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 potassium fluoride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 16.0h， 生成 N-1-(2-萘基)乙基苯甲酰胺
  参考文献：
  名称：

  Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.5b03061

文献信息

• COMPOUNDS AND METHODS FOR TREATING RESPIRATORY DISEASES
  申请人：Ghosh Arun K.

  公开号：US20110269834A1

  公开（公告）日：2011-11-03

  Described herein are compounds and compositions, and methods for using the compounds and compositions, for treating respiratory diseases and illness, such as severe acute respiratory syndrome (SARS).

  本文描述了化合物和组合物，以及使用这些化合物和组合物治疗呼吸道疾病和疾病，如严重急性呼吸综合征（SARS）的方法。
• Microwave-Enhanced Asymmetric Transfer Hydrogenation of<i>N</i>-(<i>tert</i>-Butylsulfinyl)imines
  作者：Óscar Pablo、David Guijarro、Miguel Yus

  DOI：10.1002/ejoc.201402884

  日期：2014.11

  This work was generously supported by the Spanish Ministerio de Ciencia e Innovacion (MICINN) (grant numbers CONSOLIDER INGENIO 2010, CSD2007-00006, CTQ2007-65218 and CTQ2011-24151) and the Generalitat Valenciana (PROMETEO/2009/039 and FEDER). O. P. thanks the Spanish Ministerio de Educacion for a predoctoral fellowship (grant number AP-2008-00989).

  这项工作得到了西班牙国家科学和创新部长 (MICINN)（授权号 CONSOLIDER INGENIO 2010、CSD2007-00006、CTQ2007-65218 和 CTQ2011-24151）和 Generalitat Valenciana (PROMETEO/FE09) 的慷慨支持。OP 感谢西班牙教育部长提供博士前奖学金（授权号 AP-2008-00989）。
• Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine
  作者：Ying Xie、Hongjie Pan、Xiao Xiao、Songlei Li、Yian Shi

  DOI：10.1039/c2ob26782a

  日期：——

  An asymmetric biomimetic transamination of aromatic ketones to optically active amines with o-HOPhCH2NH2 as amine source catalyzed by hydroquinine-derived chiral base is described. Up to 85% ee was obtained.

  描述了由氢醌衍生的手性碱催化的邻-HOPhCH 2 NH 2作为胺源的芳香族酮的不对称仿生氨基转移成旋光胺。获得了高达85％的ee。
• Asymmetric Synthesis of Chiral Primary Amines by Transfer Hydrogenation of <i>N</i>-(<i>tert</i>-Butanesulfinyl)ketimines
  作者：David Guijarro、Óscar Pablo、Miguel Yus

  DOI：10.1021/jo101057s

  日期：2010.8.6

  The diastereoselective reduction of (R)-N-(tert-butanesulfinyl)ketimines by a ruthenium-catalyzed asymmetric transfer hydrogenation process in isopropyl alcohol, followed by desulfinylation of the nitrogen atom, is an excellent method to prepare highly enantiomerically enriched α-branched primary amines (up to >99% ee) in short reaction times (1−4 h). (1S,2R)-1-Amino-2-indanol has been shown to be

  钌催化的异丙醇中钌催化的不对称转移氢化过程，对非对映选择性还原（R）-N-（叔丁烷亚磺酰基）酮亚胺，然后对氮原子进行脱亚磺酰化，是制备高度对映体富集的α-支化伯伯伯醇的绝佳方法在短的反应时间（1-4小时）内可吸收胺（ee高达99％以上）。（1秒，2 R）-1-氨基-2-茚满醇已被证明是进行这种转化的非常有效的配体。带有芳基或杂芳基和烷基作为亚胺基碳原子的取代基的酮亚胺是该方法非常好的底物。还可以实现二烷基酮亚胺的还原，从而提供具有中等旋光纯度（69％ee）的预期胺。已经以优异的产率和过量的对映体制备了一些胺，它们是非常令人感兴趣的生物学和药理学活性化合物的前体。
• Kinetic resolution of primary amines via enantioselective N-acylation with acyl chlorides in the presence of supramolecular cyclodextrin nanocapsules
  作者：Haruyasu Asahara、Toshiyuki Kida、Takuya Iwamoto、Tomoaki Hinoue、Mitsuru Akashi

  DOI：10.1016/j.tet.2013.11.097

  日期：2014.1

  non-enzymatic kinetic resolution of primary amines via enantioselective N-acylation with acyl chlorides was accomplished for the first time by using the selective sequestration of one enantiomer within a supramolecular cyclodextrin (CD) nanocapsule in nonpolar solvents. In addition, the first example of a crystalline structure for an inclusion complex between an acyl chloride and a CD derivative is reported

  通过使用超分子环糊精（CD）纳米胶囊在非极性溶剂中的选择性螯合，首次实现了通过酰氯与对映体选择性N-酰化伯胺的非酶动力学拆分。另外，报道了酰氯和CD衍生物之间的包合配合物的晶体结构的第一个例子。