(R)-N-trifluoroacetyl-α-(1-naphthyl)ethylamine | 66964-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-trifluoroacetyl-α-(1-naphthyl)ethylamine
• 英文别名: (R)-(+)-N-(1-(1-naphthyl)ethyl)trifluoroacetamide；(R)-N-trifluoroacetyl-1-(1-naphthyl)ethylamine；2,2,2-trifluoro-N-[(1R)-1-naphthalen-1-ylethyl]acetamide
• CAS: 66964-32-7
• 化学式: C₁₄H₁₂F₃NO
• 分子量: 267.251
• InChiKey: NOJXWADZEDSEGP-SECBINFHSA-N

物化性质

• 沸点：
  381.3±42.0 °C(Predicted)
• 密度：
  1.257±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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N-trifluoroacetyl-α-(1-naphthyl)ethylamine 在 ammonia borane 、 三氟化硼乙醚 、 三(五氟苯基)硼烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以84%的产率得到(R)-N-(2,2,2-trifluoroethyl)-1-(1-naphthyl)ethylamine
  参考文献：
  名称：

  B（C6F5）3-氨硼烷催化酰胺还原为胺

  摘要：

  据报道，在温和的反应条件下，用易于获得且稳定的氨硼烷（AB）作为还原剂，将酰胺进行的首次B（C 6 F 5）3催化脱氧还原为相应的胺。该无金属方案可轻松获得各种结构多样的胺产品，且收率高至优异，并且对各种官能团（包括对还原敏感的官能团）均具有良好的耐受性。该新方法也适用于手性酰胺底物，而不会破坏对映体的纯度。BF 3  OEt 2助催化剂在该反应中的作用是通过酰胺-硼加合物的原位形成来活化酰胺羰基。

  DOI：

  10.1002/adsc.201801447
• 作为产物：
  描述：

  (R)-1-(1-萘基)乙胺 生成 (R)-N-trifluoroacetyl-α-(1-naphthyl)ethylamine
  参考文献：
  名称：

  OI, NAOBUMI;KITAHARA, HAJIMU;MATSUSHITA, YASUHIRO, J. HIGH RESOLUT. CHROMATOGR., 13,(1990) N0, C. 720-724

  摘要：

  DOI：

文献信息

• Stereoselective Reactions. XXXII. Enantioselective Deprotonation of 4-tert-Butylcyclohexanone by Fluorine-Containing Chiral Lithium Amides Derived from 1-Phenylethylamine and 1-(1-Naphthyl)ethylamine.
  作者：Kazumasa AOKI、Kenji KOGA

  DOI：10.1248/cpb.48.571

  日期：——

  examined using 1-phenylethylamine- and 1-(1-naphthyl)ethylamine-derived chiral lithium amides having an alkyl or a fluoroalkyl substituent at the amide nitrogen. The lithium amides having a 2,2,2-trifluoroethyl group on the amide nitrogen are easily accessible in both enantiomeric forms, and were found to induce good enantioselectivity in the present reaction.

  使用衍生自在酰胺氮上具有烷基或氟代烷基取代基的1-苯基乙胺和1-（1-萘基）乙胺衍生的手性锂酰胺，研究了4-叔丁基环己酮的对映选择性去质子化。酰胺氮上具有2,2,2-三氟乙基的氨基酰胺很容易以两种对映体形式进入，并且发现在本反应中诱导了良好的对映选择性。
• Carbon–Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)–CF₃ Bond Cleavage
  作者：Longzhi Zhu、Liyuan Le、Mingpan Yan、Chak-Tong Au、Renhua Qiu、Nobuaki Kambe

  DOI：10.1021/acs.joc.9b00583

  日期：2019.5.3

  The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF3 group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates

  描述了三氟乙酰酰胺与格氏试剂的反应，以用各种烷基或芳基取代CF 3基团。各种芳基，喹啉-8-基和（杂）烷基官能团以及F，Cl和Br原子均具有良好的耐受性。这些水分稳定且易于获得的三氟乙酰基酰胺可以方便地获得，并用作异氰酸酯的新型通用前体。对照实验表明，反应是通过异氰酸酯中间体和/或醇盐/酰胺双阴离子中间体进行的。
• A convenient family of chiral shift reagents for measurement of enantiomeric excesses of sulfoxides
  作者：M. Deshmukh、E. Duñach、S. Juge、H.B. Kagan

  DOI：10.1016/s0040-4039(01)91049-4

  日期：——
• Lanthanide-chiral resolving agent mixtures as chiral NMR shift reagents
  作者：Thomas J. Wenzel、Celeste A. Morin、Alice A. Brechting

  DOI：10.1021/jo00039a017

  日期：1992.6

  Mixtures of lanthanide complexes with soluble analogs of chiral liquid chromatographic stationary phases are shown to be useful NMR shift reagents for determining enantiomeric exceeds. The chiral resolution agents used in this work exhibit different association constants with enantiomeric substrates and associate weakly, if at all, with lanthanide ions. If the lanthanide associates with the substrate, the resolution observed in the spectrum of the substrate is enhanced. Enhancement occurs because the enantiomer concentrated in the bulk solution spends more time bonded to the lanthanide ion than the enantiomer with a higher association constant with the chiral resolving agent. Since the mechanism of interaction of many chiral liquid chromatographic phases is understood, or offers the potential to be understood, it should be possible to assign absolute configurations to the resolved NMR spectra. The method is applicable with donor-acceptor chiral resolving agents such N-(3,5-dinitrobenzoyl)-L-leucine and chiral hosts such as the cyclodextrins.
• B(C ₆ F ₅ ) ₃ ‐Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane
  作者：Yixiao Pan、Zhenli Luo、Jiahong Han、Xin Xu、Changjun Chen、Haoqiang Zhao、Lijin Xu、Qinghua Fan、Jianliang Xiao

  DOI：10.1002/adsc.201801447

  日期：2019.5.14

  The first B(C6F5)3‐catalyzed deoxygenative reduction of amides into the corresponding amines with readily accessible and stable ammonia borane (AB) as a reducing agent under mild reaction conditions is reported. This metal‐free protocol provides facile access to a wide range of structurally diverse amine products in good to excellent yields, and various functional groups including those that are reduction‐sensitive

  据报道，在温和的反应条件下，用易于获得且稳定的氨硼烷（AB）作为还原剂，将酰胺进行的首次B（C 6 F 5）3催化脱氧还原为相应的胺。该无金属方案可轻松获得各种结构多样的胺产品，且收率高至优异，并且对各种官能团（包括对还原敏感的官能团）均具有良好的耐受性。该新方法也适用于手性酰胺底物，而不会破坏对映体的纯度。BF 3  OEt 2助催化剂在该反应中的作用是通过酰胺-硼加合物的原位形成来活化酰胺羰基。