α-羰基-N-[(R)-1-苯基乙基]苯基乙酰胺 | 10549-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: α-羰基-N-[(R)-1-苯基乙基]苯基乙酰胺
• 中文别名: Alpha-羰基-N-[(R)-1-苯基乙基]苯基乙酰胺
• 英文名称: (R)-(+)-2-oxo-2-phenyl-N-(1-phenylethyl)acetamide
• 英文别名: 2-Oxo-2-phenyl-N-[(1R)-1-phenylethyl]acetamide
• CAS: 10549-15-2
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: KCDFERKGOUXJDD-GFCCVEGCSA-N

物化性质

• 熔点：
  110-112 °C(lit.)
• 密度：
  1.144±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  避免使用强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  α-羰基-N-[(R)-1-苯基乙基]苯基乙酰胺 在 草酰氯 、 sodium acetate 、 dinitrogen tetraoxide 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 反应 2.5h， 生成 (S)-(-)-α-cyano-α-fluorophenylacetyl chloride
  参考文献：
  名称：

  Takeuchi, Yoshio; Itoh, Noriaki; Note, Hiroshi, Journal of the American Chemical Society, 1991, vol. 113, # 16, p. 6318 - 6320

  摘要：

  DOI：
• 作为产物：
  描述：

  氧代(苯基)乙酰氯 、 R(+)-alpha-甲基苄胺 以 苯 为溶剂， 生成 α-羰基-N-[(R)-1-苯基乙基]苯基乙酰胺
  参考文献：
  名称：

  Sterically controlled synthesis of optically active organic compounds. V. Sterically controlled synthesis of optically active .alpha.-amino acids from .alpha.-oxo acids by reductive amination

  摘要：

  DOI：

  10.1021/jo01281a020

文献信息

• Selective amidation by a photocatalyzed umpolung reaction
  作者：Debasish Ghosh、Rajesh Nandi、Saikat Khamarui、Sukla Ghosh、Dilip K. Maiti

  DOI：10.1039/c9cc01079c

  日期：——

  Herein, a metal-catalyzed organic transformation merged with another organophotocatalyst has been developed under mild conditions for the production of α-ketoamides.

  在此，已经开发了一种金属催化的有机转化，与另一种有机光催化剂在温和条件下结合，用于生产α-酮酰胺。
• A novel approach for the one-pot preparation of α-ketoamides by anodic oxidation
  作者：Zhenlei Zhang、Jihu Su、Zhenggen Zha、Zhiyong Wang

  DOI：10.1039/c3cc43685c

  日期：——

  The direct oxidative synthesis of α-ketoamides via anodic oxidation was developed by using dioxygen as a reactant under mild conditions. This methodology has a broad substrate scope (aromatic amines, aliphatic amines and ammonium acetate) and opens up an interesting and attractive avenue for the synthesis of α-ketoamide derivatives.

  在温和的条件下，以二氧为反应物，开发了通过阳极氧化直接氧化合成δ±-酮酰胺的方法。这种方法的底物范围很广（芳香胺、脂肪胺和醋酸铵），为合成δ-酮酰胺衍生物开辟了一条有趣而有吸引力的途径。
• Chemistry of novel compounds with multifunctional carbon structure. 9. Molecular design, synthetic studies, and NMR investigation of several efficient chiral derivatizing reagents which give very large 19F NMR .DELTA..delta. values in enantiomeric excess determination
  作者：Yoshio Takeuchi、Noriaki Itoh、Toshihiro Satoh、Toru Koizumi、Kentaro Yamaguchi

  DOI：10.1021/jo00059a036

  日期：1993.3

  In order to develop efficient ee-determining reagents potentially superior to MTPA (1), some multifunctional compounds 2-5 were rationally designed. From NMR investigations of the analogous diastereomeric derivatives it was found that the chemical shift differences for each pair of diastereomers (DELTAdelta values) for CFPA derivatives 5d-f were approximately five times greater in F-19 NMR spectra and two times greater in H-1 NMR spectra than those of 1d-f. Synthesis of the optically pure CFPA, (-)-5a and (+)-5a, was achieved by nitrosation of each diastereomer of the optically active N-(1-phenylethyl)amides, 5f(M) and 5f(L), followed by thermal decomposition. Various derivatives were prepared by the condensation of 5b and lb with alcohol and amine nucleophiles, and both DELTAdelta(F) and DELTAdelta(H) Values were obtained for each compound. The CFPA derivatives 5d-m have proven to be significantly superior for ee determinations when compared to the corresponding MTPA derivatives 1d-m, particularly in compounds having remotely disposed chiral centers.
• Diastereoselective reduction and carboncarbon bond formation of α-keto esters/amides with SmI2
  作者：Shin-ichi Fukuzawa、Manabu Miura、Hiroshi Matsuzawa

  DOI：10.1016/s0040-4039(01)00676-1

  日期：2001.6

  The stereoselective reduction of alpha -keto esters/alpha -keto amides, which have various chiral auxiliaries using SmI2, is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)- and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries that produced the corresponding alpha -hydroxy ester and amide in good diastereoselectivity with satisfactory yields. Allylation, the Reformatsky-type reaction, and the ketyl-alkene coupling reaction with the 1,1,2(R)-triphenylethanediol and 2(S)-methoxymethylpyrrolidine, derivative of the alpha -keto ester/amide proceeded smoothly with high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• TAKEUCHI, YOSHIO;ITOH, NORIAKI;NOTE, HIROSHI;KOIZUMI, TORU;YAMAGUCHI, KEN+, J. AMER. CHEM. SOC., 113,(1991) N6, C. 6318-6320
  作者：TAKEUCHI, YOSHIO、ITOH, NORIAKI、NOTE, HIROSHI、KOIZUMI, TORU、YAMAGUCHI, KEN+

  DOI：——

  日期：——