(R)-N-(1-phenylethyl)benzamide | 5267-67-4

• 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: (R)-N-(1-phenylethyl)benzamide
• 英文别名: N-Benzoyl-(+)-α-benzyl-aethylamin；(S)-N-(1-phenylprop-2-yl)benzamide；N-((S)-1-methyl-2-phenyl-ethyl)-benzamide；N-((S)-1-Methyl-2-phenyl-aethyl)-benzamid；benzamide-d-amphetamine；N-[(2S)-1-phenylpropan-2-yl]benzamide
• CAS: 5267-67-4
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: JHFZSLHBOLBFEV-ZDUSSCGKSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  441.3±24.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  非那明 在 氢氧化钾 作用下， 生成 (R)-N-(1-phenylethyl)benzamide
  参考文献：
  名称：

  Leithe, Chemische Berichte, 1932, vol. 65, p. 660,665

  摘要：

  DOI：

文献信息

• Ring Opening of Pymisyl‐Protected Aziridines with Organocuprates
  作者：Jan Bornholdt、Jakob Felding、Rasmus P. Clausen、Jesper L. Kristensen

  DOI：10.1002/chem.201001026

  日期：2010.11.2

  The pyrimidine‐2‐sulfonyl (pymisyl) group is introduced as a new protecting group that can be used to activate aziridines towards ring opening. It is readily introduced and removed under mild conditions. Regioselective ring opening of pymisyl‐protected 2‐methyl‐aziridine with organocuprates gives the corresponding sulfonamides in high yields, and the pymisyl group can subsequently be removed upon treatment

  引入了嘧啶-2-磺酰基（嘧啶基）作为新的保护基，可用于激活氮丙啶向开环的方向移动。它很容易在温和的条件下引入和除去。嘧啶保护的2-甲基氮丙啶与有机铜的区域选择性开环可得到高产率的相应磺酰胺，随后可在用硫醇盐处理后除去嘧啶基。这种新的氮保护基团的多功能性可以通过新合成的司来吉兰（一种用于治疗帕金森氏病的单胺氧化酶-B抑制剂）的合成来说明。
• Stereochemical studies. LIX. Asymmetric transamination from (S)-.ALPHA.-amino acids. Synthesis of optically active amines by chemical transamination of (S)-.ALPHA.-amino acid esters to ketones.
  作者：NOBUO IKOTA、KAZUO ACHIWA、SHUNICHI YAMADA

  DOI：10.1248/cpb.31.887

  日期：——

  Asymmetric synthesis of optically active amines (15) by catalytic hydrogenation and chemical transamination of the schiff bases (10) of (S)-α-amino acid esters (8) with ketones (9) was achieved. The effects of solvents and the ester moiety of chiral reagents on the asymmetric induction were examined, and (S)-(+)-2-amino-3-phenylpropane (15a) was prepared from (S)-valine tert-butyl ester and phenylacetone in 63% yield and 87% optical yield. The possible steric course of the asymmetric hydrogenation is discussed. The reduction of the Schiff bases (10) with sodium borohydride is also described.

  通过催化加氢以及(S)-α-氨基酸酯(8)与酮(9)的希夫碱(10)的化学反式，实现了光学活性胺(15)的不对称合成。研究了溶剂和手性试剂的酯基对不对称诱导的影响，并以(S)-缬氨酸叔丁酯和苯丙酮为原料制备了(S)-(+)-2-氨基-3-苯基丙烷(15a)，产率为 63%，光学产率为 87%。讨论了不对称氢化过程中可能存在的立体过程。还介绍了用硼氢化钠还原希夫碱 (10) 的过程。
• WO2008/98151
  申请人：——

  公开号：——

  公开（公告）日：——
• The Synthesis and Resolution of alpha-o-Chlorobenzylethylamine¹
  作者：I. B. Johns、J. M. Burch

  DOI：10.1021/ja01271a045

  日期：1938.4
• EPC-Synthesis of functionalised amides via chiral β-nitrogenated organolithium compounds
  作者：Francisco Foubelo、Miguel Yus

  DOI：10.1016/0957-4166(96)00382-5

  日期：1996.10

  The deprotonation of chiral chloroamides or carbamates 1, 4, 7, 10, 13 and 16 with n-butyllithium followed by in situ lithiation with lithium naphthalenide, both at -78 degrees C in THF, leads to the formation of the corresponding chiral dianionic intermediates, which by reaction with different electrophiles [H2O, D2O, Me(2)S(2), (CH2)(5)CO, Bu(t)CHO, PhCHO, CO2, CO(OEt)(2), BrCH(2)CO(2)Et and DCC] at -78 to 20 degrees C affords, after hydrolysis with water, the expected enantiopure compounds. Copyright (C) 1996 Elsevier Science Ltd

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