(S)-N-(benzyloxycarbonyl)valinanilide | 16876-74-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-(benzyloxycarbonyl)valinanilide
• 英文别名: benzyl (S)-N-(2-methyl-1-phenylcarbamoylpropyl)carbamate；(S)-benzyl (3-methyl-1-oxo-1-(phenylamino)butan-2-yl)carbamate；benzyl (S)-(3-methyl-1-oxo-1-(phenylamino)butan-2-yl)carbamate；Cbz-L-Val-NHPh；N-benzyloxycarbonyl-L-valine anilide；N-Benzyloxycarbonyl-L-valin-anilid；N-(N'-Benzyloxycarbonyl-valinyl)-anilin；Benzyloxycarbonyl-Val-anilid；N-Phenyl L-Z-Valinamide；benzyl N-[(2S)-1-anilino-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 16876-74-7
• 化学式: C₁₉H₂₂N₂O₃
• 分子量: 326.395
• InChiKey: FNZWOLATMXPENQ-KRWDZBQOSA-N

物化性质

• 熔点：
  182-184 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  544.0±43.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(benzyloxycarbonyl)valinanilide 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 碘 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide

  摘要：

  A Pd-catalyzed enantio selective synthesis of quaternary alpha-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic beta-keto esters with a nitrogen functional group at the alpha-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary alpha-amino acid derivatives in excellent yield and in up to 92% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.020
• 作为产物：
  描述：

  CBZ-L-缬氨酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 (S)-N-(benzyloxycarbonyl)valinanilide
  参考文献：
  名称：

  饥饿条件下贝克酵母生物催化水解各种含 L-苯丙氨酸的苯胺

  摘要：

  在中性条件下，在不含蔗糖的情况下，使用贝克酵母对各种含有l-苯丙氨酸的苯胺的生物催化水解有效地进行，以 26-60% 的产率提供相应的苯胺衍生物。

  DOI：

  10.1016/j.tetlet.2022.154130

文献信息

• Organocatalysis of asymmetric aldol reaction in water: comparison of catalytic properties of (S)-valine and (S)-proline amides
  作者：A. S. Kucherenko、D. E. Siyutkin、R. R. Dashkin、S. G. Zlotin

  DOI：10.1007/s11172-013-0132-z

  日期：2013.4

  (S)-Valine amides containing (S)- or (R)-α-phenylethyl substituents at N1 atom efficiently catalyze asymmetric aldol reactions between cyclic (heterocyclic) ketones and aromatic aldehydes in water, predominantly giving rise to the aldol anti-diastereomers in high yields (up to 98%) and enantiomeric excess (up to 94%).

  含有在N1原子上带有(S)-或(R)-α-苯乙基取代基的(S)-缬氨酰胺，能高效催化水中环状（杂环）酮与芳香醛的不对称Aldol反应，主要生成高产率（高达98%）和高对映体过量（高达94%）的Aldol反式异构体。
• Fast Amide Couplings in Water: Extraction, Column Chromatography, and Crystallization Not Required
  作者：Sudripet Sharma、Nicklas W. Buchbinder、Wilfried M. Braje、Sachin Handa

  DOI：10.1021/acs.orglett.0c01676

  日期：2020.8.7

  In the micelle of PS-750-M, the presence of 3 degrees amides from the surfactant proline linker mimics dimethylforma-mide, dimethylacetamide, and N-methyl-2-pyrrolidone. The resultant micellar properties enable extremely fast amide couplings mediated by 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (without hydroxybenzotriazole), rather than expensive and specialized coupling agents. Conditions have been developed wherein products precipitate, and isolation by filtration completely avoids the use of organic solvent. This methodology is scalable and avoids product epimerization.
• Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides
  作者：Jorge Escorihuela、M. Isabel Burguete、Santiago V. Luis

  DOI：10.1016/j.tetlet.2008.09.120

  日期：2008.11

  A series of alpha-amino amides derived from natural amino acids (alanine, valine, phenylalanine, isoleucine, and phenylglycine) have been synthesized and fully characterized. Their Ni(II) complexes prepared from Ni(acac)(2) catalyze the enantioselective conjugate addition of diethylzinc to chalcones in high yields and in good enantioselectivities (up to 84%). The side chain of the amino acid and the substituents in the amide nitrogen govern the enantioselectivity of the catalytic process. (c) 2008 Elsevier Ltd. All rights reserved.
• 10.1021/ol403508
  作者：Bai, Jianfei、Zambron, Bartosz K.、Vogel, Pierre

  DOI：10.1021/ol403508

  日期：——
• Falorni, Massimo; Lardicci, Luciano; Giacomelli, Giampaolo, Gazzetta Chimica Italiana, 1988, vol. 118, # 8, p. 573 - 576
  作者：Falorni, Massimo、Lardicci, Luciano、Giacomelli, Giampaolo

  DOI：——

  日期：——