N-(N-(tert-butoxycarbonyl)-L-alanyl)-4-methoxyaniline | 269064-59-7

• 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: N-(N-(tert-butoxycarbonyl)-L-alanyl)-4-methoxyaniline
• 英文别名: (S)-tert-butyl (1-((4-methoxyphenyl)amino)-1-oxopropan-2-yl)carbamate；4-methoxyphenylamino-Ala-Boc；[1-(4-methoxyphenylcarbamoyl)ethyl]carbamic acid tert-butyl ester；tert-butyl N-[(2S)-1-(4-methoxyanilino)-1-oxopropan-2-yl]carbamate
• CAS: 269064-59-7
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: JDALLHFGWLOPEA-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(N-(tert-butoxycarbonyl)-L-alanyl)-4-methoxyaniline 在 三氟乙酸 作用下， 反应 2.0h， 以100%的产率得到(2S)-2-氨基-N-(4-甲氧基苯基)丙酰胺
  参考文献：
  名称：

  Design and Synthesis of Small Molecules Based on a Substructural Analysis of the Histone Deacetylase Inhibitors TSA and SAHA

  摘要：

  组织脱乙酰化酶（HDACs）抑制剂是诱导分化的专利诱导剂，具有作为化学预防和治疗癌症药物的巨大潜力。在这篇论文中，我们研究了三种合成抑制剂A1a、b，A2a。类似物混合物三种曲古司汀A（TSA）、硝酰苯基羟基甲酸SAHA，以寻找新的组织脱乙酰化酶（HDACs）抑制剂。

  DOI：

  10.1155/2011/403129
• 作为产物：
  描述：

  甲氧苯胺 、 (2S)-2-({[(2-甲基-2-丙基)氧基]羰基}氨基)硫代丙S-酸 在 9-mesityl-10-methylacridinium tetrafluoroborate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以82%的产率得到N-(N-(tert-butoxycarbonyl)-L-alanyl)-4-methoxyaniline
  参考文献：
  名称：

  可见光诱导的酰胺键形成。

  摘要：

  在有机光氧化还原催化剂下开发了无金属，无碱和无添加剂的酰胺键形成反应。这种绿色方法显示出优异的功能选择性，而不会影响其他功能基团，例如醇，酚，醚，酯，卤素或杂环。该方法具有广泛的底物范围，与水和空气的良好相容性以及高产率（≤95％）。通过合成重要的药物分子（例如对乙酰氨基酚，褪黑激素，吗氯贝胺和乙酰唑胺）证明了其潜在的实用性。

  DOI：

  10.1021/acs.orglett.9b03905

文献信息

• One-pot mechanosynthesis of aromatic amides and dipeptides from carboxylic acids and amines
  作者：Vjekoslav Štrukil、Boris Bartolec、Tomislav Portada、Ivica Đilović、Ivan Halasz、Davor Margetić

  DOI：10.1039/c2cc36613d

  日期：——

  Environmentally friendly one-pot synthesis of amides, bis-amides and dipeptides by mechanochemical carbodiimide-mediated coupling of carboxylic acids and amines is described; high reaction yields and simple aqueous work-up allow for the clean, practical and fast preparation of a variety of compounds containing the amide bond from readily accessible reagents.

  通过机械化学碳二亚胺介导的羧酸和胺的偶联，描述了环境友好的一锅合成酰胺，双酰胺和二肽。高反应产率和简单的水后处理使得可以从容易获得的试剂中清洁，实用，快速地制备各种含有酰胺键的化合物。
• Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes
  作者：Fubin Chen、Shi Huang、Hui Zhang、Fengying Liu、Yungui Peng

  DOI：10.1016/j.tet.2008.07.051

  日期：2008.9

  A series of proline-based dipeptide organocatalysts with two amide units (1-16) have been developed and evaluated in the direct catalytic asymmetric aldol reactions of aldehydes with cyclohexanone. These catalysts showed good solubility in organic solvents compared with their corresponding carboxyl terminal dipeptides. The robust amide bond formation allowed structural modifications and fine tuning of catalyst properties by varying the stereo and electronic effects of the terminal amide to affect the ability of hydrogen bonding formation between the catalysts and the substrates. The reactions proceeded smoothly in high yields (up to 99%), enantioselectivities (up to 98% ee) and anti-diastereoselectivities (up to 99:1) in the presence of bifunctional organocatalyst 4 under the optimal reaction conditions. (C) 2008 Elsevier Ltd, All rights reserved.
• Discovery of potent and selective phenylalanine derived CCR3 receptor antagonists. Part 2
  作者：Dashyant Dhanak、Lisa T Christmann、Michael G Darcy、Richard M Keenan、Steven D Knight、Judithann Lee、Lance H Ridgers、Henry M Sarau、Dinubhai H Shah、John R White、Lily Zhang

  DOI：10.1016/s0960-894x(01)00249-9

  日期：2001.6

  Highly potent CCR3 antagonists have been developed from a previously reported series of phenylalanine ester-based leads. Solution-phase, parallel synthesis optimization was utilized to identify highly potent, functional CCR3 antagonists. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Pronounced Self‐Induced Diastereomeric Anisochronism in Anisidine Amino Acid Diamides
  作者：Jan-Michael Menke、Oliver Trapp

  DOI：10.1002/chem.202400623

  日期：——

  The emergent properties resulting from selective supramolecular interactions are of significant importance for materials and chemical systems. For the directed use of such properties, a fundamental understanding of the interaction mechanism and the resulting mode of function is necessary for a tailored design. The self‐induced diastereomeric anisochronism effect (SIDA), which occurs in the intermolecular interaction of chiral molecules, generates unique properties such as chiral self‐recognition and nonlinear effects. Here we show that anisidine amino acid diamides lead to extraordinary signal splitting in NMR spectra through supramolecular interaction and homochiral self‐recognition. By systematic experiments we have investigated the underlying SIDA effect, explored its limits and finally successfully utilized it in the determination of enantiomeric ratios by NMR spectroscopy of chiral ‘SIDA‐inactive’ compounds such as thalidomide.
• Visible Light-Induced Amide Bond Formation
  作者：Wangze Song、Kun Dong、Ming Li

  DOI：10.1021/acs.orglett.9b03905

  日期：2020.1.17

  A metal-, base-, and additive-free amide bond formation reaction was developed under an organic photoredox catalyst. This green approach showed excellent functional selectivity without affecting other functional groups such as alcohols, phenols, ethers, esters, halogens, or heterocycles. This method featured a broad substrate scope, good compatibility with water and air, and high yields (≤95%). The

  在有机光氧化还原催化剂下开发了无金属，无碱和无添加剂的酰胺键形成反应。这种绿色方法显示出优异的功能选择性，而不会影响其他功能基团，例如醇，酚，醚，酯，卤素或杂环。该方法具有广泛的底物范围，与水和空气的良好相容性以及高产率（≤95％）。通过合成重要的药物分子（例如对乙酰氨基酚，褪黑激素，吗氯贝胺和乙酰唑胺）证明了其潜在的实用性。