(2S)-2-氨基-N-(4-甲氧基苯基)丙酰胺 | 65734-58-9

• 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
• 中文名称: (2S)-2-氨基-N-(4-甲氧基苯基)丙酰胺
• 英文名称: (S)-N'-(4-methoxyphenyl)alaninamide
• 英文别名: L-Ala-p-methoxyanilid；2-amino-N-(4-methoxyphenyl)propionamide；N-(4-Methoxyphenyl)-L-alaninamide；(2S)-2-amino-N-(4-methoxyphenyl)propanamide
• CAS: 65734-58-9
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: OUXHIQKKEDMJOC-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-氨基-N-(4-甲氧基苯基)丙酰胺 在 N-甲基吗啉 、 盐酸 、 DCE 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 naphth-1-oyl-Tza-Ala-NHPh(4-OMe)
  参考文献：
  名称：

  Discovery of potent and selective phenylalanine derived CCR3 receptor antagonists. Part 2

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00249-9
• 作为产物：
  描述：

  甲氧苯胺 在 叠氮磷酸二苯酯 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (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

文献信息

• Electron transfer-initiated asymmetric photocyclization of chiral auxiliary-substituted N-acyl-α-dehydro(1-naphthyl)alaninamides to the corresponding 3,4-dihydrobenzo[f]quinolinone derivatives
  作者：Kei Maekawa、Kanji Kubo、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tet.2005.09.042

  日期：2005.11

  olinone derivatives (2) in excess at rt, respectively. The magnitude of diastereomeric excess (de) was varied in the range of −5–26% for (R,S)-2 and 16–92% for (S,S)-2, depending on the chiral auxiliary and reaction temperature. The mechanism of asymmetric induction in the photocyclization process eventually affording diastereomeric 2 was discussed based on solvent, tertiary amine, chiral auxiliary

  在含有叔胺的甲醇中，标题为N-酰基-α-脱氢萘丙氨酰胺[（Z）-1 ]与（S）-1-苯基乙氨基和（S）-丙氨酰胺辅助基的光诱导电子转移反应显示形成（R，在室温下分别过量的S）-和（S，S）-3,4-二氢苯并[ f ]喹啉酮衍生物（2）。（R，S）-2的非对映体过量（de）的幅度在-5–26％的范围内，而（S，S）-的非对映体过量（de）的范围在16–92％的范围内2，取决于手性助剂和反应温度。基于溶剂，叔胺，手性助剂和温度对de值的影响以及非对映体烯醇中间体的MM2和PM5计算，讨论了最终提供非对映体2的光环化过程中的不对称诱导机理。
• Amino Acid Amide based Ionic Liquid as an Efficient Organo-Catalyst for Solvent-free Knoevenagel Condensation at Room Temperature
  作者：Pralhad A. Burate、Balasaheb R. Javle、Pranjal H. Desale、Anil K. Kinage

  DOI：10.1007/s10562-019-02840-5

  日期：2019.9

  Ionic liquids of amino acid amide were synthesized and used as an efficient catalyst for solvent-free Knoevenagel condensation. Synthesized ionic liquids are an environmentally benign, inexpensive, metal free and plays the dual role of solvent as well as an efficient catalyst for Knoevenagel condensation. A wide range of aliphatic, aromatic and heteroaromatic aldehydes easily undergo condensation with

  合成了氨基酸酰胺离子液体，并将其用作无溶剂 Knoevenagel 缩合的有效催化剂。合成的离子液体是一种环境友好、价格低廉、不含金属的物质，既是溶剂又是 Knoevenagel 缩合的有效催化剂。多种脂肪族、芳香族和杂芳香族醛很容易与丙二腈和氰基乙酸乙酯缩合。该反应在室温下进行，无需使用任何有机溶剂，反应速度非常快，收率非常好。此外，该催化剂易于分离和回收而不会损失活性。Graphic Abstract
• Discrimination of enantiomers of amides with two stereogenic centers enabled by chiral bisthiourea derivatives using ¹H NMR spectroscopy
  作者：Hanchang Zhang、Hongmei Zhao、Jie Wen、Zhanbin Zhang、Pericles Stavropoulos、Yanlin Li、Lin Ai、Jiaxin Zhang

  DOI：10.1039/d1ob00742d

  日期：——

  chiral discriminating results towards most amides with two stereogenic centers, which have been rarely studied as chiral substrates by 1H NMR spectroscopy. In particular, CSAs 7, 8 and 9, featuring 3,5-bis(trifluoromethyl)benzene residues, exhibit outstanding chiral discriminating capabilities towards all amides, providing well-separated 1H NMR signals and sufficiently large nonequivalent chemical shifts

  一些含有两个立体中心的新型酰胺的对映体衍生自D-和L -α-氨基酸作为客体，通过1 H NMR 光谱进行手性识别。催化不对称合成产物、天然产物或其全合成产物、手性药物中常存在多种具有两个或多个立体中心的手性酰胺。探索它们的手性识别将是一项具有挑战性且有意义的工作。为此，由(1 S ,2 S )-(+)-1,2-二氨基环己烷、 D -α-氨基酸和异硫氰酸酯作为手性溶剂合成了一类新型手性双硫脲衍生物1-9 （国家安全局）。事实证明，CSAs 1-9对大多数具有两个立构中心的酰胺具有更好的手性辨别结果，而这些酰胺很少作为手性底物通过1 H NMR 光谱进行研究。特别是，具有 3,5-双（三氟甲基）苯残基的 CSA 7 、 8和9 ，对所有酰胺表现出出色的手性辨别能力，提供良好分离的1 H NMR 信号和足够大的非等价化学位移。为了测试它们在测定对映体过量方面的实际应用，分别在 CSA 7和8存在下测量了不同光学纯度的手性酰胺
• 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 a Phosphodiesterase 9A Inhibitor as a Potential Hypoglycemic Agent
  作者：Yong-xian Shao、Manna Huang、Wenjun Cui、Ling-Jun Feng、Yinuo Wu、Yinghong Cai、Zhe Li、Xinhai Zhu、Peiqing Liu、Yiqian Wan、Hengming Ke、Hai-Bin Luo

  DOI：10.1021/jm500836h

  日期：2014.12.26

  Phosphodiesterase 9 (PDE9) inhibitors have been studied as potential therapeutics for treatment of diabetes and Alzheimers disease. Here we report a potent PDE9 inhibitor 3r that has an IC50 of 0.6 nM and >150-fold selectivity over other PDEs. The HepG2 cell-based assay shows that 3r inhibits the mRNA expression of phosphoenolpyruvate carboxykinase and glucose 6-phosphatase. These activities of 3r, together with the reasonable pharmacokinetic properties and no acute toxicity at 1200 mg/kg dosage, suggest its potential as a hypoglycemic agent. The crystal structure of PDE9-3r reveals significantly different conformation and hydrogen bonding pattern of 3r from those of previously published 28s. Both 3r and 28s form a hydrogen bond with Tyr424, a unique PDE9 residue (except for PDE8), but 3r shows an additional hydrogen bond with Ala452. This structure information might be useful for design of PDE9 inhibitors.