2-羟基-N-苯基丙酰胺 | 106942-22-7

• 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: 2-羟基-N-苯基丙酰胺
• 英文名称: lactanilide
• 英文别名: 2-Hydroxy-N-phenylpropionamide；2-Hydroxy-N-phenylpropanamide；2-hydroxypropananilide；2-hydroxypropanilide；N-phenyl lactamide
• CAS: 106942-22-7；125473-43-0；6252-10-4
• 化学式: C₉H₁₁NO₂
• mdl: MFCD00069045
• 分子量: 165.192
• InChiKey: NXHFPNVCAZMTSG-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  164 °C(Press: 2 Torr)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-羟基-N-苯基丙酰胺 在 十二羰基三钌 、 氨 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 24.0h， 以83%的产率得到丙酰胺,2-氨基-N-苯基-
  参考文献：
  名称：

  α-氨基酸酰胺的合成：α-羟基酰胺的钌催化胺化

  摘要：

  给我一个N：α-羟基酰胺与多种胺（包括苯胺，脂肪族伯仲胺和仲胺以及氨）的催化胺化反应产生了多种α-氨基酰胺（请参见方案）。在可商购的[Ru 3（CO）12 ] / DCPE催化剂体系存在下，这种高效原子化的胺化方案可以高效进行。

  DOI：

  10.1002/anie.201104309
• 作为产物：
  描述：

  2-氧代-N-苯基-丙酰胺 在 diethylzinc polymethylhydrosiloxane 、 N,N'-二苄基乙二胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.0h， 以99%的产率得到2-羟基-N-苯基丙酰胺
  参考文献：
  名称：

  Direct Zn–diamine promoted reduction of CO and CN bonds by polymethylhydrosiloxane in methanol

  摘要：

  在室温下，酮和亚胺在甲醇中通过使用聚甲基氢硅氧烷（PMHS）和简单的锌-胺催化剂，采用一步法化学选择性地还原为相应的醇和胺，并获得高产率。

  DOI：

  10.1039/b210144k

文献信息

• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• Efficient Copper(II)-Catalyzed Transamidation of Non-Activated Primary Carboxamides and Ureas with Amines
  作者：Min Zhang、Sebastian Imm、Sebastian Bähn、Lorenz Neubert、Helfried Neumann、Matthias Beller

  DOI：10.1002/anie.201108599

  日期：2012.4.16

  Amid(e) them all: Primary carboxamides and ureas react with aromatic and aliphatic amines in the presence of a copper catalyst to give a wide range of functionalized amides (see scheme).

  它们全都具有：伯羧酰胺和脲在铜催化剂的存在下与芳族和脂族胺反应，得到各种官能化的酰胺（请参阅方案）。
• Simultaneous Quantification of Metabolites Involved in Central Carbon and Energy Metabolism Using Reversed-Phase Liquid Chromatography−Mass Spectrometry and in Vitro ¹³C Labeling
  作者：Wen-Chu Yang、Miroslav Sedlak、Fred E. Regnier、Nathan Mosier、Nancy Ho、Jiri Adamec

  DOI：10.1021/ac801693c

  日期：2008.12.15

  Comprehensive analysis of intracellular metabolites is a critical component of elucidating cellular processes. Although the resolution and flexibility of reversed-phase liquid chromatography−mass spectrometry (RPLC−MS) makes it one of the most powerful analytical tools for metabolite analysis, the structural diversity of even the simplest metabolome provides a formidable analytical challenge. Here we describe a robust RPLC−MS method for identification and quantification of a diverse group of metabolites ranging from sugars, phosphosugars, and carboxylic acids to phosphocarboxylics acids, nucleotides, and coenzymes. This method is based on in vitro derivatization with a 13C-labeled tag that allows internal standard based quantification and enables separation of structural isomer pairs like glucose 6-phosphate and fructose 6-phosphate in a single chromatographic run. Calibration curves for individual metabolites showed linearity ranging over more than 2 orders of magnitude with correlation coefficients of R2 > 0.9975. The detection limits at a signal-to-noise ratio of 3 were below 1.0 μM (20 pmol) for most compounds. Thirty common metabolites involved in glycolysis, the pentose phosphate pathway, and tricarboxylic acid cycle were identified and quantified from yeast lysate with a relative standard deviation of less than 10%.

  详细分析细胞内代谢物是阐明细胞过程的关键组成部分。尽管反相液相色谱-质谱联用（RPLC-MS）的分辨率和灵活性使其成为代谢物分析中最强大的分析工具之一，但即使是简单的代谢组，其结构的多样性也带来了巨大的分析挑战。本文描述了一种稳健的RPLC-MS方法，用于鉴定和定量一系列广泛的代谢物，包括糖类、磷酸糖、羧酸、磷酸羧酸、核苷酸和辅酶。该方法基于使用13C标记标签的体外衍生化，允许基于内标的定量，并能在单次色谱运行中分离结构异构体对，如葡萄糖6-磷酸和果糖6-磷酸。单个代谢物的校准曲线显示线性范围超过两个数量级，相关系数R² > 0.9975。大多数化合物的信噪比为3的检测限低于1.0 μM（20 pmol）。从酵母裂解液中鉴定和定量了涉及糖酵解、戊糖磷酸途径和三羧酸循环的30种常见代谢物，相对标准偏差小于10%。
• NON-STEROIDAL ANTIANDROGENS AND SELECTIVE ANDROGEN RECEPTOR MODULATORS WITH A PYRIDYL MOIETY
  申请人：LABRIE Fernand

  公开号：US20150175576A1

  公开（公告）日：2015-06-25

  Compounds having the structure or their salts: are used to treat or reduce the likelihood of acquiring androgen-dependent diseases, such as prostate cancer, benign prostatic hyperplasia, polycystic ovarian syndrome, acne, hirsutism, seborrhea, androgenic alopecia, male baldness, muscle atrophy and weakness, sarcopenia, male hypogonadism, erectile dysfunction, female sexual dysfunction and osteoporosis. They can be formulated together with pharmaceutically acceptable diluent or carrier or otherwise made into any pharmaceutical dosage form. Combinations with other active pharmaceutical agents are also disclosed.

  具有以下结构或其盐的化合物：用于治疗或减少患雄激素依赖性疾病的可能性，如前列腺癌、良性前列腺增生、多囊卵巢综合征、痤疮、多毛症、皮脂溢、雄激素性脱发、男性秃头、肌肉萎缩和无力、肌肉质量减少、男性性腺功能减退、勃起功能障碍、女性性功能障碍和骨质疏松症。它们可以与药学上可接受的稀释剂或载体一起配制，或以任何药物剂量形式制成。还披露了与其他活性药物成分的组合。
• A General and Efficient Copper Catalyst for the Amidation of Aryl Halides
  作者：Artis Klapars、Xiaohua Huang、Stephen L. Buchwald

  DOI：10.1021/ja0260465

  日期：2002.6.1

  was developed for the amidation of aryl halides by using 0.2-10 mol % of CuI, 5-20 mol % of a 1,2-diamine ligand, and K(3)PO(4), K(2)CO(3), or Cs(2)CO(3) as base. Catalyst systems based on N,N'-dimethylethylenediamine or trans-N,N'-dimethyl-1,2-cyclohexanediamine were found to be the most active even though several other 1,2-diamine ligands could be used in the easiest cases. Aryl iodides, bromides, and

  通过使用 0.2-10 mol% 的 CuI、5-20 mol% 的 1,2-二胺配体和 K(3)PO(4), K (2)CO(3) 或 Cs(2)CO(3) 作为碱。发现基于 N,N'-二甲基乙二胺或反式-N,N'-二甲基-1,2-环己二胺的催化剂体系是最活跃的，尽管在最简单的情况下可以使用其他几种 1,2-二胺配体。芳基碘化物、溴化物，在某些情况下甚至芳基氯化物都可以有效地酰胺化。反应中可以容忍多种官能团，包括许多与 Pd 催化的酰胺化或胺化方法不兼容的官能团。