N-methyl-N-phenyl-α-hydroxypropanamide | 5455-67-4

• 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: N-methyl-N-phenyl-α-hydroxypropanamide
• 英文别名: 2-hydroxy-N-methyl-N-phenylpropanamide；N-methyl-lactanilide；N-Methyl-lactanilid；Milchsaeure-methylanilid；2-hydroxypropionic acid N-methylanilide
• CAS: 5455-67-4
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD19347585
• 分子量: 179.219
• InChiKey: YOZNZNZSJNNALS-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  290.1±23.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-N-phenyl-α-hydroxypropanamide 、 4-chloro-2-methoxy-1,8-naphthyridine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 二甲基亚砜 为溶剂， 反应 4.5h， 以33%的产率得到2-(2-methoxy-1,8-naphthyridin-4-yloxy)-N-methyl-N-phenylpropanamide
  参考文献：
  名称：

  Translocator protein ligands based on N -methyl-(quinolin-4-yl)oxypropanamides with properties suitable for PET radioligand development

  摘要：

  Modifications to an N-methyl-(quinolin-4-yl)oxypropanamide scaffold were explored to discover leads for developing new radioligands for PET imaging of brain TSPO (translocator protein), a biomarker of neuroinfiammation. Whereas contraction of the quinolinyl portion of the scaffold or cyclization of the tertiary amido group abolished high TSPO affinity, insertion of an extra nitrogen atom into the 2-arylquinolinyl portion was effective in retaining sub-nanomolar affinity for rat TSPO, while also decreasing lipophilicity to within the moderate range deemed preferable for a PET radioligand. Replacement of a phenyl group on the amido nitrogen with an isopropyl group was similarly effective. Among others, compound 20 (N-methyl-N-phenyl-2-[2-(pyridin-2-yl)-1,8-naphthyridin-4-yloxy]propanamide) appears especially appealing for PET radioligand development, based on high selectivity and high affinity (K-i = 0.5 nM) for rat TSPO, moderate lipophilicity (logD = 2.48), and demonstrated amenability to labeling with carbon-11. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2016.08.046
• 作为产物：
  描述：

  N-甲基苯胺 在 4-二甲氨基吡啶 、 三乙基硼 、 氧气 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 21.25h， 生成 N-methyl-N-phenyl-α-hydroxypropanamide
  参考文献：
  名称：

  Efficient Radical Oxygenation of α-Iodocarboxylic Acid Derivatives

  摘要：

  [GRAPHICS]Treatment of alpha-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding a-hydroxy acid derivatives. This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of triethylborane and oxygen, with the alpha-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimination product is observed, tertiary iodides are efficiently converted to alcohols, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.

  DOI：

  10.1021/ol990971n

文献信息

• FORUMLATIONS
  申请人：Bell Gordon Alastair

  公开号：US20090227453A1

  公开（公告）日：2009-09-10

  This invention relates to the use of lactamide compounds of formula (I): CH 3 CH(OH)C(═O)NR 1 R 2 , where R 1 and R 2 are each independently hydrogen; or C 1-6 alkyl, C 2-6 alkenyl or C 3-6 cycloalkyl, each of which is optionally substituted by up to three substituents independently selected from phenyl, hydroxy, C 1-5 alkoxy, morpholinyl and NR 3 R 4 where R 3 and R 4 are each independently C 1-3 alkyl; or phenyl optionally substituted by up to three substituents independently selected from C 1-3 alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, piperidinyl or azepanyl ring, each of which is optionally substituted by up to three substituents independently selected from C 1-3 alkyl, in formulations to reduce the toxicity associated with other formulation components; to the use of certain lactamide compounds as solvents, especially in formulations, particularly in agrochemical formulations and in environmentally friendly formulations; to novel lactamide compounds; and to processes for preparing lactamide compounds.

  这项发明涉及使用式（I）的乳酰胺化合物：CH3CH(OH)C(═O)NR1R2，其中R1和R2分别独立地是氢；或C1-6烷基，C2-6烯基或C3-6环烷基，每种基团可选择地被最多三个取代基取代，这些取代基独立地选自苯基、羟基、C1-5烷氧基、吗啉基和NR3R4，其中R3和R4分别独立地是C1-3烷基；或苯基可选择地被最多三个取代基取代，这些取代基独立地选自C1-3烷基；或R1和R2与它们连接的氮原子一起形成吗啉基、吡咯啉基、哌啶基或氮杂环庚基环，每种环可选择地被最多三个取代基取代，这些取代基独立地选自C1-3烷基，在配方中减少与其他配方成分相关的毒性；使用某些乳酰胺化合物作为溶剂，特别是在配方中，尤其是在农药配方和环保配方中；新型乳酰胺化合物；以及制备乳酰胺化合物的方法。
• Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-<i>N</i>-arylamides under an Oxygen Atmosphere
  作者：Shunsuke Chiba、Line Zhang、Jian-Yuan Lee

  DOI：10.1021/ja1027327

  日期：2010.6.2

  copper-catalyzed reaction of alpha-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from alpha-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C=O bonds. The

  发现α-叠氮基-N-芳基酰胺的铜催化反应在氧气氛下进行以提供氮杂螺环己二烯酮。本转化是通过从 α-叠氮基-N-芳基酰胺脱氮形成亚胺基铜物种以及它们与酰胺氮上的分子内苯环的亚氨基铜化，然后连续形成 C=O 键来进行的。初步调查显示，分子氧是实现本催化环化的先决条件，并且发现 O(2) 的氧原子之一被纳入环己二烯酮部分。
• Photochemical Deoxygenative Hydroalkylation of Unactivated Alkenes Promoted by a Nucleophilic Organocatalyst
  作者：Jadab Majhi、Bianca Matsuo、Hyunjung Oh、Saegun Kim、Mohammed Sharique、Gary A. Molander

  DOI：10.1002/anie.202317190

  日期：2024.2.5

  A new photochemical method for deoxygenative hydroalkylation of a wide range of alkenes and lactic acid derivatives is reported. This approach utilizes thiophenol as a nucleophilic organic catalyst which forms the key intermediate of this transformation via an SN2 process.

  报道了一种用于多种烯烃和乳酸衍生物脱氧加氢烷基化的新光化学方法。该方法利用苯硫酚作为亲核有机催化剂，通过 S N 2 过程形成该转化的关键中间体。
• Bischoff; Walden, Justus Liebigs Annalen der Chemie, 1894, vol. 279, p. 123
  作者：Bischoff、Walden

  DOI：——

  日期：——
• Pohmakotr, Manat; Winotai, Chanchai, Synthetic Communications, 1988, vol. 18, # 16-17, p. 2141 - 2146
  作者：Pohmakotr, Manat、Winotai, Chanchai

  DOI：——

  日期：——