2(R)-N-(tert-butoxycarbonyl)-N'-methoxy-N'-methylphenylglycinamide | 819796-91-3

• 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: 2(R)-N-(tert-butoxycarbonyl)-N'-methoxy-N'-methylphenylglycinamide
• 英文别名: (R)-N-Boc-N'-methyl-N'-methoxy-2-phenylglycinamide；tert-butyl N-[(1R)-2-[methoxy(methyl)amino]-2-oxo-1-phenylethyl]carbamate
• CAS: 819796-91-3
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: YSHFHFQXCUVLDX-GFCCVEGCSA-N

物化性质

• 密度：
  1.125±0.06 g/cm3(Predicted)

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：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2(R)-N-(tert-butoxycarbonyl)-N'-methoxy-N'-methylphenylglycinamide 在 苯甲醚 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-2-methyl-N-(2-oxo-1,2-diphenylethyl)propane-2-sulfonamide
  参考文献：
  名称：

  Stille Coupling of Stereochemically Defined α-Sulfonamidoorganostannanes

  摘要：

  Addition of tributylstannylmetallics to (R)-tert-butanesulfonimine derivatives of arylaldehydes provides alpha-sulfinamidostannanes with high (>98% de) diastereoselectivities. Oxidation of these compounds with m-CPBA gives alpha-sulfonamidostannanes which undergo Pd/Cu-catalyzed Stille-type couplings with benzoyl chloride. Best yields are achieved using the electron-rich tris(2,4,6-trimethoxyphenyl)phosphine as the ligand. Inversion of configuration at the benzylic carbon is observed.

  DOI：

  10.1021/ja044354s
• 作为产物：
  描述：

  左旋苯甘氨酸 在 sodium carbonate 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 2(R)-N-(tert-butoxycarbonyl)-N'-methoxy-N'-methylphenylglycinamide
  参考文献：
  名称：

  Stille Coupling of Stereochemically Defined α-Sulfonamidoorganostannanes

  摘要：

  Addition of tributylstannylmetallics to (R)-tert-butanesulfonimine derivatives of arylaldehydes provides alpha-sulfinamidostannanes with high (>98% de) diastereoselectivities. Oxidation of these compounds with m-CPBA gives alpha-sulfonamidostannanes which undergo Pd/Cu-catalyzed Stille-type couplings with benzoyl chloride. Best yields are achieved using the electron-rich tris(2,4,6-trimethoxyphenyl)phosphine as the ligand. Inversion of configuration at the benzylic carbon is observed.

  DOI：

  10.1021/ja044354s

文献信息

• COMPOUNDS HAVING NPY Y5 RECEPTOR ANTAGONISTIC ACTIVITY
  申请人：Sakagami Masahiro

  公开号：US20110028468A1

  公开（公告）日：2011-02-03

  This invention provides a compound of the formula (I): a pharmaceutically acceptable salt or solvate thereof, wherein R 1 is substituted or unsubstituted alkyl or the like, R 2 is hydrogen or substituted or unsubstituted alkyl, Ring A is monocyclic or bicyclic aromatic heterocycle, R 3 is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted heterocycle, R 4 is halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl or the like, m is an integer between 0 and 2, n is an integer between 0 and 5, R is halogen, oxo, cyano, nitro, substituted or unsubstituted alkyl or the like, and p is an integer between 0 and 2 as novel compounds having NPY Y5 antagonistic activity.

  这项发明提供了式(I)的化合物： 其药学上可接受的盐或溶剂化合物， 其中 R1为取代或未取代的烷基或类似物， R2为氢或取代或未取代的烷基， 环A为单环或双环芳香杂环， R3为取代或未取代的芳基，取代或未取代的杂芳基或取代或未取代的杂环， R4为卤素，氰基，取代或未取代的烷基，取代或未取代的环烷基或类似物， m为0到2之间的整数， n为0到5之间的整数， R为卤素，氧代，氰基，硝基，取代或未取代的烷基或类似物，以及 p为0到2之间的整数 作为具有NPY Y5拮抗活性的新化合物。
• Preparation of α-Hydroxy-β-Fmoc Amino Acids from N-Boc Amino Acids
  作者：Christopher Teleha、Erik Johnson、M. Hubieki、Andrew Combs

  DOI：10.1055/s-0031-1289586

  日期：2011.12

  A general method for the conversion of N-Boc amino acids­ into their homologated α-hydroxy-β-Fmoc amino acids is described. The protocol involved preparation of the amino aldehyde by reduction of the corresponding Weinreb amides, hydrocyanation, and hydrolysis of the nitrile group, followed by reprotection of the amino acid as the Fmoc derivative. N-Boc amino acid - reduction - hydrocyanation - N-Fmoc

  描述了将N -Boc氨基酸转化为其同源的α-羟基-β-Fmoc氨基酸的一般方法。该方案涉及通过还原相应的Weinreb酰胺，氢氰化和腈基水解来制备氨基醛，然后将氨基酸作为Fmoc衍生物重新保护。 N -Boc氨基酸-还原-氢氰化-N -Fmoc氨基酸
• Design and synthesis of 7-membered lactam fused hydroxypyridinones as potent metal binding pharmacophores (MBPs) for inhibiting influenza virus PAN endonuclease
  作者：Lei Zhang、Di Ke、Yuting Li、Hui Zhang、Xi Zhang、Sihan Wang、Shaokai Ni、Bo Peng、Huixuan Zeng、Tingjun Hou、Yushen Du、Peichen Pan、Yongping Yu、Wenteng Chen

  DOI：10.1016/j.ejmech.2024.116639

  日期：2024.10

  Moreover, (R, S)-16s demonstrated a potent anti-IAV efficacy (EC50 = 0.134 ± 0.093 μM) and weak cytotoxicity (CC50 = 15.35 μM), indicating the high selectivity of (R, S)-16s. Although the lead compound (R, S)-16s exhibited a little weaker activity than baloxavir, these findings illustrated the utility of a metal coordination-based strategy in generating novel MBPs with potent anti-influenza activity.

  由于流感病毒 RNA 聚合酶亚基 PAN 是一种双核 Mn2+ 依赖性核酸内切酶，因此具有 Mn2+ 配位的金属结合药效团 （MBP） 已被阐明为开发用于流感治疗的 PAN 抑制剂的一种有前途的策略。然而，很少有人关注 MBP 中供体原子的最佳排列与抗甲型流感病毒 （IAV） 疗效之间的关系。鉴于此，设计并合成了融合具有不同侧链、手性中心或环状系统的七元内酰胺环的特权羟基吡啶酮。构效关系研究产生命中化合物 16l （IC50 = 2.868 ± 0.063 μM对抗 IAV 聚合酶），其七元内酰胺环融合一个吡咯烷环。进一步优化 16l 上的疏水结合基团得到了先导化合物 （R， S）-16s，其对 IAV 聚合酶的抑制活性提高了 64 倍 （IC50 = 0.045 ± 0.002 μM）。此外，（R， S）-16s 表现出有效的抗 IAV 功效 （EC50 = 0.134 ± 0.093 μM）
• Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α-Amino Acids
  作者：Jason E. Hein、Laina M. Geary、Ashley A. Jaworski、Philip G. Hultin

  DOI：10.1021/jo051696n

  日期：2005.11.1

  A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral a-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.
• EP2280000
  申请人：——

  公开号：——

  公开（公告）日：——