N-<(S)-α-methylbenzyl>pyruvamide | 77855-48-2

• 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-<(S)-α-methylbenzyl>pyruvamide
• 英文别名: 2-oxo-N-[(1S)-1-phenylethyl]propanamide
• CAS: 77855-48-2
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: CLVUSQHCRYUHIP-QMMMGPOBSA-N

物化性质

• 熔点：
  76-77 °C
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<(S)-α-methylbenzyl>pyruvamide 以100%的产率得到
  参考文献：
  名称：

  HARADA KAORU; MUNEGUMI TORATANE; NOMOTO SHINYA, TETRAHEDRON LETT., 1981, 22, NO 2, 111-114

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 丙酮酸 以16%的产率得到
  参考文献：
  名称：

  MUNEGUMI, TORATANE;HARADA, KAORU, BULL. CHEM. SOC. JAP., 1983, 56, N 1, 298-301

  摘要：

  DOI：

文献信息

• Selective amidation by a photocatalyzed umpolung reaction
  作者：Debasish Ghosh、Rajesh Nandi、Saikat Khamarui、Sukla Ghosh、Dilip K. Maiti

  DOI：10.1039/c9cc01079c

  日期：——

  Herein, a metal-catalyzed organic transformation merged with another organophotocatalyst has been developed under mild conditions for the production of α-ketoamides.

  在此，已经开发了一种金属催化的有机转化，与另一种有机光催化剂在温和条件下结合，用于生产α-酮酰胺。
• Asymmetric Catalytic Hydrogenations of Chiral α-Keto Amides
  作者：Kaoru Harada、Toratane Munegumi

  DOI：10.1246/bcsj.57.3203

  日期：1984.11

  Asymmetric catalytic hydrogenations of chiral pyruvamides were carried out using palladium on charcoal (Pd-C) as a catalyst to give lactamides with the diastereoisomeric purities (d.p.) of up to 62%. It was found that there was a linear correlation between the d.p. and the dielectric constant of the solvents used in the hydrogenations of chiral pyruvamides. The results were explained by employing the

  使用钯炭 (Pd-C) 作为催化剂进行手性丙酮酰胺的不对称催化氢化，得到非对映异构体纯度 (dp) 高达 62% 的乳酰胺。发现在手性丙酮酰胺氢化中使用的溶剂的dp和介电常数之间存在线性相关性。利用螯合模型和底物分子中的苯基在催化剂上的吸附来解释结果。还检查了温度对产品 dp 的影响。手性苯甲酰甲酰胺的催化氢化也被进行以得到低dp，据推测，底物的螯合配合物不能与催化剂形成主要构象。
• Asymmetric hydrogenation of chiral pyruvamides
  作者：Kaoru Harada、Toratane Munegumi、Shinya Nomoto

  DOI：10.1016/0040-4039(81)80162-1

  日期：1981.1

  Asymmetric catalytic hydrogenations of three kinds of chiral pyruvamides were carried out using palladium on charcoal as a catalyst to give lactamides with diastereomeric ratios ranging from 76:24 to 98:2.

  以钯/炭为催化剂，对三种手性丙酮酰胺进行不对称催化加氢，制得非对映异构体比例为76:24至98：2的内酰胺。
• Asymmetric Catalytic Hydrogenations of Oximes and Benzylimino Derivatives of Chiral Pyruvamides
  作者：Toratane Munegumi、Kaoru Harada

  DOI：10.1246/bcsj.61.1425

  日期：1988.4

  Oximes and benzylimino derivatives of chiral pyruvamides were hydrogenated over palladium hydroxide on charcoal in several solvents. Oximes of pyruvamides containing (R)-α-ethylbenzylamine as a chiral source gave (S)-alanine in excess (up to 70% e.e.) through the hydrolyses of the hydrogenated products.

  手性丙酮酰胺的肟和苄亚氨基衍生物在氢氧化钯上在几种溶剂中在木炭上氢化。含有 (R)-α-乙基苄胺作为手性来源的丙酮酰胺肟通过氢化产物的水解产生过量的 (S)-丙氨酸（高达 70% ee）。
• Peptidomimetic protease inhibitors
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP1849797A2

  公开（公告）日：2007-10-31

  The present invention relates to peptidomimetic compounds useful as protease inhibitors (1), particularly as serine protease inhibitors and more particularly as hepatitis C NS3 protease inhibitors; intermediates thereto; their preparation including novel steroselective processes to intermediates. The invention is also directed to pharmaceutical compositions and to methods for using the compounds for inhibiting HCV protease or treating a patient suffering from an HCV infection or physiological condition related to the infection. Also provided are pharmaceutical combinations comprising, in addition to one or more HCV serine protease inhibitors, one or more interferons exhibiting anti-HCV activity and/or one or more compounds having anti HCV activity and a pharmaceutically acceptable carrier, and methods for treating or preventing a HCV infection in a patient using the compositions. The present invention is also directed to a kit or pharmaceutical pack for treating or preventing HCV infection in a patient.

  本发明涉及可用作蛋白酶抑制剂（1），特别是丝氨酸蛋白酶抑制剂，更特别是丙型肝炎 NS3 蛋白酶抑制剂的拟肽化合物；其中间体；其制备方法，包括制备中间体的新型立体选择性工艺。本发明还涉及药物组合物以及使用这些化合物抑制 HCV 蛋白酶或治疗 HCV 感染患者或与感染相关的生理状况的方法。本发明还提供了药物组合物，除一种或多种HCV丝氨酸蛋白酶抑制剂外，还包括一种或多种具有抗HCV活性的干扰素和/或一种或多种具有抗HCV活性的化合物和药学上可接受的载体，以及使用该组合物治疗或预防患者HCV感染的方法。本发明还涉及一种用于治疗或预防患者HCV感染的试剂盒或药包。