(4S)-3-<3-(p-biphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone | 169894-53-5

• 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: (4S)-3-<3-(p-biphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone
• 英文别名: (4S)-3-[3-(4-phenylphenyl)propanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 169894-53-5
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: KNPKUIWTYUVSTP-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-3-<3-(p-biphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone 在 palladium on activated charcoal N-甲基吗啉 、 正丁基锂 、 三氯化铝 、 二甲基硫 、 氢气 、 四氯化钛 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 生成 (S)-5-Biphenyl-4-yl-4-(carboxymethyl-carbamoyl)-pentanoic acid
  参考文献：
  名称：

  Potent inhibitors of neutral endopeptidase. 2-Biphenyl- methylglutaric acid amide derivatives

  摘要：

  A series of glutaric acid amide derivatives were synthesized and tested for NEP inhibitory activity, Compounds 14a, 14b, 16a and 22, with a biphenylmethyl group at P-1 position, showed potent inhibitory activity,

  DOI：

  10.1016/0960-894x(95)00551-4
• 作为产物：
  描述：

  N-lithio-(4S)-4-isopropyl-2-oxazolidone 、 3-([1,1′-biphenyl]-4-yl)propanoyl chloride 以86%的产率得到(4S)-3-<3-(p-biphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone
  参考文献：
  名称：

  非对映选择性钯（0）催化的手性N-酰基氧杂唑烷酮的烯醇锂的反应。2-取代的（E）-4-亚烷基戊二酸二酯的不对称合成

  摘要：

  钯（0）烯醇化物锂催化的的反应1的Ñ与3-乙酰氧基-2- methylenealkanoates -acyloxazolidinones 2，通过容易地制备DABCO催化对应与丙烯酸酯的醛的联接，非对映选择性进行，并且区域选择性，得到手性ñ - [（E）-4-烷氧基羰基-4-戊烯基]恶唑烷酮3，金属肽酶抑制剂的有用中间体。

  DOI：

  10.1016/0040-4039(95)01043-h

文献信息

• Synthesis and evaluation of 2-(biphenylmethyl)glutaric acid amide derivatives as neutral endopeptidase inhibitors.
  作者：Hideyuki Kanno、Ken Osanai、Tatsuya Nishi、Minoru Iino、Shin-ichi Katakura、Taketoshi Furugohri、Yoshifumi Watanabe

  DOI：10.1016/s0960-894x(96)00255-7

  日期：1996.7

  A series of 2-(biphenylmethyl)glutaric acid amide derivatives were synthesized and evaluated for NEP inhibitory activity. The mode of inhibitor-enzyme interactions of the most potent compound 3a, with a thiazolylacetic acid group at the P-2' position, was evaluated by a computer analysis. Copyright (C) 1996 Elsevier Science Ltd
• Potent inhibitors of neutral endopeptidase. 2-Biphenyl- methylglutaric acid amide derivatives
  作者：Hideyuki Kanno、Ken Osanai、Taketoshi Furugohri、Yoshifumi Watanabe

  DOI：10.1016/0960-894x(95)00551-4

  日期：1996.1

  A series of glutaric acid amide derivatives were synthesized and tested for NEP inhibitory activity, Compounds 14a, 14b, 16a and 22, with a biphenylmethyl group at P-1 position, showed potent inhibitory activity,
• Diastereoselective palladium(0)-catalyzed reactions of lithium enolates of chiral N-acyloxazolidinones. Asymmetric synthesis of 2-substituted (E)-4-alkylidenepentanedioates
  作者：Hideyuki Kanno、Ken Osanai

  DOI：10.1016/0040-4039(95)01043-h

  日期：1995.7

  The palladium(0)-catalyzed reactions of lithium enolates 1 of N-acyloxazolidinones with 3-acetoxy-2-methylenealkanoates 2, easily prepared via DABCO-catalyzed coupling of corresponding aldehydes with acrylates, proceeded diastereoselectively and regioselectively to give chiral N-[(E)-4-alkoxycarbonyl-4-pentenoyl]oxazolidinones3, useful intermediates of metallopeptidase inhibitors.

  钯（0）烯醇化物锂催化的的反应1的Ñ与3-乙酰氧基-2- methylenealkanoates -acyloxazolidinones 2，通过容易地制备DABCO催化对应与丙烯酸酯的醛的联接，非对映选择性进行，并且区域选择性，得到手性ñ - [（E）-4-烷氧基羰基-4-戊烯基]恶唑烷酮3，金属肽酶抑制剂的有用中间体。