(4R)-5-[(4S)-4-benzyl-2-oxooxazolidin-3-yl]-4-methyl-5-oxopentanenitrile | 136546-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-5-[(4S)-4-benzyl-2-oxooxazolidin-3-yl]-4-methyl-5-oxopentanenitrile
• 英文别名: (R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentanenitrile；(4R)-5-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-methyl-5-oxopentanenitrile
• CAS: 136546-77-5
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: FLVXCAFWZVNTSZ-OCCSQVGLSA-N

物化性质

• 沸点：
  501.4±33.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  70.4
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R)-5-[(4S)-4-benzyl-2-oxooxazolidin-3-yl]-4-methyl-5-oxopentanenitrile 在 platinum(IV) oxide 、 氢气 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 16.0h， 生成 (R)-5-amino-2-methylpentanoic acid hydrochloride
  参考文献：
  名称：

  Conformationally restricted analogs of the direct thrombin inhibitor FM 19

  摘要：

  The serine protease thrombin plays several key roles in the clotting cascade within the hemostatic system, such as in fibrin formation and platelet activation. Thus, development of an inhibitor that binds to the enzyme's active site (a direct thrombin inhibitor) offers an approach for the treatment of thrombus-associated diseases. Previous structure-activity relationship studies originally based on the bradykinin breakdown product Arg-Pro-Pro-Gly-Phe (RPPGF) led to the development of lead compound FM 19 (D-Arg-Oic-Pro-D-Ala-Phe(p-Me)-NH2). The recently determined X-ray structure of FM 19 in the active site of thrombin has revealed sites of modification to potentially improve inhibition. In this study, we report the synthesis and biological characterization of nine peptides that replace only the D-Arg residue of the FM 19 sequence, investigating ways to add conformational restriction, modification of the basic moiety at the end of the side chain, and removal of the charge from the N-terminus. Two of these peptides, 6 and 7 (IC50 values of 0.51 and 0.45 mu M, respectively), show similar potency to the best compounds in the FM 19 series reported thus far. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.045
• 作为产物：
  描述：

  (S)-4-苄基-2-唑烷酮 在 正丁基锂 、 Ti(OiPr)Cl3 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (4R)-5-[(4S)-4-benzyl-2-oxooxazolidin-3-yl]-4-methyl-5-oxopentanenitrile
  参考文献：
  名称：

  Peptide based inhibitors of interleukin-8: structural simplification and enhanced potency

  摘要：

  Important areas of a lead peptide inhibitor of IL-I had been previously identified. Chemical modification led to the identification of key amide bonds which allowed the replacement of the central section of the peptide with modified amino acids and spacers. This approach led to inhibitors of lower molecular weight and of increased potency. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00036-x

文献信息

• Toward the Total Synthesis of the Brasilinolides: Stereocontrolled Assembly of a C1−C19 Polyol Segment
  作者：Ian Paterson、Friedrich A. Mühlthau、Christopher J. Cordier、Michael P. Housden、Paul M. Burton、Olivier Loiseleur

  DOI：10.1021/ol802562b

  日期：2009.1.15

  Two highly convergent syntheses of a fully protected C1−C19 polyol subunit of the brasilinolide family of immunosuppressive macrolides are described, exploiting boron-mediated 1,5-anti aldol couplings to form the C8−C9 and C13−C14 bonds.

  描述了两个高度收敛的合成的免疫抑制性大环内酯的巴西内酯类的完全保护的C1-C19多元醇亚基，利用硼介导的1，5-抗羟醛偶联形成C8-C9和C13-C14键。
• Enantioselective Michael reactions. Diastereoselective reactions of chlorotitanium enolates of chiral N-acyloxazolidinones with representative electrophilic olefins
  作者：David A. Evans、Mark T. Bilodeau、Todd C. Somers、Jon Clardy、David Cherry、Yoko Kato

  DOI：10.1021/jo00020a007

  日期：1991.9

  In the present study we wish to report the details of the diastereoselective reactions of titanium enolates derived from N-propionyloxazolidone 1 in inter-and intramolecular Michael reactions with ethyl vinyl ketone, methyl acrylate, and acrylonitrile (eq 1).