(4S)-3-[(2S,3S)-2-bromo-3-phenylbutanoyl]-4-phenyl-1,3-oxazolidin-2-one | 148706-31-4

• 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: (4S)-3-[(2S,3S)-2-bromo-3-phenylbutanoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 148706-31-4
• 化学式: C₁₉H₁₈BrNO₃
• 分子量: 388.261
• InChiKey: SKCCGTVXHVZQHZ-XKQJLSEDSA-N

物化性质

• 沸点：
  514.2±50.0 °C(predicted)
• 密度：
  1.433±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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-[(2S,3S)-2-bromo-3-phenylbutanoyl]-4-phenyl-1,3-oxazolidin-2-one 在 tetramethylguanidinum azide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 (4S)-3-[(2R,3S)-2-azido-3-phenylbutanoyl]-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  β-甲基苯丙氨酸四种异构体合成的新策略

  摘要：

  摘要报道了烯丙基应变效应在硼烯醇化物和不对称迈克尔样加成/亲电溴化反应中的应用，用于不对称合成个别受限氨基酸的异构体。对于β-取代的α-氨基酸，所有最终的光学纯产品都与真实样品相同，这为确认本报告中新方法的立体化学控制的分配提供了进一步明确的证据。

  DOI：

  10.1080/00397919508010789
• 作为产物：
  描述：

  (+/-)-3-苯基丁酸 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟甲磺酸二丁硼 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (4S)-3-[(2S,3S)-2-bromo-3-phenylbutanoyl]-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Li, Guigen; Patel, Dinesh; Hruby, Victor J., Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3057 - 3060

  摘要：

  DOI：

文献信息

• Diastereospecific tandem Michael-like addition / electrophilic bromination: A one-pot tandem asymmetric synthesis of precursors of unusual amino acids
  作者：Guigen Li、Mark A. Jarosinski、Victor J. Hruby

  DOI：10.1016/s0040-4039(00)77625-8

  日期：1993.4

  A systematic series of key intermediates of unusual β-methyl-amino acids have been synthesized by using a modified Evans auxiliary in an asymmetric Michael-like reaction followed by direct bromination in a one-pot reaction.

  通过在不对称迈克尔样反应中使用修饰的Evans辅助剂，然后在单锅反应中直接溴化，合成了系统化的一系列非常规β-甲基氨基酸关键中间体。
• Macrocyclic Ghrelin Receptor Antagonists and Inverse Agonists and Methods of Using the Same
  申请人：Hoveyda Hamid R.

  公开号：US20110105389A1

  公开（公告）日：2011-05-05

  The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (GRLN, growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and/or variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as antagonists or inverse agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, obesity and obesity-associated disorders, appetite or eating disorders, addictive disorders, cardiovascular disorders, gastrointestinal disorders, genetic disorders, hyperproliferative disorders, central nervous system disorders and inflammatory disorders.

  本发明提供了新型构象定义的大环化合物，已被证明是生长激素分泌素受体（GRLN，生长激素分泌素受体，GHS-R1a及其亚型、异构体和/或变种）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的拮抗剂或逆向激动剂，以及用于治疗和预防一系列医学疾病，包括但不限于代谢和/或内分泌紊乱、肥胖和与肥胖相关的疾病、食欲或进食紊乱、成瘾紊乱、心血管疾病、胃肠道疾病、遗传疾病、过度增殖性疾病、中枢神经系统疾病和炎症性疾病。
• [EN] MACROCYCLIC GHRELIN RECEPTOR ANTAGONISTS AND INVERSE AGONISTS AND METHODS OF USING THE SAME<br/>[FR] ANTAGONISTES ET AGONISTES INVERSES MACROCYCLIQUES DU RÉCEPTEUR DE LA GHRÉLINE ET LEURS MÉTHODES D'UTILISATION
  申请人：TRANZYME PHARMA INC

  公开号：WO2011053821A1

  公开（公告）日：2011-05-05

  The present invention provides novel conformationalIy- defined macrocyclic compounds of formula (I) that have been demonstrated to be selective modulators of the ghrelin receptor (GRLN, growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and/or variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as antagonists or inverse agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, obesity and obesity- associated disorders, appetite or eating disorders, addictive disorders, cardiovascular disorders, gastrointestinal disorders, genetic disorders, hyperproliferative disorders, central nervous system disorders and inflammatory disorders.
• Li, Guigen; Patel, Dinesh; Hruby, Victor J., Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3057 - 3060
  作者：Li, Guigen、Patel, Dinesh、Hruby, Victor J.

  DOI：——

  日期：——
• A New Strategy for the Synthesis of Four Individual Isomers of β-Methylphenylalanine
  作者：Feng-Di Lung、Guigen Li、Bith-Show Lou、Victor J. Hruby

  DOI：10.1080/00397919508010789

  日期：1995.1

  Abstract The application of an allylic strain effect in boron enolates and asymmetric Michael-like addition/electrophilic bromination reactions is reported for the asymmetric synthesis of the individual isomers of unusual constrained amino acids. For β-substituted α-amino acids, all of the final optically pure products were identical to authentic samples, which provided further and unequivocal evidence

  摘要报道了烯丙基应变效应在硼烯醇化物和不对称迈克尔样加成/亲电溴化反应中的应用，用于不对称合成个别受限氨基酸的异构体。对于β-取代的α-氨基酸，所有最终的光学纯产品都与真实样品相同，这为确认本报告中新方法的立体化学控制的分配提供了进一步明确的证据。