(4S)-4-phenyl-3-(3-phenylbutanoyl)oxazolidin-2-one | 146137-33-9

• 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)-4-phenyl-3-(3-phenylbutanoyl)oxazolidin-2-one
• 英文别名: (3(3R),4S)-4-phenyl-3-(3-phenylbutanoyl)-2-oxazolidinone；(4S)-4-phenyl-3-[(3R)-3-phenylbutanoyl]-1,3-oxazolidin-2-one
• CAS: 146137-33-9
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: QTEDIMBXZHKQES-RHSMWYFYSA-N

物化性质

• 沸点：
  496.5±44.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 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)-4-phenyl-3-(3-phenylbutanoyl)oxazolidin-2-one 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 、 tetramethylguanidinum azide 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 (4S)-3-[(2R,3S)-2-azido-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：
• 作为产物：
  描述：

  (+/-)-3-苯基丁酸 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (4S)-4-phenyl-3-(3-phenylbutanoyl)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。
• Diastereoselective copper-catalysed 1,4-addition of Grignard reagents to N-enoyl oxazolidinones
  作者：Michal Drusan、Zuzana Galeštoková、Radovan Šebesta

  DOI：10.1039/c3ra42024h

  日期：——

  Conjugate additions of organometallic reagents to α,β-unsaturated carboxylic acid derivatives give access to numerous β-substituted chiral building blocks. Chiral oxazolidinones serve as useful surrogates of carboxylic function in the asymmetric conjugate addition of Grignard reagents. N-Enoyl oxazolidinones undergo this 1,4-addition with a catalytic amount of copper salt and using either chiral or

  将有机金属试剂共轭添加到α，β-不饱和羧酸衍生物中可以得到许多β-取代的手性结构单元。手性恶唑烷酮在格氏试剂的不对称共轭加成中可用作有用的羧基官能替代物。N-烯丙基恶唑烷酮与1,4-催化量的铜盐进行加成反应，并使用手性或非手性膦配体。特别地，手性二茂铁基膦烷恶唑啉被证明可用于实现高非对映选择性。以高收率和高非对映选择性（直至单一非对映异构体）获得所得的N-酰基恶唑烷酮。
• Palladium-Catalyzed Diastereoselective Synthesis of 3-Arylbutanoic Acid Derivatives
  作者：Wubin Zhi、Jingya Li、Dapeng Zou、Yusheng Wu、Yangjie Wu

  DOI：10.1021/acs.joc.7b02104

  日期：2017.12.1

  first palladium-catalyzed diastereoselective conjugate addition of arylboronic acids to chiral imides is reported. The catalytic system employing 4-tert-butyloxazolidin-2-one as the chiral auxiliary in a mixed solvent system of MeOH/H2O (1:3) under an air atmosphere provides the optically active 3-arylbutanoic acid derivatives in excellent yields with high diastereoselectivity.

  据报道，芳基硼酸第一次钯催化的非对映选择性共轭加成到手性酰亚胺上。在空气气氛下，在MeOH / H 2 O（1：3）混合溶剂体系中，以4-叔丁基恶唑烷-2-酮为手性助剂的催化体系提供了具有优异收率的旋光性3-芳基丁酸衍生物。高非对映选择性。
• Diastereoselection in the conjugate additions of organocopper reagents to N-enoyloxazolidinones
  作者：David R Williams、William S Kissel、Jie Jack Li

  DOI：10.1016/s0040-4039(98)01966-2

  日期：1998.11

  A survey of conjugate additions of Yamamoto organocopper reagents to N-enoyl-4-substituted oxazolidinones is reported. Diastereofacial selectivity is reversed for 4-phenyl and 4-benzyloxazolidinones of the same relative configuration. Alkenylcopper reagents demonstrate superior results in asymmetric additions using the 4-phenyloxazolidinone auxiliary.

  据报道，对N-烯基-4-取代的恶唑烷酮类化合物中山本有机铜试剂的共轭加成进行了调查。具有相同相对构型的4-苯基和4-苄基恶唑烷酮的非对映选择性相反。链烯铜试剂在使用4-苯基恶唑烷酮辅助剂的不对称添加中显示出优异的结果。
• 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。