(4R,5S)-4-methyl-5-phenyl-3-phenylacetyl-oxazolidin-2-one | 96930-16-4

• 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: (4R,5S)-4-methyl-5-phenyl-3-phenylacetyl-oxazolidin-2-one
• 英文别名: (4R,5S)-4-methyl-5-phenyl-3-(2-phenylacetyl)-1,3-oxazolidin-2-one
• CAS: 96930-16-4
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: FJKWWFGNYPFCTF-CXAGYDPISA-N

物化性质

• 沸点：
  488.1±44.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  (4R,5S)-4-methyl-5-phenyl-3-phenylacetyl-oxazolidin-2-one 在 Schwartz's reagent 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以51%的产率得到苯乙醛
  参考文献：
  名称：

  Mild and Selective Hydrozirconation of Amides to Aldehydes Using Cp₂Zr(H)Cl:  Scope and Mechanistic Insight

  摘要：

  An investigation of the use of Cp2Zr(H)Cl (Schwartz's reagent) to reduce a variety of amides to the corresponding aldehydes under very mild reaction conditions and in high yields is reported. A range of tertiary amides, including Weinreb's amides, can be converted directly to the corresponding aldehydes with remarkable chemoselectivity. Primary and secondary amides proved to be viable substrates for reduction as well, although the yields were somewhat diminished as compared to the corresponding tertiary amides. Results from NMR experiments suggested the presence of a stable, 18-electron zirconacycle intermediate that presumably affords the aldehyde upon water or silica gel workup. A series of competition experiments revealed a preference of the reagent for substrates in which the lone pair of the nitrogen is electron releasing and thus more delocalized across the amide bond by resonance. This trend accounts for the observed excellent selectivity for tertiary amides versus esters. Experiments regarding the solvent dependence of the reaction suggested a kinetic profile similar to that postulated for the hydrozirconation of alkenes and alkynes. Addition of p-anisidine to the reaction intermediate resulted in the formation of the corresponding imine mimicking the addition of water that forms the aldehyde.

  DOI：

  10.1021/ja066362+
• 作为产物：
  描述：

  苯乙酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 (4R,5S)-4-methyl-5-phenyl-3-phenylacetyl-oxazolidin-2-one
  参考文献：
  名称：

  WO2007/41366

  摘要：

  公开号：

文献信息

• Asymmetric synthesis of optically active 2,3-diarylsuccinic acids by oxidative homocoupling of chiral 3-(arylacetyl)-2-oxazolidones
  作者：Naoki Kise、Kimikage Kumada、Yuichi Terao、Nasuo Ueda

  DOI：10.1016/s0040-4020(98)83006-8

  日期：1998.3

  Oxidative homocoupling of chiral 3-(arylacetyl)-2-oxazolidones 1 was achieved by treatment with DABCO-TiCl4 or DMAP-TiCl4 and afforded the corresponding dimers stereospecifically. The reaction of (4S)- and (4R)-substituted 1 gave (S,S)- and (R,R)-dimers respectively. The obtained dimers were easily transformed to the corresponding 2,3-diaryl succinic acids. This reaction therefore provides a useful

  通过用DABCO-TiCl 4或DMAP-TiCl 4处理，实现手性3-（芳基乙酰基）-2-恶唑烷酮1的氧化均偶联，并立体定向提供相应的二聚体。（4S）-和（4R）-取代的1的反应得到（S，S）-和（R，R）-二聚体。获得的二聚体容易转化为相应的2，3-二芳基琥珀酸。因此，该反应提供了用于合成光学纯的2，3-二芳基琥珀酸的有用方法。芳基上的给电子基团的对位取代不会抑制氧化偶合。然而，对位取代的吸电子基团和邻位取代基阻碍了偶联。
• Enantioselective synthesis of 2-substituted 3-aminopropanoic acid (β-alanine) derivatives which are β-analogues of aromatic amino acids
  作者：Elena Arvanitis、Holger Ernst、Alice A. LudwigéD’Souza、Andrew J. Robinson、Peter B. Wyatt

  DOI：10.1039/a706163c

  日期：——

  3-Aminopropanoic acid derivatives with a phenyl, 4-hydroxyphenyl, benzyl or indol-3-yl substituent at C-2 can be prepared enantioselectively by routes involving electrophilic attack of synthetic equivalents of [H2NCH2]+ upon enolates derived from chiral 3-acyl-1,3-oxazolidin-2-ones. tert-Butyl bromoacetate may be used as the electrophile, with subsequent introduction of nitrogen through the Curtius reaction, using the sequence of reagents (i) CF3CO2H; (ii) (PhO)2P(O)N3, Et3N, PhCH2OH; alternatively, direct electrophilic reaction with 1-[N-(benzyloxycarbonyl)aminomethyl]benzotriazole 4c or benzyl N-(acetoxymethyl)carbamate 2d introduces a protected aminomethyl group in a single step.

  具有苯基、4-羟基苯基、苄基或吲哚-3-基的C-2取代基的3-氨基丙酸衍生物可以通过涉及合成[H2NCH2]+的亲电攻击的路线，从手性3-酰基-1,3-恶唑烷-2-酮衍生的烯醇盐选择性地制备。可以使用叔丁基溴乙酸酯作为亲电试剂，随后通过Curtius反应引入氮，使用试剂序列（i）CF3CO2H；（ii）(PhO)2P(O)N3，Et3N，PhCH2OH；或者，直接与1-[N-(苄氧羰基)氨基甲基]苯并三唑4c或苄基N-(乙酸甲酯)氨基甲酸酯2d进行亲电反应，一步引入保护的氨基甲基基团。
• Asymmetric synthesis of α-fluoro ketones using α-fluoro oxazolidinone carboximides
  作者：Franklin A. Davis、Parimala V.N. Kasu

  DOI：10.1016/s0040-4039(98)01296-9

  日期：1998.8

  Addition of Grignard reagents to enantiopure α-fluoro N-methoxy-N-methylamides 5 affords α-fluoro ketones (R)-6 in >96% ee.

  向对映体纯的α-氟代N-甲氧基-N-甲基酰胺5中添加格氏试剂可得到> 96％ee的α-氟代酮（R）-6。
• Organic Compounds
  申请人：Bebernitz Gregory Raymond

  公开号：US20080312256A1

  公开（公告）日：2008-12-18

  The present invention provides compounds of the formula which are activators of glucokinase activity and, thus, may be employed as therapeutic agents for the treatment of glucokinase mediated conditions. Accordingly, the compounds of formula (I) may be employed for the prevention and the treatment of impaired glucose tolerance, type 2 diabetes and obesity.

  本发明提供了以下式子的化合物，它们是葡萄糖激酶活性的激活剂，因此可以作为治疗葡萄糖激酶介导疾病的治疗剂。因此，式（I）的化合物可用于预防和治疗糖耐量受损、2型糖尿病和肥胖症。
• Thiazolo[5,4-B]pyridine glucokinase activators
  申请人：Novartis AG

  公开号：US08252931B2

  公开（公告）日：2012-08-28

  The present invention provides compounds of the formula which are activators of glucokinase activity and, thus, may be employed as therapeutic agents for the treatment of glucokinase mediated conditions. Accordingly, the compounds of formula (I) may be employed for the prevention and the treatment of impaired glucose tolerance, type 2 diabetes and obesity.

  本发明提供了式子（I）的化合物，它们是葡萄糖激酶活性的激活剂，因此可以作为治疗葡萄糖激酶介导疾病的治疗剂。因此，式（I）的化合物可用于预防和治疗糖耐量受损、2型糖尿病和肥胖症。