(R)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one | 136159-65-4

• 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: (R)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one
• 英文别名: (R)-4-benzyl-3-(3-phenyl-propionyl)-oxazolidin-2-one；(4R)-4-benzyl-3-(3-phenylpropanoyl)-1,3-oxazolidin-2-one
• CAS: 136159-65-4
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: CDSPCWKYSYEPMH-QGZVFWFLSA-N

物化性质

• 熔点：
  103-105 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  502.5±29.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 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：

  (R)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 19.83h， 生成 N-Boc-D-苯丙氨醇
  参考文献：
  名称：

  （的简明对映选择性合成- [R）-selegiline，（小号）-benzphetamine和正式合成（- [R ）手性通过酰亚胺烯醇化物的电叠氮化-sitagliptin

  摘要：

  简明和（的高产对映选择性合成- [R）-selegiline，抗帕金森氏药，（小号）-benzphetamine，抗肥胖剂，以及（小号）-sitagliptin，抗糖尿病药物已经描述从市售起始可用的原料采用Evans手性酰亚胺烯酸酯的亲电子叠氮化作为关键的手性诱导步骤，该步骤以非对映选择性高的方式进行（> 99％）。

  DOI：

  10.1016/j.tetasy.2014.11.014
• 作为产物：
  描述：

  3-苯基丙酸 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.75h， 生成 (R)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one
  参考文献：
  名称：

  (E)-Alkene and Ethylene Isosteres Substantially Alter the Hydrogen-Bonding Network in Class II MHC A^q/Glycopeptide Complexes and Affect T-Cell Recognition

  摘要：

  The structural basis for antigen presentation by class II major histocompatibility complex (MHC) proteins to CD4(+) T-cells is important for understanding and possibly treating autoimmune diseases. In the work described in this paper, (E)-alkene and ethylene amide-bond isosteres were used to investigate the effect of removing hydrogen-bonding possibilities from the CII259-270 glycopeptide, which is bound by the arthritis-associated murine A(q) class II MHC protein. The isostere-modified glycopeptides showed varying and unexpectedly large losses of A(q) binding that could be linked to the dynamics of the system. Molecular dynamics (MD) simulations revealed that the backbone of CII259-270 and the A(q) protein are able to form up to 11 hydrogen bonds, but fewer than this number are present at any one time. Most of the strong hydrogen-bond interactions were formed by the N-terminal part of the glycopeptide, i.e., in the region where the isosteric replacements were made. The structural dynamics also revealed that hydrogen bonds were strongly coupled to each other; the loss of one hydrogen-bond interaction had a profound effect on the entire hydrogen-bonding network. The A(q) binding data revealed that an ethylene isostere glycopeptide unexpectedly bound more strongly to A(q) than the corresponding (E)-alkene, which is in contrast to the trend observed for the other isosteres. Analysis of the MD trajectories revealed that the complex conformation of this ethylene isostere was structurally different and had an altered molecular interaction pattern compared to the other A(q)/glycopeptide complexes. The introduced amide-bond isosteres also affected the interactions of the glycopeptide/A(q) complexes with T-cell receptors. The dynamic variation of the patterns and strengths of the hydrogen-bond interactions in the class II MHC system is of critical importance for the class II MHC/peptide/TCR signaling system.

  DOI：

  10.1021/ja2038722

文献信息

• Dess–Martin periodinane oxidative rearrangement for preparation of α-keto thioesters
  作者：Randy Sanichar、Ciaran Carroll、Ryan Kimmis、Bela Reiz、John C. Vederas

  DOI：10.1039/c7ob02959d

  日期：——

  Dess–Martin Periodinane (DMP) mediated oxidative rearrangement reaction was uncovered. The reaction proceeds via oxidation of a β-hydroxy thioester to a β-keto thioester, followed by an α-hydroxylation and then further oxidation to form a vicinal thioester tricarbonyl. This product then rearranges, extruding CO2, to form an α-keto product. The mechanism of the rearrangement was elucidated using 13C labelling

  发现了由Dess-Martin高碘烷（DMP）介导的氧化重排反应。该反应通过将β-羟基硫代酯氧化为β-酮硫代酯，然后进行α-羟基化，然后进一步氧化以形成邻位硫代酯三羰基来进行。然后该产物重排，挤出CO 2，形成α-酮产物。使用13 C标记和中间体以及反应产物的分析阐明了重排的机理。这种有效的方法使得易于制备α-酮硫酯，α-酮硫酯是药学上重要的杂环支架例如喹喔啉酮的合成中的潜在中间体。
• Benzoic acid substituted benzopyrans for the treatment of atherosclerosis
  申请人：Pfizer Products Inc.

  公开号：EP1270000A2

  公开（公告）日：2003-01-02

  A method of treating atherosclerosis in a mammal, including a human, comprising administering to said mammal an amount of the compound of the formula an enantiomer, or the pharmaceutically acceptable salt thereof; effective to treat atherosclerosis, wherein R1, R2 and R3 are as defined herein.

  治疗哺乳动物，包括人类动脉粥样硬化的方法，包括向所述哺乳动物施用公式化合物的量 一个对映体，或其药用可接受的盐； 有效治疗动脉粥样硬化，其中R1、R2和R3如本文所定义。
• [EN] 5-AMINO-4-CARBAMOYL-PYRAZOLE COMPOUNDS AS SELECTIVE AND IRREVERSIBLE T790M OVER WT-EGFR KINASE INHIBITORS AND USE THEREOF<br/>[FR] COMPOSÉS 5-AMINO-4-CARBAMOYL-PYRAZOLE UTILISÉS COMME INHIBITEURS SÉLECTIFS ET IRRÉVERSIBLES DE T790M SUR LA KINASE WT-EGFR, ET LEUR UTILISATION
  申请人：BEIGENE LTD

  公开号：WO2016008411A1

  公开（公告）日：2016-01-21

  Disclosed are compounds of Formula (I), pharmaceutical compositions comprising the same, processes for the preparation thereof, and the use thereof.

  公开了公式(I)的化合物，包括含有该化合物的药物组合物，制备该化合物的方法以及该化合物的用途。
• Fluorinated β²- and β³-Amino Acids: Synthesis and Inhibition of α-Chymotrypsin
  作者：Andrew Abell、Victoria Peddie、Markus Pietsch、Karen Bromfield、Robert Pike、Peter Duggan

  DOI：10.1055/s-0029-1218743

  日期：2010.6

  synthesis of a series of α-fluorinated β²- and β³-amino acid derivatives is described. Stereoselective fluorination at the α-carbon of the β³-amino acids was achieved by deprotonation with lithium diisopropylamide followed by treatment with N-fluorobenzenesulfonimide. Fluorination of β²-amino acids employed the chiral auxiliary (4R)-4-benzyl-2-oxazolidinone. The α-fluorinated amino acids and their non-fluorinated

  描述了一系列α-氟化的β2-和β3-氨基酸衍生物的合成。在的α碳的立体选择性氟化的β ³ α-氨基酸是由去质子化与二异丙基氨基锂，接着用治疗取得Ñ -fluorobenzenesulfonimide。的β氟化² α-氨基酸中使用的手性辅助剂（4 - [R）-4-苄基-2-恶唑烷酮。发现α-氟代氨基酸及其非氟代前体竞争性地抑制α-胰凝乳蛋白酶。 β-氨基酸-氟化-晶体结构-α-胰凝乳蛋白酶-抑制剂
• Processes for preparing substituted chromanol derivatives
  申请人：Pfizer Inc.

  公开号：US06096906A1

  公开（公告）日：2000-08-01

  The invention relates to processes for preparing a compound of the formula (X) and the enantiomer of said compound, wherein the benzoic acid moiety is attached at position 6 or 7 of the chroman ring, and R.sup.1, R.sup.2 and R.sup.3 are as defined herein. The invention further relates to intermediates that are useful in the preparation of the compound of formula (X). ##STR1##

  这项发明涉及制备式（X）化合物及该化合物的对映体的过程，其中苯甲酸基团附加在色苷环的6位或7位，并且R.sup.1、R.sup.2和R.sup.3如本文所定义。该发明还涉及在制备式（X）化合物过程中有用的中间体。