(2R,4S)-3-苯甲酰基-2-(叔丁基)-4-甲基-1,3-恶唑烷-5-酮 | 104057-65-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2R,4S)-3-苯甲酰基-2-(叔丁基)-4-甲基-1,3-恶唑烷-5-酮
• 英文名称: (2R,4S)-3-benzoyl-2-(tert-butyl)-4-methyl-1,3-oxazolidin-5-one
• 英文别名: (2R,4S)-3-Benzoyl-2-tert-butyl-4-methyl-1,3-oxazolidin-5-one；(2R,4S)-3-Benzoyl-2-(tert-butyl)-4-methyloxazolidin-5-on；(4S)-3-benzoyl-2-t-butyl-4-methyl-1,3-oxazolidin-5-one
• CAS: 104057-65-0
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: VQCFYKBTJKIGNX-IINYFYTJSA-N

物化性质

• 沸点：
  426.9±38.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (2R,4S)-3-苯甲酰基-2-(叔丁基)-4-甲基-1,3-恶唑烷-5-酮 在 sodium methylate 、 cesium fluoride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 为溶剂， 反应 24.58h， 生成
  参考文献：
  名称：

  Fluorination of aromatic compounds from 1-aryl-3,3-dimethyltriazenes and fluoride anions in acidic medium

  摘要：

  We propose here a new methodology to prepare 3-fluoro-alpha -methylphenylalanine in which fluorine is introduced at the end of the synthesis, on an elaborated substrate bearing a triazeno substituent which is decomposed by triflic acid in the presence of fluoride anions (yield = 31% versus F-19(-)). As F-18(-) cannot be available free of other basic anions, this technique has been modified and adapted with some success to the radiosynthesis of [F-18]-3-fluoro-alpha -methylphenylalanine. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(00)00377-8
• 作为产物：
  描述：

  rac-3-Benzoyl-2-(t-butyl)-1,3-oxazolidin-5-on 在 lithium diisopropyl amide 作用下， 反应 14.33h， 生成 (2R,4S)-3-苯甲酰基-2-(叔丁基)-4-甲基-1,3-恶唑烷-5-酮
  参考文献：
  名称：

  制备柱chromatographische Enantiomerentrennung冯synthetischnützlichencyclischen Acetalen †

  摘要：

  综合有用的环缩醛的制备型色谱分离度

  DOI：

  10.1002/hlca.19880710541

文献信息

• Asymmetric autocatalysis induced by meteoritic amino acids with hydrogen isotope chirality
  作者：Tsuneomi Kawasaki、Masako Shimizu、Daisuke Nishiyama、Masateru Ito、Hitomi Ozawa、Kenso Soai

  DOI：10.1039/b908754k

  日期：——

  Achiral meteoritic amino acids, glycine and α-methylalanine, with hydrogen isotope (D/H) chirality, acted as the source of chirality in asymmetric autocatalysis with amplification of ee to afford highly enantioenriched 5-pyrimidyl alkanols.

  非手性的陨石氨基酸甘氨酸和α-甲基丙氨酸，具有氢同位素（D/H）手性，在不对称自催化中作为手性的来源，通过放大ee，得到高度富集的5-嘧啶基烷醇。
• N,O-Acetals from Pivalaldehyde and Amino Acids for the ?-Alkylation with Self-Reproduction of the Center of Chirality. Enolates of 3-Benzoyl-2-(tert-butyl)-1,3-oxazolidin-5-ones
  作者：Dieter Seebach、Antoine Fadel

  DOI：10.1002/hlca.19850680521

  日期：1985.8.14

  The sodium salts of (S)-alanine, (S)-phenylalanine, (S)-valine, and (S)-methionine are condensed with pivalaldehyde to imines 5. Cyclization by treatment with benzoyl chloride in cold CH2Cl2 gives mainly (4:1 to > 99:1) the (2S,4S)-4-alkyl-3-benzoyl-2-(tert-butyl)-1,3-oxazolidin-5-ones (6; cis-configuration) in high yields (85–95%). The oxazolidinones 6 and 7 are deprotonated with lithium diethylamide

  （S）-丙氨酸，（S）-苯丙氨酸，（S）-缬氨酸和（S）-蛋氨酸的钠盐与新戊醛缩合成亚胺5。通过在冷的CH 2 Cl 2中用苯甲酰氯处理进行环化，主要得到（4：1至> 99：1）（2 S，4 S）-4-烷基-3-苯甲酰基-2-（叔丁基）-1 ，3-恶唑烷-5-酮（6；顺式构型）高产（85–95％）。恶唑烷酮6和7用二乙氨基锂（LDEA）在四氢呋喃（THF）中进行质子化，烷基化（Mel，苄基溴）或羟烷基化（苯甲醛）分别以高非对映选择性（9：1至50：1 ）分别形成4,4-二取代的恶唑烷酮9和10。 ；相对话题性ul）。三种恶唑烷酮水解为已知构型和光学纯度的氨基酸表明，在该过程中很少发生外消旋作用。
• Herstellung enantiomerenreiner, ?-alkylierter Lysin-, Ornithin- und Tryptophan-Derivate
  作者：Marlyse Gander-Coquoz、Dieter Seebach

  DOI：10.1002/hlca.19880710124

  日期：1988.2.3

  Synthesis of Enantiomerically Pure, α-Alkylated Lysine, Ornithine, and Tryptophan Derivatives

  对映体纯的α-烷基赖氨酸，鸟氨酸和色氨酸衍生物的合成
• Synthése enantiosélective d'-α-aryl amino acides: substitution nucléophile aromatique sur le fluorobenzéne chrome tricarbonyle d'énolates chiraux
  作者：M. Chaari、A. Jenhi、J.-P. Lavergne、Ph. Viallefont

  DOI：10.1016/0022-328x(91)86213-a

  日期：1991.1

  We report here a convenient synthesis of optically pure alpha-aryl amino acids by enantioselective substitution of fluorobenzene tricarbonylchromium using the Schiff bases of L-alanine methyl ester with (1R,2R,5R)-2hydroxy-3-pinanone in presence of LDA or deprotonated 2-(tert-butyl)-4-methyl-1,3-oxazolidin-5 one.
• Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 2. Retarded Metabolism of Lipopeptides by Insertion of .alpha.-Substituted .alpha.-Amino Acids
  作者：Alexandra Frauer、Michaela Mehlfuehrer、Klaus Thirring、Heinz Berner

  DOI：10.1021/jo00094a038

  日期：1994.7

  The synthesis of the lipopeptide 1, which exhibits both immunological activity (induction of the colony stimulating factor (CSF)) and stability against metabolic degradation, has been described. A detailed investigation of the course of the ene reaction between the dipeptide 21 and butyl glyoxylate enabled us to use this type of pericyclic reaction for the establishment of the essential pentenoic acid side chain in 23. The required amino acid 15 was obtained by enzymatic hydrolysis of the corresponding rac-ester 19. The absolute configuration of 1 was assigned by oxidative cleavage of the double bond in 24 and 25 followed by comparison of the degradation products with authentic samples.