methyl (4R,5S)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate | 151671-04-4

• 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: methyl (4R,5S)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate
• 英文别名: methyl (4R,5S)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate
• CAS: 151671-04-4
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: CTMDTDZMFUABGC-CABCVRRESA-N

物化性质

• 沸点：
  424.3±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (4R,5S)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以11.0 mg的产率得到N-苯甲酰基-(2R,3S)-3-苯基异丝氨酸甲酯
  参考文献：
  名称：

  Dynamic Ligand Exchange of the Lanthanide Complex Leading to Structural and Functional Transformation:  One-Pot Sequential Catalytic Asymmetric Epoxidation-Regioselective Epoxide-Opening Process

  摘要：

  The characteristic property of the lanthanide complex, which easily undergoes a dynamic ligand exchange and alters its structure and function in situ, is described. After the completion of the catalytic asymmetric epoxidation of various a,beta-unsaturated amides 2 in the presence of the Sm-(S)-BINOL-Ph3As=O (1:1:1) complex 1 (2-10 mol %), the addition of Me3SiN3 directly to the reaction mixture led to smooth epoxide-opening at room temperature, affording the corresponding anti-beta-azido-alpha-hydroxyamide 4 in excellent overall yield (up to 99%) with complete regioselectivity and excellent enantiomeric excess (up to >99%). The key to the success of the sequential process was the in situ generation of the highly reactive samarium azide complex through dynamic ligand exchange. In situ IR spectroscopy and other experiments provided strong evidence that the samariurn azide complex was generated. In addition, the relatively high Lewis basicity of the amide moiety had a key role in the high reactivity of both the epoxidation and the epoxide-opening reactions. Examinations of other nucleophiles such as sulfur or carbon nucleophiles as well as transformations of epoxide-opened products are also described.

  DOI：

  10.1021/ja043770+
• 作为产物：
  描述：

  (2R,3R)-(-)-2-hydroxy-3-(benzoylamino)-3-phenylpropanoic acid methyl ester 在 (氯亚甲基)二甲基氯化铵 作用下， 以 吡啶 为溶剂， 反应 1.5h， 以99%的产率得到methyl (4R,5S)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate
  参考文献：
  名称：

  使用维斯迈尔试剂合成恶唑啉

  摘要：

  DOI：

  10.1021/jo000664r

文献信息

• Electrophilic Azido Selenenylation of Alkenes. A Simple Synthetic Route to Racemic Taxol Side Chain
  作者：Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Luana Bagnoli、Francesca Marini、Claudio Santi

  DOI：10.1080/00397919808007031

  日期：1998.6

  Simple alkenes react with PhSeOTf and NaN3 in MeCN to afford beta-phenylseleno azides as the result of a stereospecific trans addition. The regioselectivity of the process is determined by the structure of the alkene.
• Bunnage, Mark E.; Davies, Stephen G.; Goodwin, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1994, # 17, p. 2385 - 2392
  作者：Bunnage, Mark E.、Davies, Stephen G.、Goodwin, Christopher J.

  DOI：——

  日期：——
• Bunnage, Mark E.; Davies, Stephen G.; Goodwin, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1993, # 13, p. 1375 - 1376
  作者：Bunnage, Mark E.、Davies, Stephen G.、Goodwin, Christopher J.

  DOI：——

  日期：——
• Dynamic Ligand Exchange of the Lanthanide Complex Leading to Structural and Functional Transformation:  One-Pot Sequential Catalytic Asymmetric Epoxidation-Regioselective Epoxide-Opening Process
  作者：Shin-ya Tosaki、Riichiro Tsuji、Takashi Ohshima、Masakatsu Shibasaki

  DOI：10.1021/ja043770+

  日期：2005.2.1

  The characteristic property of the lanthanide complex, which easily undergoes a dynamic ligand exchange and alters its structure and function in situ, is described. After the completion of the catalytic asymmetric epoxidation of various a,beta-unsaturated amides 2 in the presence of the Sm-(S)-BINOL-Ph3As=O (1:1:1) complex 1 (2-10 mol %), the addition of Me3SiN3 directly to the reaction mixture led to smooth epoxide-opening at room temperature, affording the corresponding anti-beta-azido-alpha-hydroxyamide 4 in excellent overall yield (up to 99%) with complete regioselectivity and excellent enantiomeric excess (up to >99%). The key to the success of the sequential process was the in situ generation of the highly reactive samarium azide complex through dynamic ligand exchange. In situ IR spectroscopy and other experiments provided strong evidence that the samariurn azide complex was generated. In addition, the relatively high Lewis basicity of the amide moiety had a key role in the high reactivity of both the epoxidation and the epoxide-opening reactions. Examinations of other nucleophiles such as sulfur or carbon nucleophiles as well as transformations of epoxide-opened products are also described.
• The Synthesis of Oxazolines Using the Vilsmeier Reagent
  作者：Peter G. M. Wuts、Jill M. Northuis、Tricia A. Kwan

  DOI：10.1021/jo000664r

  日期：2000.12.1