(E)-2-phenyl-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen>-5(4H)-oxazolone | 154663-57-7

• 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
• 英文名称: (E)-2-phenyl-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen>-5(4H)-oxazolone
• 英文别名: (4E)-4-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 154663-57-7
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: RYNZXKIYXZEHJB-SERMCNLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 (E)-2-phenyl-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen>-5(4H)-oxazolone 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以48%的产率得到(5R,6R)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-8,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.5]deca-1,8-dien-4-one
  参考文献：
  名称：

  Diels-Alder reactions of (E)-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone with heterogeneous catalysts

  摘要：

  Diels-Alder reactions of (E)-2-Phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone with 2,3-dimethylbutadiene, cyclopentadiene, and 2-methyl-1,3-butadiene (isoprene) are catalysed by silica gel and aluminium, titanium, and zinc catalyst supported on silica gel. Overall conversion and asymmetric induction are obtained with very low percentages of E/Z isomerisation. The best results are obtained with ZnCl2 supported on silica gel, and by carrying out the reaction without a solvent. The stereochemistry of the major cycloadducts has been determined by single crystal X-ray structure determination and AM1 calculations of the corresponding transition structures. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00295-9
• 作为产物：
  描述：

  马尿酸 、 1,2;5,6-Di-O-isopropylidenmannit 生成 (E)-2-phenyl-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen>-5(4H)-oxazolone
  参考文献：
  名称：

  Cativiela Carlos, Diaz-de-Villegas Maria D., Jimenez Ana I., Lahoz Fernan+, Tetrahedron Lett, 35 (1994) N 4, S 617-620

  摘要：

  DOI：

文献信息

• 1,3-Dipolar cycloaddition of diazomethane to chiral azlactones. Experimental and theoretical studies
  作者：Carlos Cativiela、María D. Díaz-de-Villegas、JoséI. García、Ana I. Jiménez

  DOI：10.1016/s0040-4020(97)00120-8

  日期：1997.3

  The reaction of (E)-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone with diazomethane has been studied under a variety of reaction conditions, and the results compared with those obtained with the corresponding (Z)-isomer. The origin of the high diastereofacial selectivity in the cyclopropane products, observed with both oxazolones, is discussed in the light of theoretical calculations

  （E）-2-苯基-4-[（S）-2,2-二甲基-1,3-二氧戊环-4-基亚甲基] -5（4 H）-恶唑酮与重氮甲烷的反应已在多种条件下进行了研究反应条件，并将结果与​​用相应的（Z）-异构体获得的结果进行比较。根据第一步反应的理论计算，即在半经验（AM1）下进行的重氮甲烷的1,3-偶极环加成，讨论了用两种恶唑酮观察到的环丙烷产物中高非对映选择性的起源。）和从头算起（RHF / 3-21G）级别。两个理论水平正确预测在协同反应途径，导致所述的不对称诱导的方向Δ 1 -吡唑啉。AM1计算还预测了逐步反应路径的存在，该反应会导致开链反应中间体，但从头算结果并不支持。
• 1,3-Dipolar cycloaddition of diazomethane with a chiral azlactone
  作者：Carlos Cativiela、María D Díaz-de-Villegas、Ana I Jiménez、Fernando Lahoz

  DOI：10.1016/s0040-4039(00)75853-9

  日期：1994.1

  The chiral Z-azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde reacted with diazomethane to afford stereoselectively and diastereoselectively a cis spiro-azlactone. Solvent and temperature dependence of the ratio of the products is described