3,5-Dinitrophenyloxirane | 1246058-64-9

• 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: 3,5-Dinitrophenyloxirane
• 英文别名: 2-(3,5-dinitrophenyl)oxirane
• CAS: 1246058-64-9
• 化学式: C₈H₆N₂O₅
• 分子量: 210.146
• InChiKey: ZAPKEWCAJBHZRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯磺酸 、 3,5-Dinitrophenyloxirane 以 1,4-二氧六环 、 二乙二醇二甲醚 为溶剂， 生成 2-(3,5-dinitrophenyl)-2-hydroxyethyl 4-methoxybenzenesulfonate
  参考文献：
  名称：

  Nonadditive effects of structural factors in reactions of aryloxiranes with arenesulfonic acids. Observation of isoparametricity phenomenon

  摘要：

  In reactions of aryloxiranes XC6H4(3)CH(O)CH2 with arenesulfonic acids YC6H4SO3H in a mixture of dioxane with diglyme (1: 1) at 265 K the nonadditive effects of substituents X and Y were strongly revealed, therefore it was possible to observe experimentally the isoparametricity phenomenon: In the isoparametric point sigma(X) (IP) = 1.42 with respect to the X substituent constant the rate of the oxirane ring opening did not depend on the structure of Y (rho(Y) (X) = 0).

  DOI：

  10.1134/s107042801105006x
• 作为产物：
  描述：

  1,3-二硝基-5-乙烯基-苯 在 chiral iron "twin coronet" porphyrin 亚碘酰苯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3,5-Dinitrophenyloxirane 、 (S)-2-(3,5-Dinitro-phenyl)-oxirane
  参考文献：
  名称：

  手性联四氢萘带“双冠”卟啉的合成。苯乙烯衍生物的催化和不对称环氧化

  摘要：

  在卟啉的两个面上带有光学活性 1,1'-双四氢萘衍生物的“双冠”卟啉被制备为模拟细胞色素 P-450 的对映选择性氧化催化剂。相应的铁 (III) 卟啉的失色异构体在高 ee (61–89%) 和高产物选择性下催化被吸电子基团取代的苯乙烯的环氧化。

  DOI：

  10.1246/cl.1991.1933

文献信息

• Structure-Activity Relationship in a Series of Adrenergic β-Blocking Agents Related to 1-(4-Nitrophenyl)-1-hydroxy-2-isopropylaminoethane (INPEA)¹
  作者：P. Somani、Romeo T. Bachand、W. Murmann、L. Almirante

  DOI：10.1021/jm00324a006

  日期：1966.11
• Synthesis of Chiral Bitetralin-strapped “Twin Coronet” Porphyrins. Catalytic and Asymmetric Epoxidation of Styrene Derivatives
  作者：Yoshinori Naruta、Nobuo Ishihara、Fumito Tani、Kazuhiro Maruyama

  DOI：10.1246/cl.1991.1933

  日期：1991.11

  “Twin-coronet” porphyrins bearing optically active 1,1′-bitetrahydronaphthalene derivatives on the both faces of the porphyrin were prepared as enantioselective oxidation catalysts modeling on cytochrome P-450s. The eclipsed isomer of the corresponding iron(III) porphyrins catalyzed epoxidation of styrenes substituted with electron-withdrawing groups in high e.e. (61–89%) and high product selectivity

  在卟啉的两个面上带有光学活性 1,1'-双四氢萘衍生物的“双冠”卟啉被制备为模拟细胞色素 P-450 的对映选择性氧化催化剂。相应的铁 (III) 卟啉的失色异构体在高 ee (61–89%) 和高产物选择性下催化被吸电子基团取代的苯乙烯的环氧化。
• Nonadditive effects of structural factors in reactions of aryloxiranes with arenesulfonic acids. Observation of isoparametricity phenomenon
  作者：I. V. Shpan’ko、I. V. Sadovaya、N. V. Kulikova

  DOI：10.1134/s107042801105006x

  日期：2011.5

  In reactions of aryloxiranes XC6H4(3)CH(O)CH2 with arenesulfonic acids YC6H4SO3H in a mixture of dioxane with diglyme (1: 1) at 265 K the nonadditive effects of substituents X and Y were strongly revealed, therefore it was possible to observe experimentally the isoparametricity phenomenon: In the isoparametric point sigma(X) (IP) = 1.42 with respect to the X substituent constant the rate of the oxirane ring opening did not depend on the structure of Y (rho(Y) (X) = 0).