1-ethoxyvinyl 4-nitrobenzoate | 188488-79-1

• 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: 1-ethoxyvinyl 4-nitrobenzoate
• 英文别名: 1-Ethoxyethenyl 4-nitrobenzoate
• CAS: 188488-79-1
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: CGOVGPWXLIMJPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(+)-ethyl-α-(para-tolylsulfinyl) acetate 、 1-ethoxyvinyl 4-nitrobenzoate 以 甲苯 为溶剂， 生成 、
  参考文献：
  名称：

  Highly asymmetric Pummerer-type reaction induced by ethoxy vinyl esters

  摘要：

  Ethoxy vinyl esters (EVE:2) were efficient reagents for promoting the asymmetric Pummerer reaction with high enantioselectivity and high yield in contrast to the generally used acid anhydrides. Increasing the electron-donating ability on the R function in EVE 2 tended to increase enantioselectivity. Consequently, effective asymmetric rearrangements were achieved using EVEs 2b,c bearing a methoxybenzoyloxy function. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00510-1
• 作为产物：
  描述：

  乙氧基乙炔 、 对硝基苯甲酸 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以40%的产率得到1-ethoxyvinyl 4-nitrobenzoate
  参考文献：
  名称：

  Highly asymmetric Pummerer-type reaction induced by ethoxy vinyl esters

  摘要：

  Ethoxy vinyl esters (EVE:2) were efficient reagents for promoting the asymmetric Pummerer reaction with high enantioselectivity and high yield in contrast to the generally used acid anhydrides. Increasing the electron-donating ability on the R function in EVE 2 tended to increase enantioselectivity. Consequently, effective asymmetric rearrangements were achieved using EVEs 2b,c bearing a methoxybenzoyloxy function. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00510-1

文献信息

• Efficient Lipase-Catalyzed Enantioselective Desymmetrization of Prochiral 2,2-Disubstituted 1,3-Propanediols and Meso 1,2-Diols Using 1-Ethoxyvinyl 2-Furoate
  作者：Shuji Akai、Tadaatsu Naka、Tetsuya Fujita、Yasushi Takebe、Toshiaki Tsujino、Yasuyuki Kita

  DOI：10.1021/jo010587f

  日期：2002.1.1

  desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols was developed using 1-ethoxyvinyl 2-furoate 1b, for which the well-known method using vinyl or isopropenyl acetate has had limited success due to low reactivity and easy racemization of the products through acyl group migration. The reagent 1b is highly reactive and converts various prochiral 1,3-diols to the monoesters having a chiral quaternary

  使用1-乙氧基乙烯基2-糠酸酯1b，开发了一种有效的脂肪酶催化的手性2,2-二取代的1,3-丙二醇的脱对称化，由于其低反应性和低粘度，众所周知的使用乙烯基乙酸或异丙烯基乙酸酯的方法获得的成功有限。通过酰基迁移使产品易于消旋。试剂1b是高反应性的，并且将各种手性的1，3-二醇转化为具有手性季碳中心且ee为82-99％的单酯。这些产物在酸性条件下对外消旋作用是稳定的，它们的呋喃酰基与氧化条件相容。延长反应时间导致单酯的动力学拆分，从而导致其光学纯度的提高。内消旋顺式1,2-环烷二醇的相似脱对称得到单酯，其ee为82-97％，没有消旋化。
• Highly asymmetric Pummerer-type reaction induced by ethoxy vinyl esters
  作者：Norio Shibata、Masato Matsugi、Noriyuki Kawano、Seiji Fukui、Chino Fujimori、Kentoku Gotanda、Kenji Murata、Yasuyuki Kita

  DOI：10.1016/s0957-4166(96)00510-1

  日期：1997.1

  Ethoxy vinyl esters (EVE:2) were efficient reagents for promoting the asymmetric Pummerer reaction with high enantioselectivity and high yield in contrast to the generally used acid anhydrides. Increasing the electron-donating ability on the R function in EVE 2 tended to increase enantioselectivity. Consequently, effective asymmetric rearrangements were achieved using EVEs 2b,c bearing a methoxybenzoyloxy function. (C) 1997 Elsevier Science Ltd.