1-(furan-2-yl)-N-(4-methoxyphenyl)methanimine | 1749-14-0

• 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-(furan-2-yl)-N-(4-methoxyphenyl)methanimine
• 英文别名: N-furfurylidene-p-anisidine
• CAS: 1749-14-0；100239-11-0
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: WAWJOIUQEZYIAH-LCYFTJDESA-N

物化性质

• 沸点：
  331.8±22.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.73
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(furan-2-yl)-N-(4-methoxyphenyl)methanimine 在 三乙胺 作用下， 以 phosphate buffer 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 (3S,4S)-(-)-4-(furan-2-yl)-3-hydroxy-1-(4-methoxyphenyl)-2-azetidinone
  参考文献：
  名称：

  Arthrobacter sp.: a lipase of choice for the kinetic resolution of racemic arylazetidinone precursors of taxanoid side chains

  摘要：

  The native strain of Arthrobacter sp. (MTCC 5125) bearing a lipase has been found to be the most effective in the kinetic resolution of racemic arylazetidinones for producing cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone, cis-(3R,4R)-3acetoxy-1-(4-methoxyphenyl)-4-(2-furanyl)-2-azetidinone, cis-(3R,4R)-3-acetoxy-1-(4-methoxyphenyl)-4-(2-thienyl)-2-azetidinone, and cis-3-acetoxy-4-(t-butyl)-2-azetidinone products. The resolved compounds, which were obtained in high enantiopurity are important intermediates of amino acid side chains of paclitaxel as well as a new generation of taxanoids. The use of co-solvents dramatically improved the resolution efficacy of the lipase. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.031
• 作为产物：
  描述：

  糠醛 、 甲氧苯胺 以 甲苯 为溶剂， 生成 1-(furan-2-yl)-N-(4-methoxyphenyl)methanimine
  参考文献：
  名称：

  Arthrobacter sp.: a lipase of choice for the kinetic resolution of racemic arylazetidinone precursors of taxanoid side chains

  摘要：

  The native strain of Arthrobacter sp. (MTCC 5125) bearing a lipase has been found to be the most effective in the kinetic resolution of racemic arylazetidinones for producing cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone, cis-(3R,4R)-3acetoxy-1-(4-methoxyphenyl)-4-(2-furanyl)-2-azetidinone, cis-(3R,4R)-3-acetoxy-1-(4-methoxyphenyl)-4-(2-thienyl)-2-azetidinone, and cis-3-acetoxy-4-(t-butyl)-2-azetidinone products. The resolved compounds, which were obtained in high enantiopurity are important intermediates of amino acid side chains of paclitaxel as well as a new generation of taxanoids. The use of co-solvents dramatically improved the resolution efficacy of the lipase. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.031

文献信息

• A convenient synthesis of α-amino-β-lactams
  作者：Ajay K. Bose、M.S. Manhas、J.M. van der Veen、S.G. Amin、I.F. Fernandez、K. Gala、R. Gruska、J.C. Kapur、M.S. Khajavi、J. Kreder、L. Mukkavilli、B. Ram、M. Sugiura、J.E. Vincent

  DOI：10.1016/s0040-4020(01)88885-2

  日期：1981.1

  A safe and convenient method is described for the synthesis of α-amido-β-lactams starting with glycine and an azomethine. The amino group of glycine is protected by reaction with a β-dicarbonyl compound following the method of Dane etal. and the carboxyl group is activated through the formation of a mixed anhydride or an active ester. Condensation between these glycine derivatives and acyclic or cyclic

  描述了一种安全，方便的方法，用于从甘氨酸和偶氮甲碱开始合成α-酰胺基-β-内酰胺。按照Dane等人的方法，通过与β-二羰基化合物反应来保护甘氨酸的氨基。羧基通过形成混合酸酐或活性酯而被活化。在三乙胺存在下，这些甘氨酸衍生物与无环或环状亚氨基化合物（包括硫代亚氨酸酯）之间的缩合导致3-（β-羰基-乙烯基氨基）-2-氮杂环丁酮的立体定向合成，产率为40-60％。乙烯基氨基侧链可在弱酸条件下水解形成3-氨基-2-氮杂环丁酮，其可被酰化为α-酰胺基-β-内酰胺。或者，可以通过臭氧分解将乙烯基氨基侧链转化为酰胺侧链。通过X射线晶体学测定3-（β-羰基-乙烯基氨基）-2-氮杂环丁酮的分子参数。通过制备同位素标记的β-内酰胺和某些β-内酰胺抗生素的中间体，可以说明这种α-酰胺基-β-内酰胺合成的有用性。
• Prajapati, Dipak; Attaluri, Sivaprasad; Sandhu, Jagir S., Heterocycles, 1984, vol. 22, # 5, p. 1005 - 1006
  作者：Prajapati, Dipak、Attaluri, Sivaprasad、Sandhu, Jagir S.、Baruah, Jogendra Nath

  DOI：——

  日期：——
• ALCAIDE, BENITO;PLUMET, JOAQUIN;RODRIGUEZ-LIPEZ, JULIAN;SANCHEZ-CANTALEJO+, TETRAHEDRON LETT., 31,(1990) N7, C. 2493-2496
  作者：ALCAIDE, BENITO、PLUMET, JOAQUIN、RODRIGUEZ-LIPEZ, JULIAN、SANCHEZ-CANTALEJO+

  DOI：——

  日期：——