N-(p-Phenoxybenzal)-anilin | 41616-59-5

• 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: N-(p-Phenoxybenzal)-anilin
• 英文别名: (4-phenoxy-benzyliden)-aniline；4-Phenoxy-benzaldehyd-phenylimin；(4-Phenoxy-benzyliden)-anilin；(4-Phenoxy-benzylidene)-phenyl-amine；1-(4-phenoxyphenyl)-N-phenylmethanimine
• CAS: 41616-59-5
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: PBEQUZNFMPJFMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(p-Phenoxybenzal)-anilin 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 N-(4-phenoxybenzyl)aniline
  参考文献：
  名称：

  Discovery of liver selective non-steroidal glucocorticoid receptor antagonist as novel antidiabetic agents

  摘要：

  Series of benzyl-phenoxybenzyl amino-phenyl acid derivatives (8a-q) are reported as non-steroidal GR antagonist. Compound 8g showed excellent h-GR binding and potent antagonistic activity (in vitro). The lead compound 8g exhibited significant oral antidiabetic and antihyperlipidemic effects (in vivo), along with liver selectivity. These preliminary results confirm discovery of potent and liver selective passive GR antagonist for the treatment of T2DM. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.078
• 作为产物：
  描述：

  4-甲基二苯基醚 在 potassium permanganate 、 Pd-BaSO₄ 、 五氯化磷 、 水 、 甲苯 作用下， 生成 N-(p-Phenoxybenzal)-anilin
  参考文献：
  名称：

  Lock; Kempter, Monatshefte fur Chemie, 1936, vol. 67, p. 24,35

  摘要：

  DOI：

文献信息

• Anil-Synthese. 3. Mitteilung [1] Über die Darstellung von Styryl-Derivaten aus methyl-substituierten carbocyclischen Aromaten
  作者：A. E. Siegrist、P. Liechti、H. R. Meyer、K. Weber

  DOI：10.1002/hlca.19690520836

  日期：——

  1,4-Diphenylbutadien-, Tolan-, 1,4-Diphenylbutadiin-, Naphtalin-, Anthracen-und Phenanthren-Reihe werden mit Anilen aromatischer Aldehyde in Dimethylformamid in Gegenwart von Kaliumhydroxid oder Kalium-t-butylat zu Styryl-Derivaten umgesetzt.

  甲基取代碳环芳烃，二苯基，三联苯，Stilben-，1,4-二苯基丁二烯-，Tolan-，1,4-二苯基丁二烯-，萘酚-，蒽环与苯并蒽-苯并二氮杂-苯并二氢萘Gegenwart von Kaliumhydroxid oder Kal-叔丁基中的二甲基甲酰胺。
• Acceptorless dehydrogenative construction of CN and CC bonds through catalytic aza-Wittig and Wittig reactions in the presence of an air-stable ruthenium pincer complex
  作者：Nandita Biswas、Kalicharan Das、Bitan Sardar、Dipankar Srimani

  DOI：10.1039/c8dt04725a

  日期：——

  aza-Wittig type reaction. The reaction is catalyzed by an acridine-derived ruthenium pincer complex and does not use any oxidant. The present protocol offers a wide substrate scope, including aliphatic, aryl or heteroaryl alcohol/azides. This expeditious protocol was successfully applied to construct a CC bond directly from alcohol via dehydrogenative Wittig reaction. Furthermore, the synthesis of structurally

  C N键的构建是通过aza-Wittig型反应将醇与叠氮化物进行脱氢偶联而实现的。该反应由an啶衍生的钌钳配合物催化，并且不使用任何氧化剂。本协议提供了广泛的底物范围，包括脂族，芳基或杂芳基醇/叠氮化物。该快速方案已成功应用于通过脱氢Wittig反应直接从醇中构建C C键。此外，通过该方法还可以合成结构上重要的吡咯并[1,4]苯并二氮杂衍生物。
• Separation of Ring Polar and Resonance Effects on the Rate and Equilibrium Constants for Methoxide Ion-Promoted Addition of Methanol to N-Benzylideneanilines Substituted at the Benzylidene Moiety
  作者：Jean Toullec、Sadjia Bennour

  DOI：10.1021/jo00089a032

  日期：1994.5

  Rate and equilibrium constants for the title reaction (alpha-amino ether formation) at 25 degrees C in methanol are reported for 16N-benzylideneanilines (BAs) substituted at the benzaldehyde moiety. In contrast, to a previous report dealing with BAs substituted at the aniline residue, it is shown that an uncatalyzed pathway competes with the methoxide ion-catalyzed reaction, these two processes corresponding to rate-limiting attachment of the lyate ion to the C=N bond of iminium ion and free imine, respectively. For the latter reaction pathway, the lifetimes of the amide-ion intermediates are long enough to allow a stepwise mechanism. The equilibrium constants for the overall reaction are correlated by the two-parameter Young-Jencks (YJ) equation [log K or log k = rho(n) sigma(n) + rho(n) sigma(n) + C] allowing separation of the overall polar effect of the substituted ring (p(n) = 0.87), including resonance-induced polar (RP) effects, from the direct resonance (DR) effect due to conjugation with the C=N group (p(r) = 0.54). For the forward methoxide ion-catalyzed process, the polar and DR contributions to the substituent effects on the second-order rate constant have the same sign (p(n) = 1.79 and p(r) = 0.28, respectively), but these have opposite signs (p(n) = 0.92 and p(r) = -0.25) for the reverse reaction. The contribution of the DR effects for the reverse rate constants, which make the points lie above the log k-sigma(n) line, stems from gain in resonance at the negatively charged transition state. The validity and significance of the YJ treatment are discussed.
• Lock; Kempter, Monatshefte fur Chemie, 1936, vol. 67, p. 24,35
  作者：Lock、Kempter

  DOI：——

  日期：——
• Discovery of liver selective non-steroidal glucocorticoid receptor antagonist as novel antidiabetic agents
  作者：Kiran Shah、Dipam Patel、Pradip Jadav、Mubeen Sheikh、Kalapatapu V.V.M. Sairam、Amit Joharapurkar、Mukul R. Jain、Rajesh Bahekar

  DOI：10.1016/j.bmcl.2012.07.078

  日期：2012.9

  Series of benzyl-phenoxybenzyl amino-phenyl acid derivatives (8a-q) are reported as non-steroidal GR antagonist. Compound 8g showed excellent h-GR binding and potent antagonistic activity (in vitro). The lead compound 8g exhibited significant oral antidiabetic and antihyperlipidemic effects (in vivo), along with liver selectivity. These preliminary results confirm discovery of potent and liver selective passive GR antagonist for the treatment of T2DM. (C) 2012 Elsevier Ltd. All rights reserved.