3,4-Dimethoxy-benzalanilin | 166670-25-3

• 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: 3,4-Dimethoxy-benzalanilin
• 英文别名: 1-(3,5-dimethoxyphenyl)-N-phenylmethanimine
• CAS: 166670-25-3
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: SWWCTFZPOUSIQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Dimethoxy-benzalanilin 以 氘代氯仿 、 溶剂黄146 为溶剂， 生成
  参考文献：
  名称：

  Cyclometallation of 3,5 disubstituted N-benzylideneamines by palladium(II). Synthesis and X-ray crystal structure of [Pd(3,5-F2C6H2CHNC6H5)Br(PPh3)2]

  摘要：

  The action of Pd(AcO)(2) on the imines C6R(5 . m)CH=N(CH2)(n)C6H5 have been studied. Five-membered endo metallacyles were obtained from the imines 1a (R=3,5-F-2, n=0), 1b (R=3,5-F-2, n=1), 1c (R=3,5-(MeO)(2), n=0) and 1d (R=3,5-(MeO)(2), n=1), by activation of a O(aromatic)-H bond, in spite of the presence of MeO or F substituents on the carbon atom adjacent to the metallation H-1 NMR spectra of the acetate bridged compounds [{Pd(C-N)(mu-AcO)}(2)] (2a-d) obtained show the existence of different isomers in solution. Complexes [PdBr(C-N)(PPh(3))] (4) and [PdBr(C-N)(PPh(3))(2)] (5) can be obtained by the action of PPh(3) on the new cyclometallated compounds. [Pd(3,5-F2C6H2CH=NC6H5)Br(PPh(3))(2)] crystallizes in the space group P2(1)/a with a=20.224(4), b=17.447(3), c=12.290(2) Angstrom, beta=110.12(3)degrees and Z=4. The dihedral angle between the metallated phenyl ring and the coordination plane is 86.6 degrees. An N=CH proton and a fluorine atom ortho to the Pd-C bond occupy the apical positions in the coordination sphere of the palladium atom.

  DOI：

  10.1016/0022-328x(94)05365-i
• 作为产物：
  描述：

  苯基脲 、 3-(3,5-dimethoxyphenyl)-1-phenylprop-2-en-1-one 在 potassium hydroxide 作用下， 反应 24.0h， 以81%的产率得到3,4-Dimethoxy-benzalanilin
  参考文献：
  名称：

  通过C–C和C C键断裂， 碱催化的酰胺和亚胺合成†

  摘要：

  已经开发了一种通过C–C和C C键活化形成C–N键的过渡金属游离碱催化方法。所述Ñ -arylureas与1,3-二羰基和α，β不饱和酮反应顺利分别在温和，得到相应的酰胺和亚胺以优良的产率。

  DOI：

  10.1039/c4ra14234a

文献信息

• Substituent effects on the stretching vibration of C═N in multi‐substituted benzylideneanilines
  作者：Linyan Wang、Chaotun Cao、Chenzhong Cao

  DOI：10.1002/poc.3969

  日期：2019.9

  synthesized, and their infrared absorption spectra were recorded in this paper. On the basis of the stretching vibration frequencies νC═N of C═N bridging bond of 158 samples of substituted XBAYs (including 57 samples of 4,4′‐disubstituted XBAYs from reference and 101 samples of substituted XBAYs synthesized in this paper), an extensional research of substituent effects on the νC═N values from 4,4′‐disubstituted

  合成了39个3,4'/ 4,3'/ 3,3'-二取代的亚苄基苯胺（XBAYs）样品和52个多取代的XBAYs样品，并记录了它们的红外吸收光谱。根据158个取代的XBAY样品（包括参考文献中的57个4,4'-双取代的XBAY样品和101个合成的取代的XBAY样品）的C═N桥键的拉伸振动频率νC═N，进行了取代基对从4,4'-双取代XBAY到多取代XBAYs的νC═N值的扩展研究。用于量化νC═N的修正方程获得了多取代XBAY的值（如公式（3）所示）。公式（3）表明，对于多取代XBAYs的νC═N值进行定量回归分析，不能忽略Y的激发态取代基常数以及X和X之间的取代基特定的交叉相互作用效应。与等式（1）相比，等式（3）在量化替代XBAY的νC═N值方面具有更广泛的应用和更高的准确性。
• A concise route to biaryls : Formal synthesis of biaryl diamino diacid (AB segment) of vancomycin
  作者：A.V. Rama Rao、K Laxma Reddy、M Machender Reddy

  DOI：10.1016/s0040-4039(00)73314-4

  日期：1994.7
• Indium-catalyzed allylation of imines with electrochemically assisted catalyst regeneration
  作者：Gerhard Hilt、Konstantin I. Smolko、Christoph Waloch

  DOI：10.1016/s0040-4039(02)00044-8

  日期：2002.2

  The chemo-electrochemical regeneration of low valent indium(I) reagents for Barbier-type carbon carbon bond formation processes is described for several C N double bond systems. The homoallylic amines are obtained in good yields from aniline-derived aldimines. However, with ketimines and electron-poor aldimines. direct electrochemical or chemical reduction becomes a competing side reaction. Thus, hydrazones and sulfonimines gave almost exclusively the reduced products with only minor amounts of the allylated products being formed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Cyclometallation of 3,5 disubstituted N-benzylideneamines by palladium(II). Synthesis and X-ray crystal structure of [Pd(3,5-F2C6H2CHNC6H5)Br(PPh3)2]
  作者：Joan Albert、Jaume Granell、Rosa Moragas、Joaquim Sales、Mercè Font-Bardía、Xavier Solans

  DOI：10.1016/0022-328x(94)05365-i

  日期：1995.5

  The action of Pd(AcO)(2) on the imines C6R(5 . m)CH=N(CH2)(n)C6H5 have been studied. Five-membered endo metallacyles were obtained from the imines 1a (R=3,5-F-2, n=0), 1b (R=3,5-F-2, n=1), 1c (R=3,5-(MeO)(2), n=0) and 1d (R=3,5-(MeO)(2), n=1), by activation of a O(aromatic)-H bond, in spite of the presence of MeO or F substituents on the carbon atom adjacent to the metallation H-1 NMR spectra of the acetate bridged compounds [Pd(C-N)(mu-AcO)}(2)] (2a-d) obtained show the existence of different isomers in solution. Complexes [PdBr(C-N)(PPh(3))] (4) and [PdBr(C-N)(PPh(3))(2)] (5) can be obtained by the action of PPh(3) on the new cyclometallated compounds. [Pd(3,5-F2C6H2CH=NC6H5)Br(PPh(3))(2)] crystallizes in the space group P2(1)/a with a=20.224(4), b=17.447(3), c=12.290(2) Angstrom, beta=110.12(3)degrees and Z=4. The dihedral angle between the metallated phenyl ring and the coordination plane is 86.6 degrees. An N=CH proton and a fluorine atom ortho to the Pd-C bond occupy the apical positions in the coordination sphere of the palladium atom.
• Base-catalyzed synthesis of amides and imines via C–C and CC bond cleavage
  作者：Dilip Kumar T. Yadav、Bhalchandra M. Bhanage

  DOI：10.1039/c4ra14234a

  日期：——

  A transition metal free base catalyzed approach for C–N bond formation via C–C and CC bond activation has been developed. The N-arylureas reacted smoothly with 1,3-dicarbonyls and α,β-unsaturated ketones to furnish the corresponding amides and imines respectively in moderate to excellent yields.

  已经开发了一种通过C–C和C C键活化形成C–N键的过渡金属游离碱催化方法。所述Ñ -arylureas与1,3-二羰基和α，β不饱和酮反应顺利分别在温和，得到相应的酰胺和亚胺以优良的产率。