N-苄基-1-(3,5-二甲氧基苯基)甲亚胺 | 148171-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基-1-(3,5-二甲氧基苯基)甲亚胺
• 英文名称: 3,5-dimethoxybenzylidenebenzylamine
• 英文别名: (E)-N-Benzyl-1-(3,5-dimethoxyphenyl)methanimine；N-benzyl-1-(3,5-dimethoxyphenyl)methanimine
• CAS: 148171-51-1
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: AWSKYUVSKHULDP-UHFFFAOYSA-N

物化性质

• 沸点：
  403.6±45.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  N-苄基-1-(3,5-二甲氧基苯基)甲亚胺 在 硫酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 Methyl 3-(benzylamino)-2,2-dideuterio-3-(3,5-dimethoxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis of α,α-dideutero-β-amino esters

  摘要：

  A straight forward entry to alpha,alpha-dideutero-beta-amino esters starting from the corresponding imines and deuterated acetonitrile has been developed involving a two-step process. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.004
• 作为产物：
  描述：

  N-苄基-1-(4-溴苯基)甲亚胺 在 硫酸 、 palladium on activated charcoal 、 甲酸铵 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 N-苄基-1-(3,5-二甲氧基苯基)甲亚胺
  参考文献：
  名称：

  Synthesis of α,α-dideutero-β-amino esters

  摘要：

  A straight forward entry to alpha,alpha-dideutero-beta-amino esters starting from the corresponding imines and deuterated acetonitrile has been developed involving a two-step process. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.004

文献信息

• Asymmetric aza-Diels-Alder reaction: enantio- and diastereoselective reaction of imine mediated by Chiral Lewis acid
  作者：Kouji Hattori、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)80532-9

  日期：1993.2

  asymmetric aza-Diels-Alder reaction using chiral boron mediator is developed. The key to its success is the use of the chiral boron complex prepared in situ from (R)- or (S)- binaphthol and B(OPh)3. The enantiomeric reaction of prochiral imine affords products of up to 90% ee. The double asymmetric induction of chiral imine using α-benzylamine as a chiral auxiliary is achieved with almost complete diastereoselectivity

  开发了一种有效的使用手性硼介体的不对称aza-Diels-Alder反应。其成功的关键是使用由（R）-或（S）-联萘酚和B（OPh）3原位制备的手性硼配合物。前手性亚胺的对映体反应可提供高达90％ee的产物。使用α-苄基胺作为手性助剂，可以实现对脂肪族和芳香族亚胺几乎完全非对映选择性的手性亚胺的双不对称诱导。该方法适用于高效合成哌啶生物碱的鸟嘌呤和芥氨酸。
• An Air Stable Moisture Resistant Titanium Triflate Complex as a Lewis Acid Catalyst for CC Bond Forming Reactions
  作者：Steven D. Bull、Matthew G. Davidson、Andrew L. Johnson、Mary F. Mahon、Diane E. J. E. Robinson

  DOI：10.1002/asia.200900305

  日期：2010.3.1

  An air and moisture stable C3‐symmetric titanium(IV) triflate, supported by a tripodal amine‐(tris‐phenolate) ligand, has been synthesized and characterized by X‐ray crystallography and shown to be a good Lewis acid catalyst for a range of aza‐Diels–Alder, Diels–Alder, syn aldol, allylation, and alkylation reactions.

  由X射线晶体学合成并表征了一种空气和湿气稳定的C 3对称的三氟甲磺酸三氟甲磺酸钛（IV），并通过X射线晶体学对其进行了表征，显示出在一定范围内是很好的路易斯酸催化剂的氮杂-Diels-桤木，狄尔斯-阿德耳，顺式羟醛，烯丙基化，和烷基化反应。
• From Nature to Synthetic Compounds: Novel 1(N),2,3 Trisubstituted-5-oxopyrrolidines Targeting Multiple Myeloma Cells
  作者：Roberta Listro、Alessio Malacrida、Francesca Alessandra Ambrosio、Giacomo Rossino、Marcello Di Giacomo、Valeria Cavalloro、Martina Garbagnoli、Pasquale Linciano、Daniela Rossi、Guido Cavaletti、Giosuè Costa、Stefano Alcaro、Mariarosaria Miloso、Simona Collina

  DOI：10.3390/ijms232113061

  日期：——

  The insurgence of drug resistance in treating Multiple Myeloma (MM) still represents a major hamper in finding effective treatments, although over the past decades new classes of drugs, such as proteasome inhibitors and immunomodulatory drugs, have been discovered. Recently, our research team, within a Nature-Aided Drug Discovery project, isolated from Hibiscus Sabdariffa L. calyces the secondary metabolite called Hib-ester which possesses antiproliferative properties against human multiple myeloma RPMI 8226 cells, reduces migration and cell invasion and inhibits proteasome without neurotoxic effects. In the present study, we explored the chemical spaces of the hit compound Hib-ester. We explored the structure-activity relationships (SAR), and we optimized the scaffold through sequentially modifying Hib-ester subunits. Compound screening was performed based on cytotoxicity against the RPMI 8226 cells to assess the potential efficacy toward human MM. The ability of the most effective molecules to inhibit the proteasome was evaluated and the binding mode of the most promising compounds in the proteasome chymotrypsin binding pocket was deciphered through molecular modeling simulations. Compounds 13 and 14 are more potent than Hib-ester, demonstrating that our strategy was suitable for the identification of a novel chemotype for developing possible drug candidates and hopefully widening the drug armamentarium against MM.

  过去几十年来，虽然蛋白酶体抑制剂和免疫调节药物等新药不断被发现，但治疗多发性骨髓瘤（MM）的抗药性问题仍然是找到有效治疗方法的主要障碍。最近，我们的研究团队在一个自然辅助药物发现项目中，从木槿萼片中分离出了一种名为 Hib-ester 的次级代谢产物，它具有抗人多发性骨髓瘤 RPMI 8226 细胞增殖的特性，能减少细胞迁移和侵袭，并能抑制蛋白酶体，且无神经毒性作用。在本研究中，我们探索了命中化合物 Hib-ester 的化学空间。我们探索了结构-活性关系（SAR），并通过连续修饰 Hib-ester 亚基优化了支架。根据对 RPMI 8226 细胞的细胞毒性进行了化合物筛选，以评估对人类 MM 的潜在疗效。评估了最有效分子抑制蛋白酶体的能力，并通过分子建模模拟破译了最有希望的化合物在蛋白酶体糜蛋白酶结合袋中的结合模式。化合物 13 和 14 比 Hib-ester 更有效，这表明我们的策略适用于鉴定新的化学类型，以开发可能的候选药物，并有望扩大抗 MM 的药物范围。
• Steric and electronic effects on the regioselective formation of platinum(II) metallacycles: crystal structure of [PtMe(3-MeC6H3CHNCH2C6H5)(PPh3)]
  作者：Margarita Crespo、Xavier Solans、Mercè Font-Bardía

  DOI：10.1016/0022-328x(96)83109-3

  日期：1996.2

  The reaction of [Pt(2)Me(4)(mu-SMe(2))(2)] (1) with imines 3,4-(OMe)(2)C6H3CH=NCH(2)Ph (2c) and 3-MeC(6)H(6)CH=NCH(2)Ph (2e) yields cyclometallated compounds [PtMe(3,4-(OMe)(2)C6H2CH=NCH(2)Ph)(SMe(2))] (4c) and [PtMe(3-MeC(6)H(3)CH=NCH(2)Ph)(SMe(2))] (4e) arising from selective metallation at the less hindered of the two non-equivalent ortho positions of the aryl ring, followed by loss of methane. These compounds react with PPh(3) to give cyclometallated compounds [PtMe(3,4-(OMe)(2)C6H2CH=NCH(2)Ph)(PPh(3))] (5c) and [PtMe(3-MeC(6)H(3)CH=NC(2)Ph)(PPh(3))] (5e). Imines 2,4,6-(OMe)(3)C6H2CH=NCH(2)Ph (2a), 3,5-(OMe)(2)C6H3CH=NCH(2)Ph (2b) and 2,5-Me(2)C(6)H(3)CH=NCH(2)Ph (2d) coordinate to platinum through the nitrogen atom to yield compounds [PtMe(2)(ArCH=NCH(2)Ph)(SMe(2))] (3) but fail to produce cyclometallated compounds.
• 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.