N-4-methylbenzyl furfurylamine

• 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-4-methylbenzyl furfurylamine
• 英文别名: Furan-2-ylmethyl-(4-methyl-benzyl)-amine；N-(furan-2-ylmethyl)-1-(4-methylphenyl)methanamine
• 化学式: C₁₃H₁₅NO
• mdl: MFCD03110580
• 分子量: 201.268
• InChiKey: LTKSRIGURQCUJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-4-methylbenzyl furfurylamine 在 sodium tetrachloropalladate(II) 、 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 水 、 丙酮 、 乙腈 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Palladium meditated CPhenyl–H bond activation of 2-furylimines versus tert-2-furylbenzylamines

  摘要：

  The reactions of 2-furylimines 2a-f and Na2PdCl4 in the presence of NaOAc at 8-10 degrees C result in nitrogen-palladium coordinated complexes 3a-f. Reduction of 2d-f with NaBH4 followed by N-methylation leads to the corresponding tert-2-furylbenzylamines 5a-c. Treatment of 5a-c with Na2PdCl4 at the same reaction condition as mentioned above affords palladacycles 6a-c where the Pd atoms connect to the phenyl ring rather than the furyl ring. The fact that 5a-c are more active than 2d-f in C-Phenyl-H bond activation implies that the electron density of C10 or C8 atom in former is higher than those in latter. Compounds 3a-f, 5a-c, 6a-c were identified by elemental analysis, IR and NMR. In addition, the structures of 3b, 3f and 6c were also confirmed by their single crystal X-ray diffractions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.041
• 作为产物：
  描述：

  4-甲基苄胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 N-4-methylbenzyl furfurylamine
  参考文献：
  名称：

  Palladium meditated CPhenyl–H bond activation of 2-furylimines versus tert-2-furylbenzylamines

  摘要：

  The reactions of 2-furylimines 2a-f and Na2PdCl4 in the presence of NaOAc at 8-10 degrees C result in nitrogen-palladium coordinated complexes 3a-f. Reduction of 2d-f with NaBH4 followed by N-methylation leads to the corresponding tert-2-furylbenzylamines 5a-c. Treatment of 5a-c with Na2PdCl4 at the same reaction condition as mentioned above affords palladacycles 6a-c where the Pd atoms connect to the phenyl ring rather than the furyl ring. The fact that 5a-c are more active than 2d-f in C-Phenyl-H bond activation implies that the electron density of C10 or C8 atom in former is higher than those in latter. Compounds 3a-f, 5a-c, 6a-c were identified by elemental analysis, IR and NMR. In addition, the structures of 3b, 3f and 6c were also confirmed by their single crystal X-ray diffractions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.041

文献信息

• Synthetic bioregulators of poly-cis carotenoid biosynthesis
  作者：Stephen M. Poling、Wan-Jean Hsu、Henry Yokoyama

  DOI：10.1016/0031-9422(82)83148-8

  日期：——

  to induce the biosynthesis of poly- cis carotenes in the flavedo of Marsh white seedless grapefruit. The effects of these new bioregulators are the same as that of the previously reported dibenzylamines, but several of the new compounds are more effective and cause the accumulation of up to 162 μg/g dry wt of poly- cis carotenes in the flavedo as compared to the maximum of 74 μg/g dry wt observed previously

  摘要 合成了 17 种新的生物调节剂，并测试了它们在沼泽白无籽葡萄柚果皮中诱导多顺式胡萝卜素生物合成的能力。这些新的生物调节剂的作用与之前报道的二苄胺的作用相同，但有几种新化合物更有效，与相比之下，在 flavedo 中积累了高达 162 μg/g 干重的多顺式胡萝卜素。先前观察到的最大值为 74 μg/g 干重。测试的化合物是取代的N-苄基糠胺、N-苄基、N-甲基糠胺和N-烷基、N-甲基苄胺。它们证明了叔胺和仲胺刺激多顺式胡萝卜素形成的能力。N-(4-溴苄基)糠胺的相互作用，一种更有效的新化合物，
• Nickel-catalyzed hydrogenative coupling of nitriles and amines for general amine synthesis
  作者：Vishwas G. Chandrashekhar、Wolfgang Baumann、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1126/science.abn7565

  日期：2022.6.24

  Efficient and general methods for the synthesis of amines remain in high demand in the chemical industry. Among the many known processes, catalytic hydrogenation is a cost-effective and industrially proven reaction and currently used to produce a wide array of such compounds. We report a homogeneous nickel catalyst for hydrogenative cross coupling of a range of aromatic, heteroaromatic, and aliphatic

  合成胺的有效和通用方法在化学工业中仍然有很高的需求。在许多已知的方法中，催化加氢是一种经济有效且经工业验证的反应，目前用于生产多种此类化合物。我们报告了一种均相镍催化剂，用于将一系列芳族、杂芳族和脂肪族腈与伯胺和仲胺或氨进行氢化交叉偶联。该通用氢化方案通过直接和高选择性合成 > 230 种功能化和结构多样的胺（包括药学相关和手性产物）以及15N-同位素标记应用。
• Synthesis of renewable isoindolines from bio-based furfurals
  作者：Feng Xu、Zao Li、Li-long Zhang、Shengqi Liu、Hu Li、Yuhe Liao、Song Yang

  DOI：10.1039/d2gc04786a

  日期：——

  Upgrading biomass-derived platforms to functionalized aromatics by a tandem Diels–Alder (DA) cycloaddition–aromatization strategy has attracted broad attention. However, three challenges exist: improving the equilibrium of DA cycloaddition, controlling the regioselectivity of DA adducts, and increasing the stability of the cycloadduct. Herein, an intramolecular cycloaromatization strategy was developed

  通过串联 Diels-Alder (DA) 环加成-芳构化策略将生物质衍生平台升级为功能化芳烃引起了广泛关注。然而，存在三个挑战：改善DA环加成的平衡、控制DA加合物的区域选择性和增加环加合物的稳定性。在此，开发了一种分子内环芳构化策略，用于在液相条件下通过选择性形成exo -DA 加合物将生物糠醛直接升级为异吲哚啉酮。有缺陷的 Zn-BTC-SA 催化剂定量形成所需的区域选择性外显子显着提高了分子内 DA 环加成的效率-具有更高热稳定性的DA环加合物。同时，酸性离子液体([Hmim]HSO 4 )的共存可以促进后续芳构化生成定量收率的异吲哚啉酮。理论计算阐述了原位形成的exo -DA 加合物在级联转化过程中具有增强稳定性的重要性。此外，该协议适用于生产范围广泛的可再生异吲哚啉酮衍生物和商业药物，产量极佳（> 92%），适用于克级反应。