N-benzyl-N-3,4-dimethoxybenzylimine | 33859-00-6

• 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-benzyl-N-3,4-dimethoxybenzylimine
• 英文别名: N-benzyl-(3,4-dimethoxyphenyl)methanimine；N-benzyl-1-(3,4-dimethoxyphenyl)methanimine
• CAS: 33859-00-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: DFLJPXRIJLPIOX-UHFFFAOYSA-N

物化性质

• 熔点：
  55 °C
• 沸点：
  204-209 °C(Press: 2 Torr)
• 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-benzyl-N-3,4-dimethoxybenzylimine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以2.5 g的产率得到苄基-(3,4-二甲氧基苄基)胺
  参考文献：
  名称：

  Simple Synthetic Equivalents for the β-(N,N-Disubstituted)ethylamino Acyl Cation Synthon and their Applications

  摘要：

  合成了多种N,N-二取代的β-氨基-N-甲氧基-N-甲基丙酰胺3a-i，它们作为优秀的β-氨基酰基阳离子等价物。这些化合物被用于制备β-氨基酮1，具有药理活性的三级1-(3,3-二芳基丙基)胺7a-c，以及有趣的C-糖苷8。

  DOI：

  10.1055/s-2001-18439
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 苄胺 以 苯 为溶剂， 反应 2.0h， 生成 N-benzyl-N-3,4-dimethoxybenzylimine
  参考文献：
  名称：

  Simple Synthetic Equivalents for the β-(N,N-Disubstituted)ethylamino Acyl Cation Synthon and their Applications

  摘要：

  合成了多种N,N-二取代的β-氨基-N-甲氧基-N-甲基丙酰胺3a-i，它们作为优秀的β-氨基酰基阳离子等价物。这些化合物被用于制备β-氨基酮1，具有药理活性的三级1-(3,3-二芳基丙基)胺7a-c，以及有趣的C-糖苷8。

  DOI：

  10.1055/s-2001-18439

文献信息

• Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand as an auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol
  作者：Xiaozhong Chen、Yao Ai、Peng Liu、Chenchen Yang、Jiazhi Yang、Feng Li

  DOI：10.1016/j.jcat.2021.08.037

  日期：2021.10

  A Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand was designed, synthesized, and found to be a general and efficient auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol as both hydrogen source and methylating reagent. In the presence of [Cp*Ir(2,2′-CH2BiBzImH2)Cl][Cl], a range

  设计、合成了带有柔性桥接和功能性 2,2'-亚甲基联苯并咪唑配体的 Cp*Ir 配合物，并发现它是一种通用且高效的自串联催化剂，用于通过转移氢化从亚胺合成 N-甲基叔胺/N-甲基化用甲醇作为氢源和甲基化试剂。在 [Cp*Ir(2,2'-CH 2 BiBzImH 2 )Cl][Cl] 存在下，以高收率和几乎完全的选择性获得了一系列理想的产物。由于高度的原子经济性以及最少的化学品和能源消耗，该反应极具吸引力。值得注意的是，这项研究展示了金属-配体双功能催化剂在活化甲醇作为有机合成的 C1 来源方面的新潜力。
• Chiral Bis-π-allylpalladium Complex Catalyzed Asymmetric Allylation of Imines:  Enhancement of the Enantioselectivity and Chemical Yield in the Presence of Water
  作者：Rodney A. Fernandes、Anton Stimac、Yoshinori Yamamoto

  DOI：10.1021/ja037272x

  日期：2003.11.1

  The chiral pi-allylpalladium complex 2a, prepared from exoethylidenenorpinane 7, catalyzed the allylation of diverse imines with allyltributylstannane in the presence of 1 equiv of water in good to high enantioselectivities. The catalyst prepared from a 1:1 mixture of (E)- and (Z)-7 was found to be consisting of two stereoisomers 2a and 2b in 1.3:1 ratio. On separation, 2a catalyzed the allylation of

  由外亚乙基去甲茚烷 7 制备的手性 pi-烯丙基钯配合物 2a 在 1 当量水存在下以良好到高的对映选择性催化各种亚胺与烯丙基三丁基锡烷的烯丙基化。发现由(E)-和(Z)-7的1:1混合物制备的催化剂由比例为1.3:1的两种立体异构体2a和2b组成。分离时，2a 以比 2b 高得多的对映选择性催化亚胺烯丙基化，产生相同的主要对映异构体，从而证明需要分离不含 2b 的 2a。我们通过反复重结晶实现了 2a:2b 的最高分离比 >400:1。观察到在从滤液中回收 2a 期间 2b 异构化为 2a，因为在重结晶期间每次回收更多的 2a。虽然干 THF 是最好的溶剂，我们尝试了各种添加剂，发现加入一当量的水在更短的反应时间、更高的产率和对映选择性方面得到了最好的结果。因此，我们开发了一种更通用的、可重复的、稳健的和非路易斯酸催化的程序，用于在基本中性条件下催化亚胺的不对称烯丙基化。
• Coordination attitude of benzothiazole hydrazone in ruthenium(II) complexes: Catalytic applications on direct formation of imines via acceptorless dehydrogenative process
  作者：Subbarayan Vijayapritha、Periasamy Viswanathamurthi、Paranthaman Vijayan

  DOI：10.1016/j.ica.2023.121523

  日期：2023.8

  [Ru(L1-3)(CO)(PPh3)2]Cl or [Ru(L4-5)H(CO)(PPh3)2] [L1 = (salicyl((2-(benzothiazol-2yl)hydrazono)methylphenol)) (SAL-HBT), L2 = 2-((2-(benzothiazol-2-yl)hydrazono)methyl)-6 methoxyphenol) (VAN-HBT), L3 = naphtyl-2-((2-(benzothiazol-2-yl)hydrazono)methylphenol) (NAP-HBT), L4 = 1-((benzothiazol-2-yl)-2-(furan-2-ylmethylene)hydrazine) (FUR-HBT) or L5 = 1-((benzothiazol-2-yl)-2-(thiophen-2 ylmethylene)hydrazine) (THI-HBT)]

  新的 Ru(II) 配合物 ( 1 – 5 ) 包含 [Ru(L 1-3 )(CO)(PPh 3 ) 2 ]Cl 或 [Ru(L 4-5 )H(CO)(PPh 3 )类腙) 2 ] [L 1 = (水杨基((2-(苯并噻唑-2基)亚肼基)甲基苯酚)) (SAL-HBT), L 2 = 2- (  (2-(苯并噻唑-2-基)亚肼基)甲基)- 6 甲氧基苯酚) (VAN-HBT), L 3  = naphtyl-2-((2-(benzothiazol-2-yl)hydrazono)methylphenol) (NAP-HBT), L 4 = 1-( (  benzothiazol-2-yl) -2-(呋喃-2-基亚甲基)肼) (FUR-HBT) 或 L 5= 1-((benzothiazol-2-yl)-2-(thiophen-2ylmethylene)hydrazine) (THI-HBT)]
• Resistance-Modifying Agents. 11. Pyrimido[5,4-<i>d</i>]pyrimidine Modulators of Antitumor Drug Activity. Synthesis and Structure−Activity Relationships for Nucleoside Transport Inhibition and Binding to α₁-Acid Glycoprotein
  作者：Nicola J. Curtin、Hannah C. Barlow、Karen J. Bowman、A. Hilary Calvert、Richard Davison、Bernard T. Golding、Bing Huang、Peter J. Loughlin、David R. Newell、Peter G. Smith、Roger J. Griffin

  DOI：10.1021/jm040772w

  日期：2004.9.1

  The cardiovascular and antithrombotic agent dipyridamole (DP) has potential therapeutic utility as a modulator of the activity of antimetabolite antitumor agents by virtue of its inhibition of nucleoside transport. However, the activity of DP can be compromised by binding to the acute phase serum protein, alpha(1)-acid glycoprotein (AGP). Analogues of DP were synthesized and evaluated as inhibitors of H-3-thymidine uptake into L1210 leukamia cells in the presence and absence of 5 mg/mL AGP. Compounds with potency similar to that of DP were identified where the piperidino substituents at the 4,8-positions were replaced by 4'-methoxybenzylamino, 3',4'dimethoxybenzylamino, or piperonylamino groups. Replacement of the diethanolamino groups at the 2,6-positions of DP by alkylamino or alkoxy substituents was tolerated, although at least one oxygen-bearing function (hydroxyl or alkoxy) was required in the side chain for activity comparable to that of DP. Whereas AGP completely ablated the activity of DP, the majority of the newer compounds synthesized retained significant activity in the presence of excess AGP, although replacement of the piperidino groups at the 4,8-positions by N-methylbenzylamino substituents did, in some cases, restore susceptibility to AGP. Selected compounds have been demonstrated to prevent rescue from antifolate cytotoxicity, mediated by nucleoside salvage.
• 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.