anti-N-<1-(furyl)ethylidene>benzylamine

• 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: anti-N-<1-(furyl)ethylidene>benzylamine
• 英文别名: (E)-N-benzyl-1-(furan-2-yl)ethan-1-imine
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: VOLYLAPEUXJFBZ-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  25.5
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  烯丙基硼酸频哪醇酯 、 anti-N-<1-(furyl)ethylidene>benzylamine 在 lanthanum(III) isopropoxide 、 氟三（三苯基膦）铜（I） 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到N-benzyl-(1-methyl-1-(2-furyl)-but-3-enyl)amine
  参考文献：
  名称：

  Catalytic Enantioselective Allylation of Ketoimines

  摘要：

  A general catalytic allylation of simple ketoimines was developed using 1 mol % of CuF(.)3PPh(3) as catalyst, 1.5 mol % of La((OPr)-Pr-/)(3) as the cocatalyst, and stable and nontoxic allylboronic acid pinacol ester as the nucleophile. This reaction constituted a good template for developing the first catalytic enantioselective allylation of ketoimines. In this case, using (LiOPr)-Pr-i as the cocatalyst produced higher enantioselectivity and reactivity than La((OPr)-Pr-i)(3). Thus, using the CuF-cyclopentyl-DuPHOS complex ( 10 mol %) and (LiOPr)-Pr-i ( 30 mol %) in the presence of tBuOH (1 equiv) produced high enantioselectivity up to 93% ee from a range of aromatic ketoimines. Mechanistic studies indicated that (LiOPr)-Pr-i accelerates the reaction by increasing the concentration of an active nucleophile, allylcopper.

  DOI：

  10.1021/ja061510h
• 作为产物：
  描述：

  2-乙酰基呋喃 、 苄胺 以 二氯甲烷 为溶剂， 生成 syn-N-<1-(furyl)ethylidene>benzylamine 、 anti-N-<1-(furyl)ethylidene>benzylamine
  参考文献：
  名称：

  N-烷基和N-芳基酮亚胺的不对称氢化反应，使用手性阳离子钌（二胺）配合物作为催化剂：抗衡阴离子和溶剂作用以及底物范围

  摘要：

  的不对称氢化ñ -烷基和Ñ通过催化芳基酮亚胺的手性阳离子η 6 -arene-（Ñ -monosulfonylated二胺）的Ru（II）络合物进行了研究。观察到强烈的抗衡阴离子和溶剂对对映选择性的影响。钌催化剂轴承非配位BARF -阴离子被认为是对无环和环外的氢化特别有效ñ -烷基酮亚胺在（BOC）的存在下2O在二氯甲烷中或什至在无溶剂条件下提供的手性胺，其ee可达99％以上，并具有完全转化率。或者，在不存在（Boc）2 O的情况下，具有手性磷酸根阴离子和相应磷酸作为添加剂的钌催化剂也有效用于N-烷基酮亚胺的氢化，对映选择性和完全转化率优异。对于Ñ -芳基酮亚胺降低通过使用钌催化剂轴承BARF观察对映体过量-阴离子。因此，该催化方案为光学活性胺提供了简便实用的途径，并已成功用于对映体纯的（+）-舍曲林的克级合成中。

  DOI：

  10.1016/j.tet.2012.03.019

文献信息

• KOBu^t/DMSO-Mediated α-C–H Vinylation of <i>N</i>-Benzyl Ketimines with Acetylene Gas: Stereoselective Synthesis of (<i>E</i>,<i>Z</i>)-2-Azadienes
  作者：Ivan A. Bidusenko、Elena Yu. Schmidt、Nadezhda I. Protsuk、Igor A. Ushakov、Alexander V. Vashchenko、Andrei V. Afonin、Boris A. Trofimov

  DOI：10.1021/acs.orglett.0c00564

  日期：2020.4.3

  Several imines, readily derived from aryl methyl ketones and benzylamines, react with acetylene gas in KOBut/DMSO system to afford 2-azadienes stereoselectively. This new C–C bond constructing reaction involves, instead of the expected ethynylation of the C═N bond, the addition of azaallyl anions to the triple bond of acetylene.

  易于衍生自芳基甲基酮和苄胺的几种亚胺在KOBu t / DMSO系统中与乙炔气体反应，以立体选择性地得到2-氮杂二烯。这种新的C–C键构建反应涉及将乙二烯丙基阴离子加到乙炔的三键上，而不是C═N键的预期乙炔化。
• Catalytic Asymmetric Hydrogenation of Imines with a Chiral Titanocene Catalyst: Scope and Limitations
  作者：Christopher A. Willoughby、Stephen L. Buchwald

  DOI：10.1021/ja00099a012

  日期：1994.10

  The asymmetric hydrogenation of imines with a chiral titanocene catalyst derived from Brintzinger's ansatitanocene complex 1 proceeds to afford amines with good to excellent enantioselectivity. The catalyst is particularly effective for the reduction of cyclic imines. For these substrates enantiomeric excesses from 95 to 99% were achieved. For acyclic imines lower enantiomeric excesses were observed. The reason for this is likely due to the fact that the acyclic imines are mixtures of anti and syn isomers which interconvert during the reaction. The catalyst was found to be tolerant of many functional groups found in organic synthesis. Thus the reaction represents an effective method for the synthesis of chiral cyclic amines.