N-Benzyl-2-ethylbutan-1-imine N-oxide | 1165676-27-6

• 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-2-ethylbutan-1-imine N-oxide
• 英文别名: N-benzyl-2-ethylbutan-1-imine oxide
• CAS: 1165676-27-6
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: MXQNRHCAQYQRQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Benzyl-2-ethylbutan-1-imine N-oxide 、 苯乙炔 在 indium(III) bromide 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到
  参考文献：
  名称：

  InBr3-catalyzed direct alkynylation of nitrones with terminal alkynes: an efficient synthesis of N-hydroxy-propargyl amines

  摘要：

  An InBr3-Catalyzed direct and efficient alkynylation of nitrones with terminal alkynes was developed. The process enables practical synthesis of a wide range of synthetically useful N-hydroxy-propargyl amine derivatives in good yields under mild conditions. The application of this method to optically active propargylic N-hydroxyamines syntheses was also described. With chiral nitrones, good diastereoselectivities were obtained. Moreover, the first chiral indium(III) complex-catalyzed asymmetric alkynylation of nitrone was achieved with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.206

文献信息

• Catalytic Enantioselective Alkyne Addition to Nitrones Enabled by Tunable Axially Chiral Imidazole-Based P,N-Ligands
  作者：Shengkang Yin、Kendall N. Weeks、Aaron Aponick

  DOI：10.1021/jacs.4c00873

  日期：2024.3.20

  reaction accommodates a wide range of nitrones and alkynes, enabling the streamlined synthesis of chiral propargyl N-hydroxylamines via the enantioselective C–C bond formation. A diverse array of optically active nitrogen-containing compounds, including chiral hydroxylamines, can be accessed directly through facile transformations of the reaction products.

  尽管催化对映选择性炔烃加成是合成手性炔丙醇和胺的既定方法，但硝酮的加成提出了独特的挑战，并且尚未开发出通用的手性催化剂体系。在这篇手稿中，我们报道了利用可调节的轴向手性咪唑基P 、 N配体，首次将铜催化的对映选择性炔烃加成到硝酮上。我们的方法有效地克服了反应性和选择性方面的困难，从而产生了简单的铜催化方案。该反应适用于多种硝酮和炔烃，能够通过对映选择性 C-C 键形成来简化手性炔丙基N-羟胺的合成。通过反应产物的简单转化，可以直接获得多种光学活性含氮化合物，包括手性羟胺。
• 10.1021/acscatal.4c03508
  作者：Zhao, Zhen-Ni、He, Feng-Kai、Wang, Yu-Hao、Li, Yi-Chao、Li, Zi-Han、Yang, Xiao-Yu、Schneider, Uwe、Huang, Yi-Yong

  DOI：10.1021/acscatal.4c03508

  日期：——

  The enantioselective 1,3-dipolar cycloaddition of alkynes and α-aliphatic nitrones has long been recognized as an important challenge, while considerable progress has been made for the alkenes and aromatic nitrones. We herein report an example of an earth-abundant iron-catalyzed enantioselective click-approach 1,3-dipolar cycloaddition of nonterminal alkynyl imides and α-aliphatic nitrones, and highly

  炔烃和α-脂肪族硝酮的对映选择性1,3-偶极环加成长期以来被认为是一个重要的挑战，而烯烃和芳香硝酮的对映选择性1,3-偶极环加成反应已经取得了相当大的进展。我们在此报道了非末端炔基酰亚胺和α-脂肪族硝酮以及具有3-烷基取代的立体碳中心的高度官能化的手性4-异恶唑啉的地球丰富的铁催化对映选择性点击法1,3-偶极环加成的例子模块化生成，产率高达 >99%， ee高达 98%（54 个示例）。尽管硝酮上的空间取代基在实现有效的对映控制中起着关键作用，但硝酮的直链烷基链（Me、Et等）和H之间的空间偏向差异的挑战也被成功克服。对映体歧视可能源于含有双三齿配体 (L*·Fe(OTf) 2 ·L*, L* = ( R , R )-DBFOX-Ph ）的明确八面体单核亚铁络合物和可能的双模式σ,π 结合激活，ESI-HRMS 和单晶 X 射线分析以及 L*/Fe 比率效应和 DFT 计算证明了这一点。可
• InBr3-catalyzed direct alkynylation of nitrones with terminal alkynes: an efficient synthesis of N-hydroxy-propargyl amines
  作者：Du-Ming Ji、Ming-Hua Xu

  DOI：10.1016/j.tetlet.2009.03.206

  日期：2009.6

  An InBr3-Catalyzed direct and efficient alkynylation of nitrones with terminal alkynes was developed. The process enables practical synthesis of a wide range of synthetically useful N-hydroxy-propargyl amine derivatives in good yields under mild conditions. The application of this method to optically active propargylic N-hydroxyamines syntheses was also described. With chiral nitrones, good diastereoselectivities were obtained. Moreover, the first chiral indium(III) complex-catalyzed asymmetric alkynylation of nitrone was achieved with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.