(R)-N¹-allyl-N¹-benzyl-3-(benzyloxy)propane-1,2-diamine | 950608-97-6

• 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: (R)-N¹-allyl-N¹-benzyl-3-(benzyloxy)propane-1,2-diamine
• 英文别名: (R)-N1-allyl-N1-benzyl-3-benzyloxypropane-1,2-diamine；(2R)-1-N-benzyl-3-phenylmethoxy-1-N-prop-2-enylpropane-1,2-diamine
• CAS: 950608-97-6
• 化学式: C₂₀H₂₆N₂O
• 分子量: 310.439
• InChiKey: QAWPWALLAHGKKY-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N¹-allyl-N¹-benzyl-3-(benzyloxy)propane-1,2-diamine 在 tris(dibenzylideneacetone)dipalladium (0) 三(2-呋喃基)膦 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 (+)-(2R,6R)-4-[4-benzyl-2-benzyloxymethyl-6-(4-trifluoromethylbenzyl)piperazin-1-yl]benzonitrile
  参考文献：
  名称：

  A Concise Asymmetric Synthesis of cis-2,6-Disubstituted N-Aryl Piperazines via Pd-Catalyzed Carboamination Reactions

  摘要：

  A concise, modular, asymmetric synthesis of cis-2,6-disubstituted piperazines from readily available amino acid precursors is described. The key step in the synthesis is a Pd-catalyzed carboamination of a N-1-aryl-N-2-allyl-1,2-diamine with an aryl bromide. The products are obtained in 14-20:1 dr, with > 97% ee, and the key cyclizations are the first examples of six-membered ring formation via Pd-catalyzed carboamination reactions of unsaturated amines with aryl halides.

  DOI：

  10.1021/ol071241f
• 作为产物：
  描述：

  N-烯丙基苄胺 在 盐酸 、 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (R)-N¹-allyl-N¹-benzyl-3-(benzyloxy)propane-1,2-diamine
  参考文献：
  名称：

  A Concise Asymmetric Synthesis of cis-2,6-Disubstituted N-Aryl Piperazines via Pd-Catalyzed Carboamination Reactions

  摘要：

  A concise, modular, asymmetric synthesis of cis-2,6-disubstituted piperazines from readily available amino acid precursors is described. The key step in the synthesis is a Pd-catalyzed carboamination of a N-1-aryl-N-2-allyl-1,2-diamine with an aryl bromide. The products are obtained in 14-20:1 dr, with > 97% ee, and the key cyclizations are the first examples of six-membered ring formation via Pd-catalyzed carboamination reactions of unsaturated amines with aryl halides.

  DOI：

  10.1021/ol071241f

文献信息

• Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines
  作者：Josephine S. Nakhla、Danielle M. Schultz、John P. Wolfe

  DOI：10.1016/j.tet.2009.04.017

  日期：2009.8

  piperazines from amino acid precursors is described. The target compounds are generated in 95–99% ee with good to excellent levels of diastereoselectivity (usually 14:1 to >20:1) using Pd-catalyzed carboamination reactions between aryl or alkenyl halides and substituted ethylenediamine derivatives to form the heterocyclic rings. The synthesis requires only 4–5 steps from commercially available amino acids, and

  描述了从氨基酸前体立体选择性制备对映体富集的顺式-2,6-二取代哌嗪的策略。使用 Pd 催化芳基或烯基卤化物与取代乙二胺衍生物之间的碳胺化反应形成杂环，以 95-99% ee 生成目标化合物，具有良好至极好的非对映选择性（通常为 14:1 至 >20:1）。合成仅需 4-5 步即可从市售氨基酸中提取，并允许模块化构建在 N 1、N 4、C 2和 C 6处具有不同取代基的哌嗪. 还报道了使用这种策略构建 2,3-二取代哌嗪、稠合双环哌嗪和四氢喹喔啉。此外，讨论了关键的碳胺化反应的机理，并提出了预测和解释这些转化立体化学结果的新模型。
• A Concise Asymmetric Synthesis of <i>cis</i>-2,6-Disubstituted <i>N</i>-Aryl Piperazines via Pd-Catalyzed Carboamination Reactions
  作者：Josephine S. Nakhla、John P. Wolfe

  DOI：10.1021/ol071241f

  日期：2007.8.1

  A concise, modular, asymmetric synthesis of cis-2,6-disubstituted piperazines from readily available amino acid precursors is described. The key step in the synthesis is a Pd-catalyzed carboamination of a N-1-aryl-N-2-allyl-1,2-diamine with an aryl bromide. The products are obtained in 14-20:1 dr, with > 97% ee, and the key cyclizations are the first examples of six-membered ring formation via Pd-catalyzed carboamination reactions of unsaturated amines with aryl halides.