benzyl 2-(N-allyl-2,2,2-trifluoroacetamido)ethylcarbamate | 1007121-66-5

• 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: benzyl 2-(N-allyl-2,2,2-trifluoroacetamido)ethylcarbamate
• 英文别名: benzyl N-[2-[prop-2-enyl-(2,2,2-trifluoroacetyl)amino]ethyl]carbamate
• CAS: 1007121-66-5
• 化学式: C₁₅H₁₇F₃N₂O₃
• 分子量: 330.307
• InChiKey: NYDJNSUONWZVMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-(N-allyl-2,2,2-trifluoroacetamido)ethylcarbamate 在 (2,6-bis(diphenylphosphinomethyl)pyridine)dichloropalladium 四氟硼酸-二乙醚络合物 、 silver tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以99%的产率得到benzyl 4-(2,2,2-trifluoroacetyl)-2-methylpiperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction

  摘要：

  A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A(1,3) strain.

  DOI：

  10.1021/ol702891p
• 作为产物：
  描述：

  N-allyl-N'-carbobenzoxyethylenediamine 、 三氟乙酸酐 以 二氯甲烷 为溶剂， 反应 20.0h， 以69%的产率得到benzyl 2-(N-allyl-2,2,2-trifluoroacetamido)ethylcarbamate
  参考文献：
  名称：

  Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction

  摘要：

  A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A(1,3) strain.

  DOI：

  10.1021/ol702891p

文献信息

• Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction
  作者：Brian M. Cochran、Forrest E. Michael

  DOI：10.1021/ol702891p

  日期：2008.1.1

  A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A(1,3) strain.