trans-N-allyl-N-methyl-2-tosylaminocyclohexanecarboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-N-allyl-N-methyl-2-tosylaminocyclohexanecarboxamide
• 英文别名: (1R,2R)-N-methyl-2-[(4-methylphenyl)sulfonylamino]-N-prop-2-enylcyclohexane-1-carboxamide
• 化学式: C₁₈H₂₆N₂O₃S
• 分子量: 350.482
• InChiKey: ZSWHFQFMLWYIQZ-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-N-allyl-N-methyl-2-tosylaminocyclohexanecarboxamide 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以72%的产率得到trans-N-methyl-N-((E)-prop-1-enyl)-2-tosylaminocyclohexanecarboxamide
  参考文献：
  名称：

  Solvent-Enhanced Diastereo- and Regioselectivity in the Pd^II-Catalyzed Synthesis of Six- and Eight-Membered Heterocycles viacis-Aminopalladation

  摘要：

  AbstractThe PdII‐catalyzed intramolecular oxidative cyclization of tosyl‐protected cis‐ and trans‐N‐allyl‐2‐aminocyclohexanecarboxamides was examined, and efficient syntheses of cyclohexane‐fused pyrimidin‐4‐ones and 1,5‐diazocin‐6‐ones were developed. In the course of the research, a marked solvent effect was observed on both the regio‐ and diastereoselectivity. Additionally, a novel PdII‐mediated domino oxidation, oxidative amination reaction was discovered. Our experimental and theoretical findings suggest that the reactions proceed via a cis‐aminopalladation mechanism.

  DOI：

  10.1002/chem.200900477
• 作为产物：
  描述：

  N-甲基烯丙基胺 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以4.71 g的产率得到trans-N-allyl-N-methyl-2-tosylaminocyclohexanecarboxamide
  参考文献：
  名称：

  Solvent-Enhanced Diastereo- and Regioselectivity in the Pd^II-Catalyzed Synthesis of Six- and Eight-Membered Heterocycles viacis-Aminopalladation

  摘要：

  AbstractThe PdII‐catalyzed intramolecular oxidative cyclization of tosyl‐protected cis‐ and trans‐N‐allyl‐2‐aminocyclohexanecarboxamides was examined, and efficient syntheses of cyclohexane‐fused pyrimidin‐4‐ones and 1,5‐diazocin‐6‐ones were developed. In the course of the research, a marked solvent effect was observed on both the regio‐ and diastereoselectivity. Additionally, a novel PdII‐mediated domino oxidation, oxidative amination reaction was discovered. Our experimental and theoretical findings suggest that the reactions proceed via a cis‐aminopalladation mechanism.

  DOI：

  10.1002/chem.200900477

文献信息

• Solvent-Enhanced Diastereo- and Regioselectivity in the Pd^II-Catalyzed Synthesis of Six- and Eight-Membered Heterocycles via<i>cis</i>-Aminopalladation
  作者：Árpád Balázs、Anasztázia Hetényi、Zsolt Szakonyi、Reijo Sillanpää、Ferenc Fülöp

  DOI：10.1002/chem.200900477

  日期：2009.7.27

  AbstractThe PdII‐catalyzed intramolecular oxidative cyclization of tosyl‐protected cis‐ and trans‐N‐allyl‐2‐aminocyclohexanecarboxamides was examined, and efficient syntheses of cyclohexane‐fused pyrimidin‐4‐ones and 1,5‐diazocin‐6‐ones were developed. In the course of the research, a marked solvent effect was observed on both the regio‐ and diastereoselectivity. Additionally, a novel PdII‐mediated domino oxidation, oxidative amination reaction was discovered. Our experimental and theoretical findings suggest that the reactions proceed via a cis‐aminopalladation mechanism.