N1,N2-bis(tert-butyloxycarbonyl)-N1-(1-naphth-1-yl-prop-2-enyl)guanidine | 1092657-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N1,N2-bis(tert-butyloxycarbonyl)-N1-(1-naphth-1-yl-prop-2-enyl)guanidine
• 英文别名: tert-butyl N-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-[(1S)-1-naphthalen-1-ylprop-2-enyl]carbamate
• CAS: 1092657-92-5
• 化学式: C₂₄H₃₁N₃O₄
• 分子量: 425.528
• InChiKey: YVBZBQURQYLTSB-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Diethyl 3-(naphthalen-1-yl)prop-2-en-1-yl phosphate 、 1,3-二(叔丁氧基羰基)胍 在 氢氧化铯 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 2,6-二[(4S)-4-苯基-2-恶唑啉基]吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.17h， 以69%的产率得到N1,N2-bis(tert-butyloxycarbonyl)-N1-(1-naphth-1-yl-prop-2-enyl)guanidine
  参考文献：
  名称：

  Palladium- or Iridium-Catalyzed Allylic Substitution of Guanidines: Convenient and Direct Modification of Guanidines

  摘要：

  As a convenient and direct functionalization of guanidines, the transition metal-catalyzed allylic substitution of guanidines was studied. The guanidine derivatives bearing two electron-withdrawing substituents acted as reactive nucleophiles in the allylic substitution to give the rnonoallylated products. The double allylic substitution was achieved by using tri-Boc-guanidine bearing three electron-withdrawing substituents as a nucleophile to give the diallylated products. The regiocontrol in the allylic substitution of unsymmetrical allylic substrates has been investigated by employing the palladium or iridium catalysts. The iridium complex of chiral pybox ligand allowed the regio- and enantioselective allylic substitution. Asymmetric double allylic substitution of tri-Boc-guanidine with phosphate bearing the 1-naphthyl group gave the diallylated product with high diastereo-, regio-, and enantioselectivities.

  DOI：

  10.1021/jo802271d

文献信息

• Palladium- or Iridium-Catalyzed Allylic Substitution of Guanidines: Convenient and Direct Modification of Guanidines
  作者：Hideto Miyabe、Kazumasa Yoshida、Valluru Krishna Reddy、Yoshiji Takemoto

  DOI：10.1021/jo802271d

  日期：2009.1.2

  As a convenient and direct functionalization of guanidines, the transition metal-catalyzed allylic substitution of guanidines was studied. The guanidine derivatives bearing two electron-withdrawing substituents acted as reactive nucleophiles in the allylic substitution to give the rnonoallylated products. The double allylic substitution was achieved by using tri-Boc-guanidine bearing three electron-withdrawing substituents as a nucleophile to give the diallylated products. The regiocontrol in the allylic substitution of unsymmetrical allylic substrates has been investigated by employing the palladium or iridium catalysts. The iridium complex of chiral pybox ligand allowed the regio- and enantioselective allylic substitution. Asymmetric double allylic substitution of tri-Boc-guanidine with phosphate bearing the 1-naphthyl group gave the diallylated product with high diastereo-, regio-, and enantioselectivities.