(4S,5S)-4,5-diazidocyclohex-1-ene | 1448438-53-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (4S,5S)-4,5-diazidocyclohex-1-ene
• 英文别名: (4S,5S)-4,5-diazidocyclohexene
• CAS: 1448438-53-6
• 化学式: C₆H₈N₆
• 分子量: 164.17
• InChiKey: KPRARVDAEPLFFF-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4,5-diazidocyclohex-1-ene 在 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 (1S,2S)-N,N'-di(tert-butoxycarbonyl)cyclohex-4-ene-1,2-diamine
  参考文献：
  名称：

  Enhanced Rate and Selectivity by Carboxylate Salt as a Basic Cocatalyst in Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric Acylation of Secondary Alcohols

  摘要：

  The rate and enantioselectivity of chiral NHC-catalyzed asymmetric acylation of alcohols with an adjacent H-bond donor functionality are remarkably enhanced in the presence of a carboxylate cocatalyst. The degree of the enhancement is correlated with the basicity of the carboxylate. With a cocatalyst and a newly developed electron-deficient chiral NHC, kinetic resolution and desymmetrization of cyclic diols and amino alcohols were achieved with extremely high selectivity (up to s = 218 and 99% ee, respectively) at a low catalyst loading (0.5 mol %). This asymmetric acylation is characterized by a unique preference for alcohols over amines, which are not converted into amides under the reaction conditions.

  DOI：

  10.1021/ja4055838
• 作为产物：
  描述：

  环己-4-烯-1,2-二醇 在 吡啶 、 sodium azide 、 三氟甲磺酸酐 、 (5aS,10bR)-9-nitro-2-phenyl-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate 、 4-二甲氨基苯甲酸 、 1,8-双二甲氨基萘 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.17h， 生成 (4S,5S)-4,5-diazidocyclohex-1-ene
  参考文献：
  名称：

  Enhanced Rate and Selectivity by Carboxylate Salt as a Basic Cocatalyst in Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric Acylation of Secondary Alcohols

  摘要：

  The rate and enantioselectivity of chiral NHC-catalyzed asymmetric acylation of alcohols with an adjacent H-bond donor functionality are remarkably enhanced in the presence of a carboxylate cocatalyst. The degree of the enhancement is correlated with the basicity of the carboxylate. With a cocatalyst and a newly developed electron-deficient chiral NHC, kinetic resolution and desymmetrization of cyclic diols and amino alcohols were achieved with extremely high selectivity (up to s = 218 and 99% ee, respectively) at a low catalyst loading (0.5 mol %). This asymmetric acylation is characterized by a unique preference for alcohols over amines, which are not converted into amides under the reaction conditions.

  DOI：

  10.1021/ja4055838

文献信息

• Enhanced Rate and Selectivity by Carboxylate Salt as a Basic Cocatalyst in Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric Acylation of Secondary Alcohols
  作者：Satoru Kuwano、Shingo Harada、Bubwoong Kang、Raphaël Oriez、Yousuke Yamaoka、Kiyosei Takasu、Ken-ichi Yamada

  DOI：10.1021/ja4055838

  日期：2013.8.7

  The rate and enantioselectivity of chiral NHC-catalyzed asymmetric acylation of alcohols with an adjacent H-bond donor functionality are remarkably enhanced in the presence of a carboxylate cocatalyst. The degree of the enhancement is correlated with the basicity of the carboxylate. With a cocatalyst and a newly developed electron-deficient chiral NHC, kinetic resolution and desymmetrization of cyclic diols and amino alcohols were achieved with extremely high selectivity (up to s = 218 and 99% ee, respectively) at a low catalyst loading (0.5 mol %). This asymmetric acylation is characterized by a unique preference for alcohols over amines, which are not converted into amides under the reaction conditions.