1H-Imidazole-1-carbothioic acid,O-[(2R,4S,5R)-4-[(dimethylhydrazono)methyl]-2-phenyl-1,3-dioxan-5-yl]ester | 501373-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 1H-Imidazole-1-carbothioic acid,O-[(2R,4S,5R)-4-[(dimethylhydrazono)methyl]-2-phenyl-1,3-dioxan-5-yl]ester
• 英文别名: imidazole-1-carbothioic acid O-[4-(S)-(dimethyl-hydrazonomethyl)-2-(R)-phenyl-[1,3]dioxan-5-(R)-yl] ester
• CAS: 501373-27-9
• 化学式: C₁₇H₂₀N₄O₃S
• 分子量: 360.437
• InChiKey: XCUXCVBTPRFJSP-ARFHVFGLSA-N

物化性质

• 沸点：
  528.5±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  61.11
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1H-Imidazole-1-carbothioic acid,O-[(2R,4S,5R)-4-[(dimethylhydrazono)methyl]-2-phenyl-1,3-dioxan-5-yl]ester 在 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 苯 为溶剂， 反应 5.0h， 以54%的产率得到N'-((2R,4aR,6S,7S,7aS)-6-Imidazol-1-yl-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl)-N,N-dimethyl-hydrazine
  参考文献：
  名称：

  A New Reaction Manifold for the Barton Radical Intermediates:  Synthesis of N-Heterocyclic Furanosides and Pyranosides via the Formation of the C₁−C₂ Bond

  摘要：

  The first radical intermediate in the thiourethane-mediated deoxygenation of an alcohol (Barton-McCombie reaction) can participate in an exo-hex-5-enyl- or exo-hept-6-enyl-type radical cyclization when a suitable radical acceptor (e.g., alpha,beta-unsaturated ester, oxime ether, or hydrazone) is appropriately placed. Carbohydrate-derived imidazolyl and triazolyl thiourethanes with such acceptors, upon addition to excess of a good hydride donor (reverse addition), undergo efficient cyclization reactions to give N-heterocyclic furanosides, and, surprisingly even N-pyranosides. Depending on the acceptor, glycosides with either a C(2)()-amino or a C(2)()-carbon substituent are formed.

  DOI：

  10.1021/ja028617z
• 作为产物：
  描述：

  2,4-O-苄叉-D-赤藓糖 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.5h， 生成 1H-Imidazole-1-carbothioic acid,O-[(2R,4S,5R)-4-[(dimethylhydrazono)methyl]-2-phenyl-1,3-dioxan-5-yl]ester
  参考文献：
  名称：

  A New Reaction Manifold for the Barton Radical Intermediates:  Synthesis of N-Heterocyclic Furanosides and Pyranosides via the Formation of the C₁−C₂ Bond

  摘要：

  The first radical intermediate in the thiourethane-mediated deoxygenation of an alcohol (Barton-McCombie reaction) can participate in an exo-hex-5-enyl- or exo-hept-6-enyl-type radical cyclization when a suitable radical acceptor (e.g., alpha,beta-unsaturated ester, oxime ether, or hydrazone) is appropriately placed. Carbohydrate-derived imidazolyl and triazolyl thiourethanes with such acceptors, upon addition to excess of a good hydride donor (reverse addition), undergo efficient cyclization reactions to give N-heterocyclic furanosides, and, surprisingly even N-pyranosides. Depending on the acceptor, glycosides with either a C(2)()-amino or a C(2)()-carbon substituent are formed.

  DOI：

  10.1021/ja028617z