(4R)-4-methyl-4-carboxamide-2-cinnamyl-Δ2-thiazoline | 157770-62-2

• 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: (4R)-4-methyl-4-carboxamide-2-cinnamyl-Δ2-thiazoline
• 英文别名: (4R)-4-methyl-4-carboxamide-2-cinnamyl-Δ²-thiazoline
• CAS: 157770-62-2
• 化学式: C₁₃H₁₄N₂OS
• 分子量: 246.333
• InChiKey: MVKYYMMVOSGVPX-GWJCSSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.45
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4R)-4-methyl-4-carboxamide-2-cinnamyl-Δ2-thiazoline 在 ammonium hydroxide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醇 为溶剂， 反应 50.0h， 生成 (4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ²-thiazoline)-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline
  参考文献：
  名称：

  Total synthesis of thiangazole, a novel inhibitor of HIV-1 from polyangium sp

  摘要：

  A concise total synthesis of the cinnamyl-oxazole substituted tris-thiazoline containing metabolite thiangazole 1 is described.

  DOI：

  10.1016/s0040-4039(00)77284-4
• 作为产物：
  描述：

  (4R)-4-methoxycarbonyl-4-methyl-2-cinnamyl-Δ²-thiazoline 在 氨 作用下， 以 乙醇 、 水 为溶剂， 以71%的产率得到(4R)-4-methyl-4-carboxamide-2-cinnamyl-Δ2-thiazoline
  参考文献：
  名称：

  Total synthesis of thiangazole, a novel naturally occurring HIV-1 inhibitor from Polyangium sp

  摘要：

  The total synthesis of the cinnamyl-oxazole substituted tris-thiazoline containing metabolite (-)-thiangazole (1) is described. The synthesis is based on elaboration of the R-2-methylcysteine derived bis-thiazoline nitrile (5) and oxazole (6) intermediates, followed by a cyclocondensation reaction between (5) and (6), and treatment of the resulting tris-thiazoline oxazole ester (16) with methylamine.

  DOI：

  10.1016/0040-4020(95)00356-d

文献信息

• Total synthesis of thiangazole, a novel inhibitor of HIV-1 from polyangium sp
  作者：Richard J. Boyce、Gerard C. Mulqueen、Gerald Pattenden

  DOI：10.1016/s0040-4039(00)77284-4

  日期：1994.8

  A concise total synthesis of the cinnamyl-oxazole substituted tris-thiazoline containing metabolite thiangazole 1 is described.
• Total synthesis of thiangazole, a novel naturally occurring HIV-1 inhibitor from Polyangium sp
  作者：Richard J. Boyce、Gerard C. Mulqueen、Gerald Pattenden

  DOI：10.1016/0040-4020(95)00356-d

  日期：1995.6

  The total synthesis of the cinnamyl-oxazole substituted tris-thiazoline containing metabolite (-)-thiangazole (1) is described. The synthesis is based on elaboration of the R-2-methylcysteine derived bis-thiazoline nitrile (5) and oxazole (6) intermediates, followed by a cyclocondensation reaction between (5) and (6), and treatment of the resulting tris-thiazoline oxazole ester (16) with methylamine.