(4S)-4-methyl-4-<2'(4'R)-4'-nitrile-4'-methyl-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline | 157770-59-7

• 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: (4S)-4-methyl-4-<2'(4'R)-4'-nitrile-4'-methyl-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline
• 英文别名: (4R)-4-methyl-2-[(4S)-4-methyl-2-[(E)-2-phenylethenyl]-5H-1,3-thiazol-4-yl]-5H-1,3-thiazole-4-carbonitrile
• CAS: 157770-59-7
• 化学式: C₁₇H₁₇N₃S₂
• 分子量: 327.474
• InChiKey: ICQHITDIQDLLFZ-LJFOUZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-methyl-4-<2'(4'R)-4'-nitrile-4'-methyl-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline 在 三乙胺 、 甲胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 48.0h， 生成 (-)-Thiangazole
  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：

  (4S)-4-methyl-4-<2'(4'S)-4'-carboxamide-4'-methyl-Δ2-thiazoline>-2-cinnamyl-Δ2-thiazoline 在 三苯基膦 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 2.0h， 以15%的产率得到(4S)-4-methyl-4-<2'(4'R)-4'-nitrile-4'-methyl-Δ²-thiazoline>-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.