(3aS,4S,4aR,6R,8aR,9aS)-4-Hydroxy-6-phenyl-hexahydro-3,5,7-trioxa-1-aza-cyclopenta[b]naphthalen-2-one | 187807-30-3

• 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: (3aS,4S,4aR,6R,8aR,9aS)-4-Hydroxy-6-phenyl-hexahydro-3,5,7-trioxa-1-aza-cyclopenta[b]naphthalen-2-one
• 英文别名: (1R,3S,7S,8S,9R,11R)-8-hydroxy-11-phenyl-6,10,12-trioxa-4-azatricyclo[7.4.0.03,7]tridecan-5-one
• CAS: 187807-30-3
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: RYDBDQYLAGHWHM-GUDWOMEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4S,4aR,6R,8aR,9aS)-4-Hydroxy-6-phenyl-hexahydro-3,5,7-trioxa-1-aza-cyclopenta[b]naphthalen-2-one 在 咪唑 、 sodium hydride 、 碘甲烷 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 3.0h， 生成 (1R,2S,6R,7S,9R,12R)-7-[bis(methylsulfanyl)methylideneamino]-12-phenyl-3,11,13-trioxa-5-thiatricyclo[7.4.0.02,6]tridecane-4-thione
  参考文献：
  名称：

  Thiovalidamine Derivatives of manno-and gluco-Type: Remote Activation and Anchimeric Assistance

  摘要：

  The oxazolidone (3) derived from validamine (1) was dithiocarbonylated, on treatment with NaH followed by CS2-MeI, to the N,O-dicarbodithioate (6). On treatment with NaH-MeI, this afforded the manno-type thiovalidamine derivative (7) and then the gluco-type thiovalidamine derivative (8) following the pathway shown in Scheme 2: an activation at a C=S group by methylation, transferring this activation to a remote position accompanied with decarboxylation, and cyclization of the neighboring group to the transferred position (C-3).

  DOI：

  10.3987/com-96-s41
• 作为产物：
  描述：

  1,7-O-benzylidene-N-carbobenzyloxy validamine 在 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 1.0h， 以87%的产率得到(3aS,4S,4aR,6R,8aR,9aS)-4-Hydroxy-6-phenyl-hexahydro-3,5,7-trioxa-1-aza-cyclopenta[b]naphthalen-2-one
  参考文献：
  名称：

  Thiovalidamine Derivatives of manno-and gluco-Type: Remote Activation and Anchimeric Assistance

  摘要：

  The oxazolidone (3) derived from validamine (1) was dithiocarbonylated, on treatment with NaH followed by CS2-MeI, to the N,O-dicarbodithioate (6). On treatment with NaH-MeI, this afforded the manno-type thiovalidamine derivative (7) and then the gluco-type thiovalidamine derivative (8) following the pathway shown in Scheme 2: an activation at a C=S group by methylation, transferring this activation to a remote position accompanied with decarboxylation, and cyclization of the neighboring group to the transferred position (C-3).

  DOI：

  10.3987/com-96-s41