(3aS,4S,4aR,6R,8aR,9aS)-4-Hydroxy-2-oxo-6-phenyl-hexahydro-3,5,7-trioxa-1-aza-cyclopenta[b]naphthalene-1-carbodithioic acid methyl ester | 187807-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3aS,4S,4aR,6R,8aR,9aS)-4-Hydroxy-2-oxo-6-phenyl-hexahydro-3,5,7-trioxa-1-aza-cyclopenta[b]naphthalene-1-carbodithioic acid methyl ester
• CAS: 187807-32-5
• 化学式: C₁₇H₁₉NO₅S₂
• 分子量: 381.474
• InChiKey: CGGIUGGNWABTCV-ULXLPNHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3aS,4S,4aR,6R,8aR,9aS)-4-Hydroxy-2-oxo-6-phenyl-hexahydro-3,5,7-trioxa-1-aza-cyclopenta[b]naphthalene-1-carbodithioic acid methyl ester 在 咪唑 、 sodium hydride 、 碘甲烷 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 6.0h， 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 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 2.0h， 生成 (3aS,4S,4aR,6R,8aR,9aS)-4-Hydroxy-2-oxo-6-phenyl-hexahydro-3,5,7-trioxa-1-aza-cyclopenta[b]naphthalene-1-carbodithioic acid methyl ester
  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