(6S,8aR)-7-[(dimethylamino)methylene]tetrahydro-6-[(1R)-3-hydroxy-1-[(2-methoxyethoxy)methoxy]-2-(phenylseleno)propyl]-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8-trione | 1096711-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (6S,8aR)-7-[(dimethylamino)methylene]tetrahydro-6-[(1R)-3-hydroxy-1-[(2-methoxyethoxy)methoxy]-2-(phenylseleno)propyl]-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8-trione
• CAS: 1096711-57-7
• 化学式: C₂₉H₄₅N₃O₇SSeSi
• 分子量: 686.804
• InChiKey: SETGJFMWGPNZGD-QTONPECPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  42.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  108.85
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (6S,8aR)-7-[(dimethylamino)methylene]tetrahydro-6-[(1R)-3-hydroxy-1-[(2-methoxyethoxy)methoxy]-2-(phenylseleno)propyl]-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8-trione 在 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 50.0h， 以77%的产率得到(5aS,6R,11aR)-2,3,5a,6,7,8-hexahydro-6-[(2-methoxyethoxy)methoxy]-2-methyl-7-(phenylseleno)-11a-[[2-(trimethylsilyl)ethyl]thio]oxepino[3',4':4,5]pyrrolo[1,2-a]pyrazine-1,4,11(11aH)-trione
  参考文献：
  名称：

  Asymmetric Synthesis of the ABC-Ring System of the Antitumor Antibiotic MPC1001

  摘要：

  trans-4-Hydroxy-L-proline was converted into a tricyclic compound representing three contiguous rings of the anticancer antibiotic MPC1001. The tricyclic model contains the dihydrooxepin and diketopiperazine Subunits, as well as one of the Sulfur atoms of the natural product. The diketopiperazine unit was formed by a new method that involves cyclization of an enolate onto the carbonyl of a phenyl carbamate, and the dihydrooxepin ring was generated by using an acid-induced cyclization of an alcohol onto the beta-carbon of a vinylogous amide.

  DOI：

  10.1021/jo802344t
• 作为产物：
  描述：

  (6S,8aR)-tetrahydro-6-[(1R)-3-hydroxy-1-[(2-methoxyethoxy)methoxy]-2-(phenylseleno)propyl]-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8-trione 、 N,N-二甲基甲酰胺二甲基缩醛 以 四氢呋喃 为溶剂， 反应 44.0h， 以70%的产率得到(6S,8aR)-7-[(dimethylamino)methylene]tetrahydro-6-[(1R)-3-hydroxy-1-[(2-methoxyethoxy)methoxy]-2-(phenylseleno)propyl]-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8-trione
  参考文献：
  名称：

  Asymmetric Synthesis of the ABC-Ring System of the Antitumor Antibiotic MPC1001

  摘要：

  trans-4-Hydroxy-L-proline was converted into a tricyclic compound representing three contiguous rings of the anticancer antibiotic MPC1001. The tricyclic model contains the dihydrooxepin and diketopiperazine Subunits, as well as one of the Sulfur atoms of the natural product. The diketopiperazine unit was formed by a new method that involves cyclization of an enolate onto the carbonyl of a phenyl carbamate, and the dihydrooxepin ring was generated by using an acid-induced cyclization of an alcohol onto the beta-carbon of a vinylogous amide.

  DOI：

  10.1021/jo802344t