methyl (1S,3R,6S,7S,8S,9S)-6-[(4-methoxyphenyl)methyl]-7,9-bis(phenylmethoxy)-5-azatricyclo[6.3.1.01,5]dodecane-3-carboxylate | 1111780-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl (1S,3R,6S,7S,8S,9S)-6-[(4-methoxyphenyl)methyl]-7,9-bis(phenylmethoxy)-5-azatricyclo[6.3.1.01,5]dodecane-3-carboxylate
• CAS: 1111780-21-2
• 化学式: C₃₅H₄₁NO₅
• 分子量: 555.714
• InChiKey: FQEKWQYNGPJRTR-JIIJLPCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1S,3R,6S,7S,8S,9S)-6-[(4-methoxyphenyl)methyl]-7,9-bis(phenylmethoxy)-5-azatricyclo[6.3.1.01,5]dodecane-3-carboxylate 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 生成 methyl (1S,3S,6S,7S,8S,9S)-6-[(4-methoxyphenyl)methyl]-7,9-bis(phenylmethoxy)-5-azatricyclo[6.3.1.01,5]dodecane-3-carboxylate
  参考文献：
  名称：

  Total Synthesis of FR901483

  摘要：

  The architecturally sophisticated skeleton of the immunosuppressive alkaloid FR901483 was assembled via a process relying on the reaction of an in situ generated imine with a suitably disposed donor-acceptor cyclopropane. A short sequence of functional group transformations provided the natural product in an efficient manner.

  DOI：

  10.1021/ol802870c
• 作为产物：
  描述：

  dimethyl (1S,6S,7S,8S,9S)-6-[(4-methoxyphenyl)methyl]-7,9-bis(phenylmethoxy)-5-azatricyclo[6.3.1.01,5]dodecane-3,3-dicarboxylate 在 sodium cyanide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.67h， 以23 mg的产率得到methyl (1S,3S,6S,7S,8S,9S)-6-[(4-methoxyphenyl)methyl]-7,9-bis(phenylmethoxy)-5-azatricyclo[6.3.1.01,5]dodecane-3-carboxylate
  参考文献：
  名称：

  Total Synthesis of FR901483

  摘要：

  The architecturally sophisticated skeleton of the immunosuppressive alkaloid FR901483 was assembled via a process relying on the reaction of an in situ generated imine with a suitably disposed donor-acceptor cyclopropane. A short sequence of functional group transformations provided the natural product in an efficient manner.

  DOI：

  10.1021/ol802870c

文献信息

• Total Synthesis of FR901483
  作者：Cheryl A. Carson、Michael A. Kerr

  DOI：10.1021/ol802870c

  日期：2009.2.5

  The architecturally sophisticated skeleton of the immunosuppressive alkaloid FR901483 was assembled via a process relying on the reaction of an in situ generated imine with a suitably disposed donor-acceptor cyclopropane. A short sequence of functional group transformations provided the natural product in an efficient manner.