10-[(2,2-dimethyl-4H-1,3-benzodioxin-4-yl)methyl]-3-methyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene | 606977-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 10-[(2,2-dimethyl-4H-1,3-benzodioxin-4-yl)methyl]-3-methyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene
• CAS: 606977-34-8
• 化学式: C₂₃H₂₆N₂O₂
• 分子量: 362.472
• InChiKey: YYCWSEFWMLDMRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  26.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-[(2,2-dimethyl-4H-1,3-benzodioxin-4-yl)methyl]-3-methyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene 以 萘烷 为溶剂， 反应 27.0h， 以59%的产率得到(3R,11S,19S)-12-methyl-10-oxa-1,12-diazahexacyclo[15.4.1.03,19.04,9.011,19.013,18]docosa-4,6,8,13,15,17-hexaene
  参考文献：
  名称：

  A Synthetic Approach to Nomofungin/Communesin B

  摘要：

  [GRAPHICS]A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an orthoquinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.

  DOI：

  10.1021/ol034407v
• 作为产物：
  描述：

  ethyl hydroxy(2-hydroxyphenyl)acetate 在 氢氧化钾 、 lithium aluminium tetrahydride 、 草酰氯 、 camphor-10-sulfonic acid 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.16h， 生成 10-[(2,2-dimethyl-4H-1,3-benzodioxin-4-yl)methyl]-3-methyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene
  参考文献：
  名称：

  A Synthetic Approach to Nomofungin/Communesin B

  摘要：

  [GRAPHICS]A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an orthoquinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.

  DOI：

  10.1021/ol034407v

文献信息

• A Synthetic Approach to Nomofungin/Communesin B
  作者：Seth L. Crawley、Raymond L. Funk

  DOI：10.1021/ol034407v

  日期：2003.9.1

  [GRAPHICS]A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an orthoquinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.