ethyl (1S,2R,5S,7S,10S,11S,14S,17R,20S,23R)-7-[tert-butyl(diphenyl)silyl]oxy-10,14,20-trimethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-15-ene-16-carboxylate | 1430078-16-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: ethyl (1S,2R,5S,7S,10S,11S,14S,17R,20S,23R)-7-[tert-butyl(diphenyl)silyl]oxy-10,14,20-trimethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-15-ene-16-carboxylate
• CAS: 1430078-16-2
• 化学式: C₄₅H₆₃NO₃Si
• 分子量: 694.086
• InChiKey: XDEACCOHZDPEMH-GZTNCFLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.93
• 重原子数：
  50
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1S,2R,5S,7S,10S,11S,14S,17R,20S,23R)-7-[tert-butyl(diphenyl)silyl]oxy-10,14,20-trimethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-15-ene-16-carboxylate 在 platinum(IV) oxide 、 lithium aluminium tetrahydride 、 platinum 、 四丁基氟化铵 、 氢气 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 萘烷 为溶剂， 70.0 ℃ 、4.14 MPa 条件下， 反应 67.0h， 生成 垂茄次碱
  参考文献：
  名称：

  Synthesis of Demissidine by a Ring Fragmentation 1,3-Dipolar Cycloaddition Approach

  摘要：

  A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.

  DOI：

  10.1021/ol4004993
• 作为产物：
  描述：

  表雄酮 在 咪唑 、 4-二甲氨基吡啶 、 水 、 四氯化锡 、 sodium hydroxide 、 copper(ll) bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.75h， 生成 ethyl (1S,2R,5S,7S,10S,11S,14S,17R,20S,23R)-7-[tert-butyl(diphenyl)silyl]oxy-10,14,20-trimethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-15-ene-16-carboxylate
  参考文献：
  名称：

  Synthesis of Demissidine by a Ring Fragmentation 1,3-Dipolar Cycloaddition Approach

  摘要：

  A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.

  DOI：

  10.1021/ol4004993

文献信息

• Synthesis of Demissidine by a Ring Fragmentation 1,3-Dipolar Cycloaddition Approach
  作者：Zhe Zhang、Geoffrey M. Giampa、Cristian Draghici、Qiufeng Huang、Matthias Brewer

  DOI：10.1021/ol4004993

  日期：2013.5.3

  A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.