(2R,5S)-trimethylsilyl 5-methylpiperidine-2-carboxylate | 1430078-13-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,5S)-trimethylsilyl 5-methylpiperidine-2-carboxylate
• 英文别名: trimethylsilyl (2R,5S)-5-methylpiperidine-2-carboxylate
• CAS: 1430078-13-9
• 化学式: C₁₀H₂₁NO₂Si
• 分子量: 215.368
• InChiKey: DRYDZKJJPHDLML-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5S)-trimethylsilyl 5-methylpiperidine-2-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 、 甲苯 、 萘烷 为溶剂， 120.0 ℃ 、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：

  rac-(2S,5R)-1-tert-butoxycarbonyl-5-methylpiperidine-2-carboxylic acid 在 poly-4-vinylpyridine 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 (2R,5S)-trimethylsilyl 5-methylpiperidine-2-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.