(S)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate | 1242597-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate
• 英文别名: [(8aS)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-7-yl] trifluoromethanesulfonate
• CAS: 1242597-71-2
• 化学式: C₁₆H₁₈F₃NO₄S
• 分子量: 377.384
• InChiKey: YZQMGAPIBAFMEP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-溴黎芦醚 、 (S)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate 在 叔丁基锂 、 zinc dibromide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 2.0h， 以96%的产率得到(+)-seco-antofine
  参考文献：
  名称：

  Total Syntheses of Arylindolizidine Alkaloids (+)-Ipalbidine and (+)-Antofine

  摘要：

  This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C-H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24-26% overall yields.

  DOI：

  10.1021/jo101051w
• 作为产物：
  描述：

  1-aza-3-(4-methoxyphenyl)bicyclo<4,3,0>nonan-4-one 、 2-[N,正双(三氟甲烷烷磺酰)氨基]-5-氯吡啶 以 四氢呋喃 为溶剂， 反应 2.0h， 以690 mg的产率得到(S)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Total Syntheses of Arylindolizidine Alkaloids (+)-Ipalbidine and (+)-Antofine

  摘要：

  This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C-H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24-26% overall yields.

  DOI：

  10.1021/jo101051w

文献信息

• Total Syntheses of Arylindolizidine Alkaloids (+)-Ipalbidine and (+)-Antofine
  作者：Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/jo101051w

  日期：2010.9.3

  This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C-H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24-26% overall yields.