(1R,2R,6R,7S,8aR)-1,2-dihydroxy-6,7-(isopropylidene)dioxy-3-oxo-indolizidine | 334022-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1R,2R,6R,7S,8aR)-1,2-dihydroxy-6,7-(isopropylidene)dioxy-3-oxo-indolizidine
• 英文别名: Bbakpuforqonar-anzwqobjsa-；(3aR,7R,8R,8aR,9aS)-7,8-dihydroxy-2,2-dimethyl-4,7,8,8a,9,9a-hexahydro-3aH-[1,3]dioxolo[4,5-f]indolizin-6-one
• CAS: 334022-71-8
• 化学式: C₁₁H₁₇NO₅
• 分子量: 243.26
• InChiKey: BBAKPUFORQONAR-ANZWQOBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,6R,7S,8aR)-1,2-dihydroxy-6,7-(isopropylidene)dioxy-3-oxo-indolizidine 在 dimethyl sulfide borane 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 48.0h， 生成 (1R,2R,6R,7S,8aR)-1,2,6,7-bis[(isopropylidene)dioxy]-indolizidine
  参考文献：
  名称：

  A chiral hexahydroindolizine as key intermediate in the synthesis of tri- and tetrahydroxyindolizidines

  摘要：

  The highly stereoselective functionalization of hexahydro-3-oxo-indolizine 6 has been examined. The bishydroxylated product can be transformed successfully into the trihydroxyindolizidine 11 in 57% overall yield. in addition, a simple elimination process to give the a,P-unsaturated lactam 13 and a second highly stereoselective bishydroxylation can be used to synthesise the tetrahydroxyindolizidine 19 in 30% overall yield. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(00)01034-6
• 作为产物：
  描述：

  (1R,8aR)-1-(tert-Butyl-dimethyl-silanyloxy)-1,5,8,8a-tetrahydro-2H-indolizin-3-one 在 potassium osmate(VI) 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 56.0h， 生成 (1R,2R,6R,7S,8aR)-1,2-dihydroxy-6,7-(isopropylidene)dioxy-3-oxo-indolizidine
  参考文献：
  名称：

  A chiral hexahydroindolizine as key intermediate in the synthesis of tri- and tetrahydroxyindolizidines

  摘要：

  The highly stereoselective functionalization of hexahydro-3-oxo-indolizine 6 has been examined. The bishydroxylated product can be transformed successfully into the trihydroxyindolizidine 11 in 57% overall yield. in addition, a simple elimination process to give the a,P-unsaturated lactam 13 and a second highly stereoselective bishydroxylation can be used to synthesise the tetrahydroxyindolizidine 19 in 30% overall yield. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(00)01034-6

文献信息

• A chiral hexahydroindolizine as key intermediate in the synthesis of tri- and tetrahydroxyindolizidines
  作者：Michael Lennartz、Eberhard Steckhan

  DOI：10.1016/s0040-4020(00)01034-6

  日期：2001.1

  The highly stereoselective functionalization of hexahydro-3-oxo-indolizine 6 has been examined. The bishydroxylated product can be transformed successfully into the trihydroxyindolizidine 11 in 57% overall yield. in addition, a simple elimination process to give the a,P-unsaturated lactam 13 and a second highly stereoselective bishydroxylation can be used to synthesise the tetrahydroxyindolizidine 19 in 30% overall yield. (C) 2001 Published by Elsevier Science Ltd.