(1R,2R,6R,7S,8aR)-1,2,6,7-bis[(isopropylidene)dioxy]-3-oxo-indolizidine | 334022-72-9

• 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)-1,2,6,7-bis[(isopropylidene)dioxy]-3-oxo-indolizidine
• 英文别名: (3R,7S,9R,10R,14R)-5,5,12,12-tetramethyl-4,6,11,13-tetraoxa-1-azatetracyclo[7.6.0.03,7.010,14]pentadecan-15-one
• CAS: 334022-72-9
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: YLYZFIMPRWUQOY-RCZSTQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,6R,7S,8aR)-1,2,6,7-bis[(isopropylidene)dioxy]-3-oxo-indolizidine 在 dimethyl sulfide borane 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (1R,2R,6R,7S,8aR)-1,2,6,7-tetrahydroxy-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 104.0h， 生成 (1R,2R,6R,7S,8aR)-1,2,6,7-bis[(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.