(2S,3S,5aS,10aR)-1',2',5a,6,7,8,10,10a-octahydro-6'-methoxy-3-(2-methoxy-2-methylpropyl)-2',5,10-trioxospiro[1H,5H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole] | 599185-57-6

• 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: (2S,3S,5aS,10aR)-1',2',5a,6,7,8,10,10a-octahydro-6'-methoxy-3-(2-methoxy-2-methylpropyl)-2',5,10-trioxospiro[1H,5H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole]
• 英文别名: (3R,5S,6S,9S)-6'-methoxy-6-(2-methoxy-2-methylpropyl)spiro[1,7-diazatricyclo[7.3.0.03,7]dodecane-5,3'-1H-indole]-2,2',8-trione
• CAS: 599185-57-6
• 化学式: C₂₃H₂₉N₃O₅
• 分子量: 427.5
• InChiKey: WEGIXJDXHFIFPE-FXKZBUDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,5aS,10aR)-1',2',5a,6,7,8,10,10a-octahydro-6'-methoxy-3-(2-methoxy-2-methylpropyl)-2',5,10-trioxospiro[1H,5H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole] 在 水 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以44%的产率得到(2S,3S,5aS,10aR)-1',2',5a,6,7,8,10,10a-octahydro-6'-methoxy-3-(2-methyl-1-propenyl)-2',5,10-trioxospiro[1H,5H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole]
  参考文献：
  名称：

  Concise, Asymmetric Total Synthesis of Spirotryprostatin A

  摘要：

  The structurally intriguing cell-cycle inhibitor spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived oxindole moiety that has been created in a reglocontrolled and stereocontrolled manner in a single step.

  DOI：

  10.1021/ol0351910
• 作为产物：
  描述：

  L-脯氨酸苄酯盐酸盐 在 palladium on activated charcoal 盐酸 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 212.0h， 生成 (2S,3S,5aS,10aR)-1',2',5a,6,7,8,10,10a-octahydro-6'-methoxy-3-(2-methoxy-2-methylpropyl)-2',5,10-trioxospiro[1H,5H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole]
  参考文献：
  名称：

  Concise, asymmetric total synthesis of spirotryprostatin A

  摘要：

  The structurally intriguing cell-cycle inhibitor spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived oxindole moiety that has been created in a regiocontrolled and stereocontrolled manner in a single step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.047

文献信息

• Concise, Asymmetric Total Synthesis of Spirotryprostatin A
  作者：Tomoyuki Onishi、Paul R. Sebahar、Robert M. Williams

  DOI：10.1021/ol0351910

  日期：2003.8.1

  The structurally intriguing cell-cycle inhibitor spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived oxindole moiety that has been created in a reglocontrolled and stereocontrolled manner in a single step.
• Concise, asymmetric total synthesis of spirotryprostatin A
  作者：Tomoyuki Onishi、Paul R. Sebahar、Robert M. Williams

  DOI：10.1016/j.tet.2004.07.047

  日期：2004.10

  The structurally intriguing cell-cycle inhibitor spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived oxindole moiety that has been created in a regiocontrolled and stereocontrolled manner in a single step. (C) 2004 Elsevier Ltd. All rights reserved.