3-hydroxy-6-methoxy-3-trimethylsilyl-1,3-dihydroindol-2-one | 599185-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-hydroxy-6-methoxy-3-trimethylsilyl-1,3-dihydroindol-2-one
• 英文别名: 3-hydroxy-6-methoxy-3-(trimethylsilylmethyl)-1H-indol-2-one
• CAS: 599185-53-2
• 化学式: C₁₃H₁₉NO₃Si
• 分子量: 265.384
• InChiKey: QTFSDPDVMVVVRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-6-methoxy-3-trimethylsilyl-1,3-dihydroindol-2-one 在 palladium dihydroxide 、 palladium on activated charcoal 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 溶剂黄146 、 正丁醛 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 (2S,3S,5aS,10aS)-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 reglocontrolled and stereocontrolled manner in a single step.

  DOI：

  10.1021/ol0351910
• 作为产物：
  描述：

  6-甲氧基靛红 、 trimethylsilylmethyllithium 以 四氢呋喃 、 正戊烷 为溶剂， 反应 3.0h， 生成 3-hydroxy-6-methoxy-3-trimethylsilyl-1,3-dihydroindol-2-one
  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

• 10.1002/cjoc.202400410
  作者：Jia, Feng-Cheng、Yuan, Zi-Yi、Luo, Na、Gu, Shuang-Xi、Hu, Xiao-Qiang

  DOI：10.1002/cjoc.202400410

  日期：——

  tolerance (> 50 examples). Mechanistic experiments revealed that this reaction involved a Peterson olefination, Michael addition and intramolecular C(sp3) arylation cascade. The variegated synthetic derivatization of target products and successful construction of bioactive molecules further illustrate the synthetic potential in spirooxindole-related drug discovery.

  螺氧吲哚的简洁组装具有重要意义，但在现代有机合成中是一项具有挑战性的任务。本文描述的是很少使用的盐丁衍生的 β-甲硅烷基甲醇与 o-卤素芳香酮的不寻常的碱促进 [4+2] 螺缩氢，它能够快速和模块化地合成六元碳环螺吲哚，产量高，具有优异的官能团耐受性（> 50个例子）。机理实验表明，该反应涉及 Peterson 烯化、Michael 加成和分子内 C（sp3） 芳基化级联反应。靶产品的杂色合成衍生化和生物活性分子的成功构建进一步说明了螺吲哚相关药物发现的合成潜力。
• 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.