(S)-tert-butyl 3-allyl-2-oxoindoline-3-carboxylate | 1092486-31-1

• 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: (S)-tert-butyl 3-allyl-2-oxoindoline-3-carboxylate
• 英文别名: tert-butyl (S)-3-allyl-2-oxoindoline-3-carboxylate；tert-butyl (3S)-2-oxo-3-prop-2-enyl-1H-indole-3-carboxylate
• CAS: 1092486-31-1
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: MMZIGOMKBGVUOZ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 3-allyl-2-oxoindoline-3-carboxylate 在 硫酸 、 sodium hydride 、 2,4-二硝基苯肼 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 methyl (S)-3-allyl-1-((((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methyl)sulfonyl)-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones

  摘要：

  In this Article, a strategy to obtain highly enantio-selective catalysts for the Claisen rearrangement of allyloxy- and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy- or proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation.

  DOI：

  10.1021/jo302039n
• 作为产物：
  描述：

  tert-butyl 2-(allyloxy)-1H-indole-3-carboxylate 在 silver hexafluoroantimonate 、 Pd[(R)-difluoroPHOS]Cl₂ 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以60%的产率得到(S)-tert-butyl 3-allyl-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  催化对映选择性 Meerwein-Eschenmoser Claisen 重排：烯丙基氧化吲哚的不对称合成

  摘要：

  第一个催化、对映选择性 Meerwein-Eschenmoser Claisen 重排已经实现。钯 (II) BINAP 或膦基恶唑啉催化剂用于生成 100% 转化率和高达 92% ee 的羟吲哚产品。

  DOI：

  10.1021/ja807026z

文献信息

• Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones
  作者：Trung Cao、Elizabeth C. Linton、Joshua Deitch、Simon Berritt、Marisa C. Kozlowski

  DOI：10.1021/jo302039n

  日期：2012.12.21

  In this Article, a strategy to obtain highly enantio-selective catalysts for the Claisen rearrangement of allyloxy- and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy- or proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation.
• Catalytic Enantioselective Meerwein−Eschenmoser Claisen Rearrangement: Asymmetric Synthesis of Allyl Oxindoles
  作者：Elizabeth C. Linton、Marisa C. Kozlowski

  DOI：10.1021/ja807026z

  日期：2008.12.3

  The first catalytic, enantioselective Meerwein-Eschenmoser Claisen rearrangement has been achieved. Palladium(II) BINAP or phosphinooxazoline catalysts were employed to generate oxindole products with 100% conversion and up to 92% ee.

  第一个催化、对映选择性 Meerwein-Eschenmoser Claisen 重排已经实现。钯 (II) BINAP 或膦基恶唑啉催化剂用于生成 100% 转化率和高达 92% ee 的羟吲哚产品。