methyl 1-(3-methylbut-2-en-1yl)-2,3-dioxoindoline-6-carboxylate | 1298119-48-8

• 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: methyl 1-(3-methylbut-2-en-1yl)-2,3-dioxoindoline-6-carboxylate
• CAS: 1298119-48-8
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: BXLPGHGOXGKHCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 1-(3-methylbut-2-en-1yl)-2,3-dioxoindoline-6-carboxylate 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 1.58h， 生成 methyl 3-(cyanomethyl)-1-(3-methylbut-2-en-1-yl)-2-oxoindoline-6-carboxylate
  参考文献：
  名称：

  Exercising Regiocontrol in Palladium-Catalyzed Asymmetric Prenylations and Geranylation: Unifying Strategy toward Flustramines A and B

  摘要：

  Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using pi-geranylpalladium complexes.

  DOI：

  10.1021/ja2020873
• 作为产物：
  描述：

  6-溴靛红 在 1,3-双(二苯基膦)丙烷 、 palladium diacetate 、 sodium hydride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 20.17h， 生成 methyl 1-(3-methylbut-2-en-1yl)-2,3-dioxoindoline-6-carboxylate
  参考文献：
  名称：

  Exercising Regiocontrol in Palladium-Catalyzed Asymmetric Prenylations and Geranylation: Unifying Strategy toward Flustramines A and B

  摘要：

  Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using pi-geranylpalladium complexes.

  DOI：

  10.1021/ja2020873