(R)-3-amino-3-methylindolin-2-one | 1207340-49-5

• 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: (R)-3-amino-3-methylindolin-2-one
• 英文别名: (R)-3-amino-3-methyl-1,3-dihydro-indol-2-one；(R)-3-amino-3-methyl-2-oxindole；(R)-3-amino-3-methyloxindole；(3R)-3-amino-3-methyl-1H-indol-2-one
• CAS: 1207340-49-5
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: XUFMKAUTDNWVRR-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘苯 、 (R)-3-amino-3-methylindolin-2-one 在 copper(I) oxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 72.0h， 以10%的产率得到(R)-3-methyl-3-(phenylamino)indolin-2-one
  参考文献：
  名称：

  简便，有效的对映选择性羟胺化反应：使用亚硝基芳烃合成3-羟基氨基-2-氧代吲哚

  摘要：

  Sc发挥作用：使用Sc（OTf）3 / L1络合物实现了N-未保护的2-氧吲哚与亚硝基芳烃的高度对映选择性羟基胺化反应。该催化剂体系表现出显着的底物范围和高效率。该转化是手性Sc III /烯酸酯活化亚硝基芳烃的第一个实例，并且可以以克级进行，而不会损失ee 值。

  DOI：

  10.1002/anie.201100758
• 作为产物：
  描述：

  3-bromo-3-methylindolin-2-one 在 ammonium cerium (IV) nitrate 、 nickel(II) tetrafluoroborate hexahydrate 、 C₄₂H₆₆N₄O₈ 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 24.92h， 生成 (R)-3-amino-3-methylindolin-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of 3‐Substituted 3‐Amino‐2‐oxindoles by Amination with Anilines

  摘要：

  AbstractA chiral N,N′‐dioxide‐nickel(II) complex‐catalyzed asymmetric amination of 3‐bromo‐3‐substituted oxindoles with anilines has been developed. A series of alkyl or aryl 3‐amino‐indolinones with quaternary stereocenters were obtained in high yields with excellent ee values in one step (up to 99 % yield, up to 96 % ee). The method provided a ready route to optically active intermediates of 3‐amino‐2‐oxindole‐based bioactive compounds. Moreover, a possible transition‐state model is proposed so as to elucidate the origin of the chirality based on the X‐ray crystal structure of the catalyst and the adduct.

  DOI：

  10.1002/chem.202100829

文献信息

• Highly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric α-Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex
  作者：Zhigang Yang、Zhen Wang、Sha Bai、Ke Shen、Donghui Chen、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1002/chem.201000126

  日期：2010.6.11

  A highly enantioselective α‐amination of 3‐substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf)3/N,N′‐dioxide complex (Tf: triflate) has been developed and affords the corresponding 3‐amino‐2‐oxindole derivatives in high yields (up to 98 %) with excellent enantioselectivities (up to 99 % ee). The procedure is capable of tolerating a relatively wide range of substrates, and excellent

  已开发出由手性Sc（OTf）3 / N，N'-二氧化物络合物（Tf：三氟甲磺酸酯）催化的偶氮二羧酸酯对3-取代的羟吲哚的高对映选择性α-胺化反应，并提供相应的3-氨基-2-氧吲哚衍生物高收率（高达98％）和优异的对映选择性（高达99％ee）。该程序能够耐受相对广泛的底物，并获得优异的结果（92–96％ee即使在温和的条件下存在0.5mol％的催化剂负载量，也可以得到）。这些结果表明了催化方法的潜在价值。此外，由于具有较高的合成通用性，因此该产品可以轻松转变为带有手性季立体中心的旋光性3-氨基-3-甲基羟吲哚。
• Mouri, Shinsuke; Chen, Zhihua; Mitsunuma, Harunobu, Journal of the American Chemical Society, 2010, vol. 132, p. 1255 - 1257
  作者：Mouri, Shinsuke、Chen, Zhihua、Mitsunuma, Harunobu、Furutachi, Makoto、Matsunaga, Shigeki、Shibasaki, Masakatsu

  DOI：——

  日期：——
• Enantioselective Synthesis of 3‐Substituted 3‐Amino‐2‐oxindoles by Amination with Anilines
  作者：Wenkun Yang、Pei Dong、Jian Xu、Jian Yang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/chem.202100829

  日期：2021.6.25

  AbstractA chiral N,N′‐dioxide‐nickel(II) complex‐catalyzed asymmetric amination of 3‐bromo‐3‐substituted oxindoles with anilines has been developed. A series of alkyl or aryl 3‐amino‐indolinones with quaternary stereocenters were obtained in high yields with excellent ee values in one step (up to 99 % yield, up to 96 % ee). The method provided a ready route to optically active intermediates of 3‐amino‐2‐oxindole‐based bioactive compounds. Moreover, a possible transition‐state model is proposed so as to elucidate the origin of the chirality based on the X‐ray crystal structure of the catalyst and the adduct.
• Facile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3-Hydroxyamino-2-Oxindoles Using Nitrosoarenes
  作者：Ke Shen、Xiaohua Liu、Gang Wang、Lili Lin、Xiaoming Feng

  DOI：10.1002/anie.201100758

  日期：2011.5.9

  Sc takes action: The highly enantioselective hydroxyamination reaction of N‐unprotected 2‐oxindoles with nitrosoarenes has been realized using the Sc(OTf)3/L1 complex. The catalyst system exhibited remarkably broad substrate scope and high efficiency. This transformation is the first example of a chiral ScIII/enolate activating a nitrosoarene, and can be conducted on a gram scale without loss in the

  Sc发挥作用：使用Sc（OTf）3 / L1络合物实现了N-未保护的2-氧吲哚与亚硝基芳烃的高度对映选择性羟基胺化反应。该催化剂体系表现出显着的底物范围和高效率。该转化是手性Sc III /烯酸酯活化亚硝基芳烃的第一个实例，并且可以以克级进行，而不会损失ee 值。