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2-(3-hydroxy-2-oxoindolin-3-yl)acetonitrile | 137761-24-1

中文名称
——
中文别名
——
英文名称
2-(3-hydroxy-2-oxoindolin-3-yl)acetonitrile
英文别名
(+/-)-3-cyanomethyl-3-hydroxyoxindole;(-)-3-Cyanomethyl-3-hydroxy-1H-indol-2(3H)-one;2-(3-hydroxy-2-oxo-1H-indol-3-yl)acetonitrile
2-(3-hydroxy-2-oxoindolin-3-yl)acetonitrile化学式
CAS
137761-24-1
化学式
C10H8N2O2
mdl
MFCD24388933
分子量
188.186
InChiKey
IXOBWMNTICTXOJ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    511.3±50.0 °C(Predicted)
  • 密度:
    1.369±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    0.3
  • 重原子数:
    14
  • 可旋转键数:
    1
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.2
  • 拓扑面积:
    73.1
  • 氢给体数:
    2
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-(3-hydroxy-2-oxoindolin-3-yl)acetonitrile 在 sodium tetrahydroborate 、 caesium carbonate 、 nickel dichloride 作用下, 以 甲醇N,N-二甲基甲酰胺乙腈 为溶剂, 反应 5.5h, 生成 tert-butyl (2-(3-methoxy-1-methyl-2-oxoindolin-3-yl)ethyl)carbamate
    参考文献:
    名称:
    A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids
    摘要:
    A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (+/-)-alline and (+/-)-CPC-1 were achieved using this methodology.
    DOI:
    10.1021/ol200547m
  • 作为产物:
    描述:
    参考文献:
    名称:
    A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids
    摘要:
    A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (+/-)-alline and (+/-)-CPC-1 were achieved using this methodology.
    DOI:
    10.1021/ol200547m
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文献信息

  • Preparation of cruciferous phytoalexin related metabolites, (−)-dioxibrassinin and (−)-3-cyanomethyl-3-hydroxyoxindole, and determination of their absolute configurations by vibrational circular dichroism (VCD)
    作者:Kenji Monde、Tohru Taniguchi、Nobuaki Miura、Shin-Ichiro Nishimura、Nobuyuki Harada、Rina K Dukor、Laurence A Nafie
    DOI:10.1016/s0040-4039(03)01513-2
    日期:2003.8
    metabolites, ()-dioxibrassinin (1) and ()-3-cyanomethyl-3-hydroxyoxindole (2) were prepared from isatin as racemates and were resolved by chiral HPLC. Their absolute configurations were determined by the new chiroptical technique, vibrational circular dichroism (VCD), as well as by the conventional electronic circular dichroism (ECD). It is concluded that the absolute configurations of the naturally
    十字花科植物抗毒素相关代谢物(-)-dioxibrassinin(1)和(-)-3-cyanomethyl-3-hydroxyoxindole(2)是由伊斯汀​​作为外消旋物制备的,并通过手性HPLC拆分。它们的绝对构型由新的按摩技术,振动圆二色性(VCD)以及常规电子圆二色性(ECD)确定。可以得出结论,自然存在的(-)- 1和(-)- 2的绝对构型均为S。
  • Krapcho Dealkoxycarbonylation Strategy of Ethyl Cyanoacetate for the Synthesis of 3-Hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-Dicyanomethyl-2-oxindoles in a Reaction with Isatin
    作者:Keshri Nath Tiwari、Chandran R.
    DOI:10.1055/s-0040-1707816
    日期:2020.8
    A new strategy for the synthesis of 3-hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-dicyanomethyl-2-oxindoles in a reaction of isatin with ethyl cyanoacetate by Krapcho dealkoxycarbonylation reaction in aqueous media is demonstrated. The reaction provides an easy access to synthetically and medicinally valuable oxindole alkylnitriles in good to very good yields. Wider substrate scope and operationally
    提出了一种在性介质中通过Krapcho脱氧羰基羰基化反应在靛红乙酸乙酯反应中合成3-羟基-3-基甲基-2-氧吲哚和3,3'-二基甲基-2-氧吲哚的新策略。该反应提供了易于获得的合成和医学上有价值的羟吲哚烷基腈,收率很高。较宽的基板范围和操作简单的实验程序是已开发协议的突出特点。在控制实验的基础上,合理化了的反应机理和协同效应。
  • Copper-Catalyzed Asymmetric Addition to Isatins to give 3-Hydroxy-2-oxindoles by C-H Activation
    作者:Tao Deng、Hongjun Wang、Chun Cai
    DOI:10.1002/ejoc.201402852
    日期:2014.11
    A copper-catalyzed asymmetric addition to isatins to give 3-hydroxy-2-oxindoles by C–H activation with a fluorous bis(oxazoline) as ligand is presented. The corresponding products were obtained in 35–66 % yields with enantioselectivities up to 92 %. The fluorous ligand can be easily recovered and reused at least three times without significant loss in its activity.
    催化不对称加成到靛红,通过 C-H 活化得到 3-羟基-2-羟吲哚,以代双(恶唑啉)作为配体。相应产品的产率为 35-66%,对映选择性高达 92%。含配体可轻松回收并重复使用至少 3 次,而不会显着降低其活性。
  • An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp<sup>3</sup>)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones
    作者:Venkatachalam Rajeshkumar、Selvaraj Chandrasekar、Govindasamy Sekar
    DOI:10.1039/c4ob01564a
    日期:——
    A novel molecular I2-catalyzed synthesis of isatins through C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones with excellent yields up to 97% under transition metal, base, additive, peroxide and ligand free conditions is described. The present protocol is suitable for gram scale synthesis of isatins and retained its high yield. Further, the synthetic utility of this
    通过C(sp 3)–H氧化和2'-苯乙酮的分子内C–N键形成的新型分子I 2催化的靛红合成,在不含过渡属,碱,添加剂,过氧化物和配体的情况下,产率高达97%描述了条件。本协议适用于伊斯汀的克规模合成,并保持其高产率。此外,证明了该反应对生物活性3-羟基-2-氧吲哚和氧吲哚的合成的合成效用。
  • An efficient aldol-type direct reaction of isatins with TMSCH<sub>2</sub>CN
    作者:V. U. Bhaskara Rao、Krishna Kumar、Ravi P. Singh
    DOI:10.1039/c5ob01560j
    日期:——

    Cesium fluoride catalyzed direct cyanomethylation of various isatins by using trimethylsilyl acetonitrile (TMSAN) as a nucleophile has been developed. The reaction has been explored for a number of isatins, with various substitutions on its aromatic ring. Further, the versatility of the reaction is demonstrated by converting the direct aldol adducts to various corresponding intermediates.

    通过使用三甲基乙腈TMSAN)作为亲核试剂,氟化铯催化的直接甲基化反应已被开发用于各种吲哚酮的反应。该反应已经应用于多种带有芳环取代的吲哚酮。此外,通过将直接醛醇加合物转化为各种相应的中间体,证明了该反应的多功能性。
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