6-甲基吲哚酮 | 56341-38-9

• 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
• 中文名称: 6-甲基吲哚酮
• 中文别名: 6-甲基-2-吲哚啉酮
• 英文名称: 6-methylindolin-2-one
• 英文别名: 6-Methyl-oxindol；6-methyl-1,3-dihydroindol-2-one
• CAS: 56341-38-9
• 化学式: C₉H₉NO
• mdl: MFCD08457972
• 分子量: 147.177
• InChiKey: BFCDUCCWAPLDJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  179-180 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  315.0±41.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  6-甲基吲哚酮 在 palladium on activated charcoal tetraphosphorus decasulfide 、 硫酸 、 氢气 、 sodium ethanolate 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 为溶剂， 生成 3-(6-Methyl-2-thioxo-2,3-dihydro-1H-indol-3-yl)-propionic acid ethyl ester
  参考文献：
  名称：

  Tyrosine kinase inhibitors. 1. Structure-activity relationships for inhibition of epidermal growth factor receptor tyrosine kinase activity by 2,3-dihydro-2-thioxo-1H-indole-3-alkanoic acids and 2,2'-dithiobis(1H-indole-3-alkanoic acids)

  摘要：

  A series of 2,3-dihydro-2-thioxo-1H-indole-3-alkanoic acids, and their methyl esters were prepared, the majority by oxidation of 1H-indole-3-alkanoic acids (DMSO/HCl), followed by thiation of the corresponding 2,3-dihydro-2-oxo-1H-indole-3-alkanoic acid esters. The monomeric thiones undergo facile and reversible oxidation to the corresponding 2,2'-dithiobis(1H-indole-3-alkanoic acids). The compounds were evaluated for their abilities to inhibit the tyrosine kinase activity of the epidermal growth factor receptor using a native complex contained in plasma membrane vesicles shed from cultured A431 cells, and to inhibit the growth of Swiss 3T3 mouse fibroblast in culture. Enzyme inhibitory activity is dependent on the length of the side chain, with propanoic acid derivatives showing the highest activity. The acids are generally significantly more potent than the corresponding esters, and the disulfides more active than the corresponding monomers. An ability to undergo the thione-thiol tautomerism necessary for dimerization is essential, with 3,3-disubstituted compounds being inactive. Overall, the data suggest that the disulfide is the more active form, with much of the activity of the monomeric thiones being due to varying degrees of conversion to the disulfide during the assay. In the growth inhibition assay, the methyl esters are more potent than their corresponding carboxylic acids, and the dimers are generally more potent than the monomers. The data show these compounds to be a novel and potent class of inhibitors of epidermal growth factor receptor tyrosine kinase activity.

  DOI：

  10.1021/jm00069a003
• 作为产物：
  描述：

  4-甲基-2-硝基苯乙酸 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以82 %的产率得到6-甲基吲哚酮
  参考文献：
  名称：

  通过 SmI2 促进的 2-硝基苯乙酸还原合成羟吲哚

  摘要：

  首次报道了 SmI2 促进 2-硝基苯乙酸还原为羟吲哚的过程。该反应涉及硝基的还原，通过 N-O 键断裂并与邻近的羧基直接缩合进行。从合成的角度来看，开发了一种在温和中性条件下合成羟吲哚的新方法。

  DOI：

  10.1055/a-2175-1008

文献信息

• [EN] HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF STRESS-RELATED CONDITIONS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES POUR LE TRAITEMENT D'ÉTATS LIÉS AU STRESS
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2010137738A1

  公开（公告）日：2010-12-02

  The present invention provides a novel heterocyclic compound. A heterocyclic compound represented by general formula (1) wherein, R1 and R2, each independently represent hydrogen; a phenyl lower alkyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group and the like on a benzene ring and/or a lower alkyl group; or a cyclo C3-C8 alkyl lower alkyl group; or the like; R3 represents a lower alkynyl group or the like; R4 represents a phenyl group that may have a substituent(s) selected from the group consisting of a 1,3,4-oxadiazolyl group that may have e.g., halogen or a heterocyclic group selected from pyridyl group and the like; the heterocyclic group may have at least one substituent(s) selected from a lower alkoxy group and the like or a salt thereof.

  本发明提供了一种新颖的杂环化合物。一种由通式（1）表示的杂环化合物，其中，R1和R2分别独立表示氢；苯基较低烷基基团，可能在苯环和/或较低烷基基团上具有从较低烷基基团等组成的取代基；或环C3-C8烷基较低烷基基团；或类似物；R3表示较低炔基基团或类似物；R4表示可能具有从1,3,4-噁二唑基团（例如，卤素）或从吡啶基团等组成的取代基的苯基团；所述杂环基可能具有至少一个从较低烷氧基等选择的取代基或其盐。
• Palladium-Catalyzed C–H Activation and Cyclization of Anilides with 2-Iodoacetates and 2-Iodobenzoates: An Efficient Method toward Oxindoles and Phenanthridones
  作者：Chien-Hong Cheng、Parthasarathy Gandeepan、Pachaiyappan Rajamalli

  DOI：10.1055/s-0035-1561856

  日期：——

  Abstract A concise approach to the synthesis of oxindoles and phenanthridones from anilides is described. In the presence of catalytic amount of Pd(OAc)2, 2-iodoacetates and 2-iodobenzoates can be used to functionalize ortho C–H bond of anilides, which subsequently undergo intramolecular cyclization to give the products. A possible reaction mechanism that involves a PdII/PdIV catalytic cycle is proposed

  摘要 描述了一种由苯胺合成羟吲哚和菲啶酮的简洁方法。在存在催化量的Pd（OAc）2的情况下，可以使用2-碘乙酸酯和2-碘苯甲酸酯官能化苯甲酸酯的邻位C-H键，随后进行分子内环化以生成产物。在详细的机理研究的支持下，提出了可能的涉及Pd II / Pd IV催化循环的反应机理。 描述了一种由苯胺合成羟吲哚和菲啶酮的简洁方法。在存在催化量的Pd（OAc）2的情况下，可以使用2-碘乙酸酯和2-碘苯甲酸酯官能化苯甲酸酯的邻位C-H键，随后进行分子内环化以生成产物。在详细的机理研究的支持下，提出了可能的涉及Pd II / Pd IV催化循环的反应机理。
• A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole‐Fused Oxacycles
  作者：Min Gao、Yanshu Luo、Qianlan Xu、Yukun Zhao、Xiangnan Gong、Yuanzhi Xia、Lin Hu

  DOI：10.1002/anie.202105282

  日期：2021.9

  A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C−C and the subsequent umpolung C−O bond-forming reactions with one-carbon unit nucleophiles, thus providing

  在手性相转移催化剂 (PTC) 的存在下，已经实现了羟吲哚与双官能过氧化物的统一催化不对称 ( N +1) ( N =4, 5) 环化反应。这种通用策略利用过氧化物作为独特的双亲电四原子或五原子合成子参与 C−C 和随后与单碳单元亲核试剂的 umpolung C−O 键形成反应，从而提供了一种独特的方法来获得有价值的手性螺吲哚-四氢呋喃和-四氢吡喃在温和条件下具有良好的产率和高对映选择性。进行 DFT 计算以合理化高对映选择性的起源。还证明了所得产物的克级合成和合成效用。
• Spiroindolinone Derivatives
  申请人：Ding Qingjie

  公开号：US20090156610A1

  公开（公告）日：2009-06-18

  There are provided compounds of the formula and pharmaceutically acceptable salts and esters thereof wherein W, V, X, Y, A, R and R′ are as described herein. The compounds are useful as anticancer agents.

  提供的化合物的公式为 及其药用可接受的盐和酯 其中W、V、X、Y、A、R和R'如本文所述。 这些化合物可用作抗癌药物。
• BROMODOMAIN INHIBITORS
  申请人：Quanticel Pharmaceuticals

  公开号：US20150111885A1

  公开（公告）日：2015-04-23

  The present invention relates to substituted heterocyclic derivative compounds, compositions comprising said compounds, and the use of said compounds and compositions for epigenetic regulation by inhibition of bromodomain-mediated recognition of acetyl lysine regions of proteins, such as histones. Said compositions and methods are useful for the treatment of cancer and neoplastic disease.

  本发明涉及替代杂环衍生物化合物，包括所述化合物的组合物，以及通过抑制溴结构域介导的蛋白质乙酰赖氨酸区域的识别来进行表观遗传调控的所述化合物和组合物的用途。所述组合物和方法对于癌症和肿瘤性疾病的治疗是有用的。