3-hydroxy-5-iodo-3-methylindolin-2-one | 1449699-14-2

• 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: 3-hydroxy-5-iodo-3-methylindolin-2-one
• 英文别名: 3-hydroxy-5-iodo-3-methyl-1H-indol-2-one
• CAS: 1449699-14-2
• 化学式: C₉H₈INO₂
• 分子量: 289.073
• InChiKey: GEVSBEQNIIHFIE-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250 °C
• 沸点：
  441.3±45.0 °C(Predicted)
• 密度：
  1.946±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-iodo-3-methylindolin-2-one 在 三溴化磷 作用下， 以 四氢呋喃 为溶剂， 生成 C₉H₇BrINO
  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
• 作为产物：
  描述：

  5-碘吲哚醌 、 甲基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 3-hydroxy-5-iodo-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

• Substituted Oxindole Derivatives, Medicaments Containing Said Derivatives and Use Thereof
  申请人：Lubisch Wilfried

  公开号：US20120115842A1

  公开（公告）日：2012-05-10

  The invention relates to novel oxindole derivatives of general formula (I), wherein substituents A, B, X and Y are defined as in claim 1 , medicaments containing said derivatives, and the use thereof in the prophylaxis and/or treatment of vasopressin-dependent and/or oxytocin-dependent diseases.

  该发明涉及一种一般式（I）的新型氧吲哚衍生物，其中取代基A、B、X和Y的定义如权利要求书中，包含该衍生物的药物，以及在预防和/或治疗依赖于加压素和/或催产素的疾病中的使用。
• SUBSTITUTED OXINDOLE DERIVATIVES AND THEIR USE AS VASOPRESSIN AND/OR OXYTOCIN RECEPTOR LIGANDS
  申请人：Geneste Herve

  公开号：US20090318406A1

  公开（公告）日：2009-12-24

  The present invention relates to novel oxindole derivatives of general formula (I), in which the substituents R 1 , R 2 , A, B and Y are as defined in claim 1, medicinal products containing them and use thereof for the prophylaxis and/or treatment of vasopressin-dependent and/or oxytocin-dependent diseases.

  本发明涉及一种新型的氧化吲哚衍生物，其通式为(I)，其中取代基R1、R2、A、B和Y的定义如权利要求书中所述，包括含有它们的药物制剂和用于预防和/或治疗利尿激素依赖和/或催产素依赖疾病的用途。
• Asymmetric Synthesis of 3-Lactone Substituted 2-Oxindoles with Vicinal Quaternary Carbon Centers via Vinylogous Conjugate Addition
  作者：Zegong Li、Zi Zeng、Qi Tang、Ziwei Zhong、Xiaohua Liu、Xiaoming Feng

  DOI：10.1055/a-2066-2879

  日期：——

  A new method has been developed for constructing vicinal quaternary stereocenters with an oxindole–butanolide hybrid framework through asymmetric vinylogous addition of a siloxyfuran to an indol-2-one in the presence of a readily available N,N′-dioxide–Ni(OTf)2 complex catalyst. Various oxindole–lactones were obtained in up to 98% yield with >19:1 dr and 97% ee under mild reaction conditions. A possible

  开发了一种新方法，通过在容易获得的N , N ' -二氧化物-Ni(OTf)存在下，将甲硅氧呋喃不对称插烯加成到吲哚-2-酮上，从而构建具有羟吲哚-丁内酯杂化骨架的邻位季立体中心2络合物催化剂。在温和的反应条件下，以 >19:1 dr 和 97% ee 获得了高达 98% 的收率和 97% ee 的各种羟吲哚内酯。提出了一种可能的过渡态模型来解释不对称感应的起源。
• Development of Potent Microtubule Targeting Agent by Structural Simplification of Natural Diazonamide
  作者：Toms Kalnins、Viktorija Vitkovska、Mihail Kazak、Diana Zelencova-Gopejenko、Melita Ozola、Nauris Narvaiss、Marina Makrecka-Kuka、Ilona Domračeva、Artis Kinens、Baiba Gukalova、Nele Konrad、Riina Aav、Francesca Bonato、Daniel Lucena-Agell、J. Fernando Díaz、Edgars Liepinsh、Edgars Suna

  DOI：10.1021/acs.jmedchem.4c00388

  日期：2024.6.13

  The structurally simplified macrocycles are accessible in 12 steps from readily available indolin-2-one and tert-leucine with excellent diastereoselectivity (99:1 dr) in the key macrocyclization step. The most potent macrocycle acts as a tubulin assembly inhibitor and exerts similar effects on A2058 cell cycle progression and induction of apoptosis as does marketed microtubule-targeting agent vinorelbine

  海洋代谢物重氮酰胺 A 对一系列肿瘤细胞系具有低纳摩尔级细胞毒性；然而，其高度复杂的分子结构破坏了天然产物的治疗潜力。我们证明，天然重氮酰胺 A 中杂芳族大环的截断，加上用羟吲哚部分取代具有挑战性的合成四环半缩醛胺亚基，可产生复杂性大大降低的类似物，并具有改善的类药物特性和纳摩尔级抗增殖效力。结构简化的大环化合物可通过 12 个步骤从容易获得的二氢吲哚-2-酮和叔亮氨酸中获得，在关键的大环化步骤中具有出色的非对映选择性 (99:1 dr)。最有效的大环化合物作为微管蛋白组装抑制剂，对 A2058 细胞周期进程和细胞凋亡诱导产生与市售微管靶向剂长春瑞滨类似的作用。
• Catalyst-free synthesis of 3-hydroxy-3-(alkyl/aryl)indolin-2-ones by addition of organoaluminum reagents to isatins
  作者：G. Santosh Kumar、Palakuri Ramesh、A. Sanjeeva Kumar、A. Swetha、H.M. Meshram

  DOI：10.1016/j.tetlet.2013.07.027

  日期：2013.9

  An efficient synthesis of 3-hydroxy-3-(alkyl/aryl)indol-2-one derivatives has been described by the reactions of isatin with organoaluminum reagents. The reaction is very rapid and yields are high. The protocol is applicable for substituted isatins as well as a variety of organoaluminums. (C) 2013 Elsevier Ltd. All rights reserved.