1-(2-(1H-indol-3-yl)ethyl)piperdine-2,6-dione | 59048-76-9

• 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
• 英文名称: 1-(2-(1H-indol-3-yl)ethyl)piperdine-2,6-dione
• 英文别名: 1-[2-(1H-indol-3-yl)ethyl]piperidin-2,6-dione；N-glutarimidotryptamine；1-(2-indol-3-yl-ethyl)-piperidine-2,6-dione；N-(2-Indol-3-yl-ethyl)-glutarimid；1-(2-(1H-Indol-3-yl)ethyl)-2,6-piperidinedione；1-[2-(1H-indol-3-yl)ethyl]piperidine-2,6-dione
• CAS: 59048-76-9
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: KBAAEBGRXDBBHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  524.1±33.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-(1H-indol-3-yl)ethyl)piperdine-2,6-dione 以91%的产率得到
  参考文献：
  名称：

  ATTA-UR-RAHMAN; WAHEED N., Z. NATURFORSCH. , 1976, 31B, NO 2, 287-288

  摘要：

  DOI：
• 作为产物：
  描述：

  戊二酸酐 、 2-(2-氨基乙基)吲哚 以 甲苯 为溶剂， 反应 12.0h， 以67%的产率得到1-(2-(1H-indol-3-yl)ethyl)piperdine-2,6-dione
  参考文献：
  名称：

  Syntheses of fused tetrahydro-β-carboline analogues through imide carbonyl activation using BBr3: Evidence for the involvement of fused cyclic N-acyliminium ion intermediate

  摘要：

  单晶 X 射线衍射证实了在苯乙基邻苯二甲酰亚胺的亚胺羰基活化反应中生成的融合环 N-酰亚胺离子。路易斯酸辅助亚胺羰基活化方法被成功地扩展到从相应的 N-吲哚乙亚胺合成融合的四氢-β-咔啉单元。

  DOI：

  10.1007/s12039-015-0836-8

文献信息

• Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups
  作者：Karthick Govindan、Nian-Qi Chen、Yu-Wei Chuang、Wei-Yu Lin

  DOI：10.1021/acs.orglett.1c03541

  日期：2021.12.17

  We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through

  我们报告了一组新的反应，该反应基于通过用烯丙基溴进行简单处理来解锁酰胺，为获得各种含氮官能团（如伯酰胺、磺胺、伯胺、N-酰基化合物）创造了一个通用平台。酯、硫酯、酰胺）和N-磺酰基酯。该方法具有潜在的工业实用性，如通过克级规模的分批和连续流动系统合成所证明的那样。
• Enantioselective Pictet−Spengler-Type Cyclizations of Hydroxylactams:  H-Bond Donor Catalysis by Anion Binding
  作者：Izzat T. Raheem、Parvinder S. Thiara、Emily A. Peterson、Eric N. Jacobsen

  DOI：10.1021/ja076179w

  日期：2007.11.1

  indolizinone and quinolizinone products are obtained in the thiourea-catalyzed cyclization of tryptamine-derived hydroxylactams. Substituent and counterion effect studies point to a novel mechanism of catalysis involving rate-limiting anion abstraction and binding by the thiourea.

  在硫脲催化的色胺衍生的羟基内酰胺的环化中获得高度对映体富集的吲哚嗪酮和喹嗪酮产物。取代基和反离子效应研究指出了一种新的催化机制，涉及限速阴离子提取和硫脲结合。
• Organocatalytic Enantioselective Functionalization of Cyclic α-Hydroxyamides: Access to Chiral Cyclic Imides and Azapolycyclic Compounds
  作者：Xiao-Qian Zhang、Yuan-Ren Ma、Yan-Kai Liu

  DOI：10.1021/acs.orglett.3c03182

  日期：2023.11.24

  convert unfunctionalized cyclic α-hydroxyamides into chiral cyclic α-hydroxyamides by reacting with vinyl sulfones, which could be used as versatile azacyclic synthons in the following sequences: (1) as the precursors of cyclic N-acyliminium ions to prepare natural productlike chiral azapolycyclic compounds under acidic conditions and (2) to construct chiral cyclic imides bearing unilateral substituents

  开发了一种高效的对映选择性烯胺催化不对称共轭加成，可通过与乙烯基砜反应将未官能化的环状 α-羟基酰胺直接转化为手性环状 α-羟基酰胺，可按以下顺序用作通用的氮杂环合成子：（1）环状N-酰亚胺离子的前驱体在酸性条件下制备天然产物类手性氮杂多环化合物；(2)通过氧化反应诱导的形式去对称化构建带有单侧取代基的手性环状酰亚胺。
• Peptide derivatives or pharmaceutically acceptable salts thereof, method for producing the same, use of said derivatives and pharmaceutical composition
  申请人：Nebolsin, Vladimir Evgenievich

  公开号：EP2229935A1

  公开（公告）日：2010-09-22

  Derivatives of peptides of general formula or pharmaceutically acceptable salts thereof, their use as the agents possessing antioxidant, antiasthmatic, antihypoxic, antiinflammatory, antiviral, antibacterial, lipid-regulating, antitumor, antimetastatic, glucose lowering, adaptogenic and the other kinds of therapeutic effects, a method to produce them, a pharmaceutical composition or a cosmetic agent comprising as an active agent a peptide derivative of formula (I) or pharmaceutically or cosmetically acceptable salts thereof as well as a method of therapy or prevention of diseases.

  通式肽的衍生物 或其药学上可接受的盐，它们作为具有抗氧化、抗通气、抗缺氧、抗炎、抗病毒、抗菌、调节血脂、抗肿瘤、抗转移、降糖、适应性和其他各种治疗效果的制剂的用途，生产它们的方法，包含式 (I) 肽衍生物或其药学上或化妆品学上可接受的盐作为活性剂的药物组合物或化妆品制剂，以及治疗或预防疾病的方法。
• GLUTARIMIDE DERIVATIVES, USE THEREOF, PHARMACEUTICAL COMPOSITION BASED THEREON AND METHODS FOR PRODUCING GLUTARIMIDE DERIVATIVES
  申请人：Obschestvo S Ogranichennoi Otvetstennostiyu "Pharmenterprises"

  公开号：EP2985282A1

  公开（公告）日：2016-02-17

  The present invention relates to novel biologically active glutarimide derivatives of general formula I or pharmaceutically acceptable salts thereof, their use as an agent for the treatment of upper respiratory tract diseases, pharmaceutical compositions comprising the glutarimide derivatives of general formula I, methods for preparing the glutarimide derivatives of general formula I by heating a dicarboxylic acid monoamide of general formula II with a dehydrating agent.

  本发明涉及通式Ⅰ的新型生物活性戊二酰亚胺衍生物或其药学上可接受的盐、它们作为治疗上呼吸道疾病的制剂的用途、包含通式Ⅰ的戊二酰亚胺衍生物的药物组合物、通过用脱水剂加热通式Ⅱ的二羧酸单酰胺来制备通式Ⅰ的戊二酰亚胺衍生物的方法。