11-methylchromeno[4,3-b]indol-6(11H)-one | 59050-52-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 11-methylchromeno[4,3-b]indol-6(11H)-one
• 英文别名: 11-Methylchromeno[4,3-b]indol-6-one
• CAS: 59050-52-1
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: NPHMABSNHRNCIE-UHFFFAOYSA-N

物化性质

• 熔点：
  251-252 °C
• 沸点：
  470.9±14.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯苯基硼酸 在 四(三苯基膦)钯 、 噻吩-2-甲酸亚铜(I) 、 四甲基乙二胺 、 sodium carbonate 、 caesium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 300.0 ℃ 、1.72 MPa 条件下， 反应 0.17h， 生成 11-methylchromeno[4,3-b]indol-6(11H)-one
  参考文献：
  名称：

  Cu(I)-mediated lactone formation in subcritical water: a benign synthesis of benzopyranones and urolithins A–C

  摘要：

  Benzopyranones were successfully synthesized using Cu(I)-mediated C-O bond formation in subcritical water. A number of benzopyranone derivatives including polymethoxy benzopyranones, benzopyranopyridones, cbromenoindolones, and furochromenones were synthesized in satisfactory yield. This methodology was further applied to synthesize the intestinal microbial metabolites, urolithins A, B, and C, which were found to exhibit potent antioxidant activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.045

文献信息

• Ligand-Controlled Palladium(II)-Catalyzed Regiodivergent Carbonylation of Alkynes: Syntheses of Indolo[3,2-<i>c</i> ]coumarins and Benzofuro[3,2-<i>c</i> ]quinolinones
  作者：Dong Ding、Guohao Zhu、Xuefeng Jiang

  DOI：10.1002/anie.201804788

  日期：2018.7.16

  O‐attack/N‐carbonylation cyclization leading to benzofuro[3,2‐c]quinolinones, while a sterically bulky and electron‐rich ligand facilitates N‐attack/O‐carbonylation cyclization to generate indolo[3,2‐c]coumarins. Furthermore, various other nucleophiles are applicable for delivering a variety of indoloquinolinones, pyranoquinolones, and chromeno[3,4‐c]quinolinones in one step, and serves as a method for creating

  通过可控制的钯（II）催化羰基化环化反应，建立了吲哚[3,2– c ]香豆素和苯并呋喃[3,2– c ]喹啉酮的区域发散性合成。化学和区域选择性仅受钯催化剂上的配体调节。缺电子配体的刚性骨架促进了O-攻击/ N-羰基化环化反应，从而导致苯并呋喃[3,2- c ]喹啉酮，而空间大且富含电子的配体则促进了N-攻击/ O-羰基化环化反应。生成indolo [3,2‐ c]香豆素。此外，其他各种亲核试剂也可用于一步传递各种吲哚喹啉酮，吡喃喹诺酮和色诺[3,4-c]喹啉酮，并且可作为创建用于药物发现的化合物库的方法。
• Weakly Coordinating <i>tert</i>-Amide-Assisted Ru(II)-Catalyzed Synthesis of Azacoumestans via Migratory Insertion of Quinoid Carbene: Application in the Total Synthesis of Isolamellarins
  作者：Souradip Sarkar、Rajarshi Samanta

  DOI：10.1021/acs.orglett.2c01556

  日期：2022.7.1

  A weakly coordinating tert-amide-directed straightforward method was developed for the synthesis of azacoumestans using the corresponding azaheterocycle derivatives and diazonaphthoquinones under cheap Ru(II)-catalyzed conditions. The reaction proceeds via migratory insertion of quinoid carbene and subsequent Brønstead acid-mediated cyclization. The optimized C2-selective method offered a wide scope

  开发了一种弱配位叔酰胺定向的直接方法，用于在廉价的 Ru(II) 催化条件下使用相应的氮杂杂环衍生物和重氮萘醌合成氮杂香豆素。该反应通过醌型卡宾的迁移插入和随后的布朗斯特酸介导的环化进行。优化的 C2 选择性方法提供了广泛的重要氮杂杂环化合物。通过开发的方案合成了生物活性天然产物，如异醇 A 和 B。初步机制研究强调了可能的机制途径。
• Pd-Catalyzed C–H Carbonylation of (Hetero)arenes with Formates and Intramolecular Dehydrogenative Coupling: A Shortcut to Indolo[3,2-<i>c</i>]coumarins
  作者：Jie Wu、Jingbo Lan、Siyuan Guo、Jingsong You

  DOI：10.1021/ol502749b

  日期：2014.11.21

  An efficient protocol for the synthesis of (hetero)aryl carboxylic esters has been achieved by Pd-catalyzed CH carbonylation of (hetero)arenes with aryl formates. A relatively wide range of functional groups can be tolerated in this transformation, and the corresponding esters are obtained in good yields. On this basis, an intramolecular oxidative CH/CH coupling has been developed to prepare indolo[3,2-c]coumarins.
• Copper(I)-Mediated and Microwave-Assisted C_aryl−O_carboxylic Coupling:  Synthesis of Benzopyranones and Isolamellarin Alkaloids
  作者：Nopporn Thasana、Rattana Worayuthakarn、Phithakpong Kradanrat、Elliot Hohn、Lauren Young、Somsak Ruchirawat

  DOI：10.1021/jo701599g

  日期：2007.11.1

  [Graphics]A simple and highly effective C-O-carboxylic coupling reaction catalyzed by copper(l) salts has been developed to synthesize benzopyranones. The reaction of various 2-halobiarylcarboxylic acids was examined using microwave irradiation. A new class of pyrroloisoquinoline alkaloid, isolamellarin, was synthesized based on the annulation of dihydroisoquinoline with aryl pyruvates under basic condition and Cu-mediated/MW-assisted C-O-carboxylic lactonization.
• An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization
  作者：Tuanli Yao、Dawei Yue、Richard C. Larock

  DOI：10.1021/jo0517038

  日期：2005.11.1

  The iodocyclization of acetoxy-containing 2-(1-alkynyl)anisoles and subsequent direct palladium-catalyzed carbonylation/lactonization provide an efficient route to naturally occurring coumestan and coumestrol, and their related analogues.