12-(1H-indol-3-yl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one | 1171121-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 12-(1H-indol-3-yl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• 英文别名: 12-(1H-indol-3-yl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one；9,10-dihydro-12-(1H-indol-3-yl)-9,9-dimethyl-8H-benzo[a]xanthen-11(12H)-one；12-(1H-indol-3-yl)-9,9-dimethyl-8,9,10,12-tetrahydro-11H- benzo[a]xanthen-11-one；12-(indol-3-yl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one；12-(1H-indol-3-yl)-9,9-dimethyl-10,12-dihydro-8H-benzo[a]xanthen-11-one
• CAS: 1171121-17-7
• 化学式: C₂₇H₂₃NO₂
• 分子量: 393.485
• InChiKey: VMUCEMQMGOMEOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-萘酚 在 甲酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 生成 12-(1H-indol-3-yl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  获取功能化 4H-色烯的新合成方法

  摘要：

  使用类苯胺化合物与 1,3-二酮和吲哚的多组分多米诺偶联反应，开发了一种简单、高效和高产的单锅法，用于合成新型官能化 4H-色烯和色烯羧酸。在无溶剂条件下存在甲酸催化剂。该协议避免使用昂贵的催化剂、有毒溶剂和色谱分离。

  DOI：

  10.3184/174751916x14792153319761

文献信息

• An efficient solvent free multicomponent synthesis of functionalized 4H-chromenes by using reusable, heterogeneous Amberlite IRA-400 Cl resin as catalyst
  作者：Gurusamy Harichandran、Parkunan Parameswari、Madasamy Kanagaraj、Ponnusamy Shanmugam

  DOI：10.1016/j.tetlet.2014.11.043

  日期：2015.1

  A simple and efficient Amberlite IRA-400 Cl resin catalyzed multicomponent reaction of 2-hydroxy-1-naphthaldehyde, 1,3-diketone, and nucleophile under solvent free condition to obtain the biological important 4H-chromene derivatives has been outlined. Significant features of this method are the simplicity of the procedure, the ready accessibility, and cost effectiveness of the catalyst, and higher yields

  概述了一种简单有效的Amberlite IRA-400 Cl树脂在无溶剂条件下催化2-羟基-1-萘醛，1,3-二酮和亲核试剂的多组分反应，以获得生物学上重要的4H-色烯衍生物的方法。该方法的重要特征是该方法的简单性，催化剂的容易获得性和成本效益以及在相对较短的反应时间内获得较高的收率。由单晶X射线研究证实了化合物4j和5c的结构。
• An Organocatalyzed Expeditious Synthetic Route to Tetrahydrobenzo[a]xanthen-11-ones via Grinding Technique
  作者：Pravin V. Shinde、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.2174/157017811797249308

  日期：2011.10.1

  In the present study, successful implementation of grinding technique and camphor sulphonic acid (CSA) as a catalyst, has been demonstrated for the rapid synthesis of 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11- ones at ambient temperatures, avoiding excessive/wasteful heating.

  在本研究中，成功实施了研磨技术和樟脑磺酸（CSA）作为催化剂，证明可以在常温下快速合成12-芳基-9,9-二甲基-8,9,10,12-四氢苯并[a]黄烷-11-酮，避免了过度/浪费的加热。
• Surfactant catalyzed convenient and greener synthesis of tetrahydrobenzo[<i>a</i>]xanthene-11-ones at ambient temperature
  作者：Pravin V Shinde、Amol H Kategaonkar、Bapurao B Shingate、Murlidhar S Shingare

  DOI：10.3762/bjoc.7.9

  日期：——

  An efficient and greener protocol for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one using tetradecyltrimethylammonium bromide (TTAB) at room temperature in water is described.

  描述了一种在水中使用溴化十四烷基三甲基铵（TTAB）在室温下合成12-芳基-8,9,10,12-四氢苯并[a]苯并吖啶酮的高效且更环保的方法。
• A Simple and Green Approach for the Synthesis of Tetrahydrobenzo[a]-xanthen-11-one Derivatives Using Tetrabutyl Ammonium Fluoride in Water
  作者：Ching-Fa Yao、Shijay Gao、Chen Tsai

  DOI：10.1055/s-0028-1088214

  日期：2009.4

  An efficient and simple procedure for the synthesis of 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives has been described. This one-pot multicomponent reaction involves the reaction of aldehydes, 2-naphthol, and cyclic 1,3-diketones in the presence of catalytic amount of recyclable TBAF in water.

  已描述一种高效简单的合成12-芳基或12-烷基-8,9,10,12-四氢苯并[a]荧蒽-11-酮衍生物的程序。这种“一锅法”多组分反应涉及在可回收的催化剂TBAF（四丁基氟化铵）存在下，用水作为溶剂，反应醛、2-萘酚和环状1,3-二酮。
• An organocatalyst from renewable materials for the synthesis of coumarins and chromenes: three-component reaction and multigram scale synthesis
  作者：Rapeepat Sangsuwan、Sasithorn Sangher、Thammarat Aree、Chulabhorn Mahidol、Somsak Ruchirawat、Prasat Kittakoop

  DOI：10.1039/c4ra00673a

  日期：——

  A new concept of catalysts which are prepared from renewable materials is demonstrated for the synthesis of coumarins and chromenes.

  展示了一种利用可再生材料制备的催化剂的新概念，用于合成香豆素和咖啡因。