5,10-Dihydro-8-methoxyindeno[1,2-b]indole | 133587-46-9

• 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: 5,10-Dihydro-8-methoxyindeno[1,2-b]indole
• 英文别名: 5,10-dihydro-8-methoxyindeno<1,2-b>indole；8-Methoxy-5,10-dihydroindeno<1,2-b>indole；8-methoxy-5,10-dihydroindeno[1,2-b]indole；8-methoxy-5,10-dihydro-indeno[1,2-b]indole；5-Methoxy-indeno-<3',2':2,3>-indol
• CAS: 133587-46-9
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: AWCUTKZGHQLLKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,10-Dihydro-8-methoxyindeno[1,2-b]indole 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以66%的产率得到cis-4b,5,9b,10-tetrahydro-8-methoxyindeno<1,2-b>indole
  参考文献：
  名称：

  New antioxidants incorporating indole and indoline chromophores

  摘要：

  Syntheses of potent antioxidants utilising indenoindole or indenoindoline pharmacophores are described. The antioxidant behaviour and the oxidation potentials of these compounds are correlated, and some of their reactions with radicals are noted.

  DOI：

  10.1016/s0040-4020(01)87108-8
• 作为产物：
  描述：

  N-Indan-(1E)-ylidene-N'-(4-methoxy-phenyl)-hydrazine 在 polyphosphoric ester 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 5,10-Dihydro-8-methoxyindeno[1,2-b]indole
  参考文献：
  名称：

  New antioxidants incorporating indole and indoline chromophores

  摘要：

  Syntheses of potent antioxidants utilising indenoindole or indenoindoline pharmacophores are described. The antioxidant behaviour and the oxidation potentials of these compounds are correlated, and some of their reactions with radicals are noted.

  DOI：

  10.1016/s0040-4020(01)87108-8

文献信息

• Tetrahydroindenoindole compounds useful in the treatment of conditions
  申请人：University of Bath

  公开号：US05516788A1

  公开（公告）日：1996-05-14

  The invention concerns compounds and their enantiomers of the formula IA or IB ##STR1## and pharmaceutically acceptable salts thereof wherein each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 is independently selected from hydrogen or an alkyl group containing 1-6 carbon atoms and R.sup.5 is an alkoxy group containing 1-6 carbon atoms. The invention further concerns pharmaceutical compositions comprising the active compounds and methods employing the compounds for the treatment of conditions associated with free radical formation.

  该发明涉及化合物及其对映体，其化学式为IA或IB##STR1##及其药学上可接受的盐，其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.6、R.sup.7、R.sup.8、R.sup.9、R.sup.10、R.sup.11和R.sup.12中的每一个独立地选自氢或含有1-6个碳原子的烷基基团，而R.sup.5是含有1-6个碳原子的烷氧基团。该发明还涉及包含活性化合物的药物组合物以及利用这些化合物治疗与自由基形成相关的疾病的方法。
• One-pot-one-step, microwave-assisted Fischer indole synthesis
  作者：Evelyn Cuevas Creencia、Masayuki Tsukamoto、Takaaki Horaguchi

  DOI：10.1002/jhet.689

  日期：2011.9

  The Fischer indole synthesis was carried out using microwaves instead of conventional heating procedures. When the mixture of phenylhydrazine, cyclohexanone and zinc chloride was irradiated at 600 W for 3 min, 76% of 1,2,3,4‐tetrahydrocarbazole was obtained. However, when zinc chloride was replaced with p‐toluenesulfonic acid (p‐TSA), the reaction yielded 91% of 1,2,3,4‐tetrahydrocarbazole. Thus, a

  费歇尔吲哚合成是使用微波而不是常规加热程序进行的。当苯肼，环己酮和氯化锌的混合物在600 W的温度下照射3分钟时，得到76％的1,2,3,4-四氢咔唑。但是，当氯化锌被对甲苯磺酸（p- TSA）取代时，反应生成了91％的1,2,3,4-四氢咔唑。因此，在p- TSA催化剂存在下，用微波制备了一系列吲哚。J.杂环化​​学。（2011）。
• Synthesis of a Fluorogenic Cyclooctyne Activated by Cu-Free Click Chemistry
  作者：John C. Jewett、Carolyn R. Bertozzi

  DOI：10.1021/ol2025026

  日期：2011.11.18

  Cyclooctyne-based probes that become fluorescent upon reaction with azides are important targets for real-time imaging of azide-labeled biomolecules. The concise synthesis of a coumarin-conjugated cyclooctyne, coumBARAC, that undergoes a 10-fold enhancement in fluorescence quantum yield upon triazole formation with organic azides is reported. The design principles embodied in coumBARAC establish a platform for generating

  与叠氮化物反应后会发出荧光的基于环辛炔的探针是叠氮化物标记的生物分子实时成像的重要目标。报道了香豆素共轭环辛炔 coumBARAC 的简明合成，该化合物在与有机叠氮化物形成三唑时荧光量子产率提高了 10 倍。体现在 coumBARAC 中的设计原则建立了一个平台，用于生成适合生物成像的荧光环辛炔。
• A Tandem Oxidative Annulation Strategy for the Synthesis of Tetracyclic 3-Spirooxindole Benzofuranones
  作者：Chunxia Zhang、Min Liu、Mingruo Ding、Hao Xie、Fengzhi Zhang

  DOI：10.1021/acs.orglett.7b01374

  日期：2017.7.7

  efficient method was developed for the construction of the medicinally important tetracyclic 3-spirooxindole benzofuranones. In this highly atom- and step-economical one-pot protocol, one quaternary carbon center, two new cycles, and four new bonds (C–C/C–O/C–N) were formed under simple ligand-free copper-catalyzed conditions through a novel tandem oxidative annulation strategy.

  开发了一种简单有效的方法来构建具有医学重要性的四环3-螺氧并恶唑苯并呋喃酮。在这种高度原子和步骤经济的一锅方案中，在简单的无配体铜催化下形成了一个季碳中心，两个新环和四个新键（CC-C / C-O / C-N）通过新型串联氧化环化策略获得的条件。
• Dihydroindenoindole compounds and methods for using the same
  申请人：University of Bath

  公开号：US05185360A1

  公开（公告）日：1993-02-09

  Compounds of the formula ##STR1## wherein R is hydrogen or a lower alkyl group, R.sup.1 and R.sup.2 are independently selected from hydrogen or a lower alkyl group, R.sup.3, R.sup.4 and R.sup.6 are independently selected from hydrogen, halogen or a lower alkyl group, R.sup.5 is hydrogen, hydroxy, halogen, a lower alkyl group, a lower alkoxy group, a mono- or di-lower alkylamino group, NH.sub.2 or NR.sup.11 COR.sup.12, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are independently selected from hydrogen, hydroxy, a lower alkyl group, a lower alkoxy group, a mono- or di-lower alkylamino group, NH.sub.2 or NR.sup.11 COR.sup.12, R.sup.11 is a hydrogen or a lower alkyl group, R.sup.12 is a lower alkyl group, with the proviso that when R is hydrogen then at least one of the substituents R.sup.1 to R.sup.10 is not hydrogen, or a salt thereof, are useful as antioxidants, within the medical and non-medical field, and that when R is hydrogen, methyl or neopentyl in formula IA, then at least one of R.sup.1 to R.sup.10 is not hydrogen. Many of the compounds of formula IA and IB are new and various methods for preparing them are described.

  式为##STR1##的化合物，其中R为氢或较低烷基，R.sup.1和R.sup.2分别选择自氢或较低烷基，R.sup.3、R.sup.4和R.sup.6分别选择自氢、卤素或较低烷基，R.sup.5为氢、羟基、卤素、较低烷基、较低烷氧基、一元或二元较低烷基胺基、NH.sub.2或NR.sup.11 COR.sup.12，R.sup.7、R.sup.8、R.sup.9和R.sup.10分别选择自氢、羟基、较低烷基、较低烷氧基、一元或二元较低烷基胺基、NH.sub.2或NR.sup.11 COR.sup.12，R.sup.11为氢或较低烷基，R.sup.12为较低烷基，但当R为氢时，则至少有R.sup.1到R.sup.10中的一个取代基不为氢，或其盐，在医药和非医药领域中是有用的抗氧化剂，且当式IA中R为氢、甲基或新戊基时，则至少有R.sup.1到R.sup.10中的一个不为氢。式IA和IB的许多化合物是新的，且描述了各种制备它们的方法。