环庚三烯并[b]吲哚-10(5H)-酮,6,7,8,9-四氢- | 14961-03-6

• 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
• 中文名称: 环庚三烯并[b]吲哚-10(5H)-酮,6,7,8,9-四氢-
• 英文名称: 6,7,8,9-tetrahydrocyclohepta[b]indol-10(5H)-one
• 英文别名: 6,7,8,9-tetrahydro-5H-cyclohepta[b]indol-10-one
• CAS: 14961-03-6
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: YVBSIJXBJIQKTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  环庚三烯并[b]吲哚-10(5H)-酮,6,7,8,9-四氢- 以89%的产率得到
  参考文献：
  名称：

  YAMANE K.; FUJIMORI K., BULL. CHEM. SOC. JAP. , 1976, 49, NO 4, 1101-1104

  摘要：

  DOI：
• 作为产物：
  描述：

  2-iodocyclohept-2-en-1-one 在 bis-triphenylphosphine-palladium(II) chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 1,10-菲罗啉 、 三苯胂 、 一氧化碳 、 1,3-双(二苯基膦)丙烷 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、607.95 kPa 条件下， 生成 环庚三烯并[b]吲哚-10(5H)-酮,6,7,8,9-四氢-
  参考文献：
  名称：

  Novel palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones

  摘要：

  Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to carbazolones, an intermolecular Stille coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation. A number of functionalized 1,2-dihydro-4(3H)-carbazolones were prepared using this sequence. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00072-2

文献信息

• [EN] FUSED POLYCYCLIC 2-PYRIDINONE ANTIBACTERIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS DE 2-PYRIDINONE POLYCYCLIQUE
  申请人：PTC THERAPEUTICS INC

  公开号：WO2016109706A1

  公开（公告）日：2016-07-07

  The present description relates to fused polycyclic 2-pyridinone compounds and forms and pharmaceutical compositions thereof and methods of using such compounds, forms or compositions thereof for treating or ameliorating a wild-type or drug-resistant form of N. gonorrhoeae or N. meningitides. A compound of Formula (la), Formula (lb) or Formula (Ic), or a form thereof, wherein the dashed lines represent one or more double bonds optionally present where allowed by available valences.

  本描述涉及融合的多环2-吡啶酮化合物及其形式和药物组合物，以及使用这些化合物、形式或组合物治疗或改善N. gonorrhoeae或N. meningitides的野生型或耐药型的方法。其中，化合物的化学式为（la）、（lb）或（Ic），或其形式，其中虚线代表一个或多个双键，根据可用的价键允许的情况下可选择地存在。
• Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction
  作者：Tezcan Guney、Todd A. Wenderski、Matthew W. Boudreau、Derek S. Tan

  DOI：10.1002/chem.201802880

  日期：2018.9.6

  Medium‐ring natural products exhibit diverse biological activities but such scaffolds are underrepresented in probe and drug discovery efforts due to the limitations of classical macrocyclization reactions. We report herein a tandem oxidative dearomatization‐ring‐expanding rearomatization (ODRE) reaction that generates benzannulated medium‐ring lactams directly from simple bicyclic substrates. The

  中环天然产物表现出多种生物活性，但由于经典大环化反应的局限性，此类支架在探针和药物发现工作中代表性不足。我们在此报告了一种串联氧化脱芳构化-扩环重芳构化（ODRE）反应，该反应直接从简单的双环底物生成苯并环中环内酰胺。该反应可容纳多种芳基底物（卤代芳烃、芳基醚、芳基酰胺、杂环），并且桥头醇的策略性掺入可在产品中生成适合下游修饰的多功能酮部分。化学信息学分析表明，这些中等环进入与相关天然产物重叠且不同于合成药物的化学空间区域，为它们用于针对新生物靶标的发现筛选奠定了基础。
• New imidazolylmethyl-cycloalkane(b)indolones
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0338650A1

  公开（公告）日：1989-10-25

  The invention relates to new imidazolylmethyl-cycloalka­ne[b]indolones having formula wherein - R₀ is alkyl or alkoxy having 1-4 C-atoms, hydroxy, halogen, trifluoromethyl, a group R₆R₇N or R₆R₇-N-CO, wherein R₆ and R₇ are hydrogen or alkyl having 1-4 C-­atoms or wherein R₆R₇N is a saturated 5-6 ring and n has the value 0, 1 or 2, - R₁ is hydrogen, 1-8 C alkyl, 3-7 C cycloalkyl, 3-7 C cycloalkyl-(1-3 C)- alkyl, 3-6 C alkenyl, 3-8 C alkynyl, phenyl or phenyl-(1-3 C) alkyl, wherein the phenyl group may be substituted with one or more alkyl groups, alkoxy groups or OH-groups or with one or more halogen atoms, or R₁ is a group COOR₈, COR₈, SO₂R₈, wherein R₈ is 1-4 C alkyl, 3-7 C cycloalkyl, phenyl or phenyl-(1-2 C)alkyl wherein the phenyl group may be substituted with one or more 1-4 C alkyl groups, 1-4 C alkoxy groups, hydroxyl groups or halogen atoms, or R₁ is a group R₉R₁₀N-C ⁰ wherein R₉ and R₁₀ independently of each other are hydrogen, 1-4 C alkyl, phenyl or phenyl-(1-2 C)alkyl wherein the phenyl group may be substituted, or wherein R₉ and R₁₀ together with the nitrogen atom to which they are bound constitute a saturated 5-6 ring, - one of the groups R₂, R₃ and R₄ is hydrogen, alkyl having 1-4 C atoms, cycloalkyl having 3-6 C-atoms, alkenyl having 2-4 C-atoms or phenyl-alkyl having 1-2 C-atoms in the alkyl group and the two other groups, independently of each other, are hydrogen or alkyl having 1-4 C-atoms, - m has the value 3 to 8 inclusive, and the pharmaceutically acceptable acid addition salts thereof. The compounds have a longer-lasting selective anta­gonistic activity on "neuronal" 5-hydroxytryptamine (5-HT) receptors as compared with related known compounds, and they are less toxic.

  该发明涉及新的咪唑基甲基-环烷[b]吲哚酮类化合物，其化学式为：其中，- R₀是具有1-4个碳原子的烷基或烷氧基，羟基，卤素，三氟甲基，R₆R₇N或R₆R₇-N-CO基团，其中R₆和R₇是氢或具有1-4个碳原子的烷基，或者R₆R₇N是饱和的5-6环，n的值为0，1或2，- R₁是氢，1-8个碳原子的烷基，3-7个碳原子的环烷基，3-7个碳原子的环烷基-(1-3个碳原子)-烷基，3-6个碳原子的烯基，3-8个碳原子的炔基，苯基或苯基-(1-3个碳原子)烷基，其中苯基可以被一个或多个烷基，烷氧基或羟基取代，或者被一个或多个卤素原子取代，或者R₁是COOR₈，COR₈，SO₂R₈基团，其中R₈是1-4个碳原子的烷基，3-7个碳原子的环烷基，苯基或苯基-(1-2个碳原子)烷基，其中苯基可以被一个或多个1-4个碳原子的烷基，1-4个碳原子的烷氧基，羟基或卤素原子取代，或者R₁是R₉R₁₀N-C ⁰基团，其中R₉和R₁₀彼此独立地是氢，1-4个碳原子的烷基，苯基或苯基-(1-2个碳原子)烷基，其中苯基可以被取代，或者R₉和R₁₀连同它们所结合的氮原子构成饱和的5-6环，- R₂，R₃和R₄中的一个是氢，具有1-4个碳原子的烷基，具有3-6个碳原子的环烷基，具有2-4个碳原子的烯基或具有1-2个碳原子的苯基-烷基，而另外两个基团独立地是氢或具有1-4个碳原子的烷基，- m的值为3到8，包括8，并且其药学上可接受的酸盐。这些化合物与相关已知化合物相比具有更持久的选择性拮抗“神经元”5-羟色胺（5-HT）受体的活性，并且毒性更低。
• Nitrene C−H Bond Insertion Approach to Carbazolones and Indolones, and a Reactivity Departure for 7‐Membered Analogues**
  作者：Mahesh K. Lakshman、Dellamol Sebastian、Padmanava Pradhan、Michelle C. Neary、Alexis M. Piette、Samuel P. Trzebiatowski、Alexander E. K. Henriques、Patrick H. Willoughby

  DOI：10.1002/chem.202302995

  日期：2023.12.22

  2-Arylcyclohexane-1,3-diones and 2-arylcyclopentane-1,3-diones can be converted in a facile 2-step, 1-pot manner to 2-aryl-3-azidocycloalk-2-en-1-ones. These azides can be smoothly cyclized to carbazolones and indolones with catalytic Rh2(O2CC7H15)4. Although 3-azido-2-phenylcyclohept-2-en-1-one could be readily prepared from 2-phenylcycloheptane-1,3-dione, by contrast the Rh-catalyzed cyclization

  2-芳基环己烷-1,3-二酮和2-芳基环戊烷-1,3-二酮可以通过简单的两步、一锅法转化为2-芳基-3-叠氮基环烷-2-en-1-酮。这些叠氮化物可以在催化Rh 2 (O 2 CC 7 H 15 ) 4的作用下顺利环化为咔唑酮和吲哚酮。虽然 3-叠氮基-2-苯基环庚-2-en-1-酮可以很容易地从 2-苯基环庚烷-1,3-二酮制备，但相比之下，Rh 催化的环化反应优先于吲哚生成氮丙啶。机理和 DFT 研究补充了综合工作。
• Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels–Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones
  作者：Hyung-Seok Yoo、Jeong-Won Shin、Yoon Hu Jang、Yo-Sep Yang、Seung Hwan Son、Hyuck-Jae Won、Soo Lim Kim、Jaehoon Sim、Nam-Jung Kim

  DOI：10.1021/acs.joc.3c02558

  日期：2024.3.1

  An approach to 2,3-benzotropone from 1-benzosuberone via palladium(II)-catalyzed aerobic dehydrogenation was developed. This method first provided a catalytic route to various 2,3-benzotropones from their corresponding 1-benzosuberones in good yields. In addition, the reaction could be applied to a one-pot Diels–Alder reaction with maleimide, providing a complex benzobicyclo[3.2.2]nonenone in ≤90%

  开发了一种通过钯 (II) 催化有氧脱氢从 1-苯并环庚酮生产 2,3-苯并托酮的方法。该方法首先提供了从相应的 1-苯并环庚酮制备各种 2,3-苯并环酮的催化路线，且产率良好。此外，该反应可应用于与马来酰亚胺的一锅狄尔斯-阿尔德反应，以≤90%的产率提供复杂的苯并双环[3.2.2]壬烯酮。还进行了支持我们提出的机制的动力学分析，强调了所开发的合成途径的稳健性。