8,9,10,11-tetrahydro-7H-cyclohepta[c]quinoline | 6574-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8,9,10,11-tetrahydro-7H-cyclohepta[c]quinoline
• 英文别名: 8,9,10,11-tetrahydro-7H-cyclohepta[c]quinoline；8,9,10,11-Tetrahydro-7H-cyclohepta[c]chinolin；8,9,10,11-Tetrahydro-7H-cycloheptachinolin
• CAS: 6574-88-5
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: COYMTXUGSYPJTM-UHFFFAOYSA-N

物化性质

• 熔点：
  65-67 °C
• 沸点：
  349.9±11.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴环庚烯-1-甲醛 在 palladium on activated charcoal 、 tris(dibenzylideneacetone)dipalladium (0) 氢气 、 铜 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 18.0~80.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 8,9,10,11-tetrahydro-7H-cyclohepta[c]quinoline
  参考文献：
  名称：

  Synthesis of Quinolines, 2-Quinolones, Phenanthridines, and 6(5H)-Phenanthridinones via Palladium[0]-Mediated Ullmann Cross-Coupling of 1-Bromo-2-nitroarenes with β-Halo-enals, -enones, or -esters

  摘要：

  Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of beta-halo-enals, -enones, or -esters readily affords the corresponding beta-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl3 in aqueous acetone.

  DOI：

  10.1021/ol0490375
• 作为试剂：
  描述：

  (S)-2-phthalimido-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)propanamide 、 (2-甲氧基苯基)三乙氧基硅烷 在 palladium diacetate 、 silver fluoride 、 8,9,10,11-tetrahydro-7H-cyclohepta[c]quinoline 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以67%的产率得到(S)-3-(2-methoxyphenyl)-2-phthalimido-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)propanamide
  参考文献：
  名称：

  Ligand-Enabled Cross-Coupling of C(sp³)–H Bonds with Arylsilanes

  摘要：

  Pd(II)-catalyzed cross-coupling of C(sp(3))-H bonds with organosilicon coupling partners has been achieved for the first time. The use of a newly developed quinoline-based ligand is essential for the cross-coupling reactions to proceed.

  DOI：

  10.1021/jacs.5b00890

文献信息

• Cascade C-C and C-N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinol­ines
  作者：Ashwini Borah、Pranjal Gogoi

  DOI：10.1002/ejoc.201600220

  日期：2016.4

  Pd-catalyzed cascade process has been developed for the synthesis of quinoline and phenanthridine derivatives from various β-chloro α,β-unsaturated aldehydes and 2-chloroaryl aldehydes, respectively, in good to high yields. The reaction proceeds through Pd-catalyzed cascade carbon–carbon and carbon–nitrogen bond formation in a single reaction vessel. The requisite β-chloro α,β-unsaturated aldehydes were efficiently

  已经开发了一种 Pd 催化的级联工艺，用于分别从各种 β-氯 α,β-不饱和醛和 2-氯芳基醛合成喹啉和菲啶衍生物，收率良好。该反应通过 Pd 催化的级联碳 - 碳和碳 - 氮键在单个反应容器中形成。必需的β-氯α,β-不饱和醛是由相应的羰基化合物有效合成的。配体 Sphos 与 Pd(OAc)2 的使用对于本级联工艺的成功实施至关重要。该合成方案也适用于三球定生物碱的克级合成。
• Substituted 1,10-Phenanthrolines. IX. Cycloalkeno Derivatives¹
  作者：FRANCIS H. CASE

  DOI：10.1021/jo01116a005

  日期：1956.10
• New protocols for the synthesis of 3,4-annulated and 4-substituted quinolines from β-bromo-α,β-unsaturated aldehydes and 1-bromo-2-nitrobenzene or 2-bromoacetanilide
  作者：Surajit Some、Jayanta K. Ray、Martin G. Banwell、Matthew T. Jones

  DOI：10.1016/j.tetlet.2007.03.078

  日期：2007.5

  The palladium[0]-mediated Ullmann cross-coupling of readily available beta-bromo-alpha,beta-unsaturated aldehydes of the general form 2 with 1-bromo-2-nitrobenzene (3, X = Br) delivers products, 4, that undergo reductive cyclization to novel quinolines (5) upon exposure to indium in aqueous ammonium chloride or to Raney-nickel in the presence of dihydrogen. Analogous cross-coupling of 2-bromoacetanilide (6) with 2 affords products of type 7 that undergo in situ and K2CO3-mediated cyclization to give the same types of quinolines (5). (C) 2007 Elsevier Ltd. All rights reserved.