7,8-Dihydrobenzophenanthridine | 63682-86-0

• 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: 7,8-Dihydrobenzophenanthridine
• 英文别名: 7,8-dihydrobenzo[k]phenanthridine；Benzophenanthridine；7,8-dihydro-benzo[k]phenanthridine；7,8-Dihydrobenzophenanthridin
• CAS: 63682-86-0
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: MBHZHSKXZYGYNF-UHFFFAOYSA-N

物化性质

• 沸点：
  419.6±14.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-溴-2-硝基苯 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 7,8-Dihydrobenzophenanthridine
  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

文献信息

• Preparation of 1-substituted-3,4-dihydronaphthalene-2-carboxaldehyde N,N-dimethylhydrazones by palladium(0) coupling, and their electrocyclic ring closure
  作者：Thomas L. Gilchrist、Maureen A.M. Healy

  DOI：10.1016/s0040-4020(01)86333-x

  日期：1993.3

  involving halogen-metal exchange and palladium(0) catalysed cross coupling, into N,N-dimethylhydrazones of 1-aryl- and 1-vinyl-3,4-dihydronaphthalene-2- carboxaldehydes. The N,N-dimethylhydrazone 10 of the aldehyde 2 undergoes efficient bromine-lithium exchange with butyllithium, as does 2-bromobenzaldehyde N,N-dimethylhydrazone 17. The dimethylhydrazones of 1-vinyl-3,4-dihydronaphthalene-2-carboxaldehydes

  1-溴-3,4-二氢萘-2-甲醛2已通过三种方法转化，分别涉及卤素-金属交换和钯（0）催化的交叉偶联，转化为1-芳基和1-的N，N-二甲基hydr乙烯基-3,4-二氢萘-2-甲醛。的N，N- -dimethylhydrazone 10醛的2所与丁基锂经历高效溴-锂交换，象2-溴苯甲醛-N，N- -dimethylhydrazone 17。的1-乙烯基-3,4-二氢化萘-2-羧醛的dimethylhydrazones不是由后行电环环闭合，随后在溶液中二甲胺的损失，得到5,6-二氢苯并〔分离˚F]异喹啉。当进行气相热解时， 1-芳基-3，4-二氢萘-2-羧醛N，N-二甲基hydr也以相同的方式环化。
• 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。
• Synthesis of fused pyridines by electrocyclic ring closure of aldehyde NN-dimethylhydrazones
  作者：Thomas L. Gilchrist、Maureen A.M. Healy

  DOI：10.1016/s0040-4039(00)97965-6

  日期：1990.1

  3,4-Dihydronaphthalene-2-carboxaldehyde NN-dimethydrazone bearing an alkenyl or aryl substituent at the 1-position undergo thermal electrocyclic ring closure followed by the loss of dimethylamine, giving fused pyridines.

  在1-位带有烯基或芳基取代基的3,4-二氢萘-2-甲醛NN-二met经历热电环闭合，然后损失二甲胺，得到稠合的吡啶。
• Synthesis of Quinolines, 2-Quinolones, Phenanthridines, and 6(5<i>H</i>)-Phenanthridinones via Palladium[0]-Mediated Ullmann Cross-Coupling of 1-Bromo-2-nitroarenes with β-Halo-enals, -enones, or -esters
  作者：Martin G. Banwell、David W. Lupton、Xinghua Ma、Jens Renner、Magne O. Sydnes

  DOI：10.1021/ol0490375

  日期：2004.8.1

  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.
• GILCHRIST, THOMAS L.;HEALY, MAUREEN A. M., TETRAHEDRON LETT., 31,(1990) N0, C. 5807-5810
  作者：GILCHRIST, THOMAS L.、HEALY, MAUREEN A. M.

  DOI：——

  日期：——