1,2,3,4-tetrafluoro-5,8-dihydro-5,8-N-methylaminonaphthalene | 5875-75-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,3,4-tetrafluoro-5,8-dihydro-5,8-N-methylaminonaphthalene
• 英文别名: 9-methyl-5,6,7,8-tetrafluoro-1,4-dihydronaphthalen-1,4-imine；N-methyl-5,6,7,8-tetrafluoro-1,4-dihydro-1,4-iminonaphtalene；9-methyl-9-aza-5,6,7,8-tetrafluorobenzonorbornadiene；5,6,7,8-tetrafluoro-9-methyl-1,4-dihydro-1,4-epiazano-naphthalene；1,2,3,4-Tetrafluor-5,8-dihydro-5,8-(N-methylimino)-naphthalin；9-Methyl-5,6,7,8-tetrafluoro-1,4-dihydronaphthalin-1,6-imin；9-Methyl-5,6,7,8-tetrafluoro-1,4-dihydronaphthalen-l,4-imine；3,4,5,6-tetrafluoro-11-methyl-11-azatricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraene
• CAS: 5875-75-2；145920-67-8
• 化学式: C₁₁H₇F₄N
• 分子量: 229.177
• InChiKey: SAWOGBAOSZAGLW-UHFFFAOYSA-N

物化性质

• 熔点：
  74.5-76.0 °C(Solv: hexane (110-54-3))
• 沸点：
  80 °C(Press: 0.5 Torr)
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrafluoro-5,8-dihydro-5,8-N-methylaminonaphthalene 在 sodium hydroxide 、 氯仿 、 苄基三乙基氯化铵 作用下， 以85%的产率得到1,2,3,4-四氟萘
  参考文献：
  名称：

  Dichlorocarbene-induced deamination of naphthalen-1,4-imines and anthracen-9,10-imines

  摘要：

  DOI：

  10.1021/jo00318a039
• 作为产物：
  描述：

  5,6,7,8-Tetrafluor-1,4-dihydronaphthalin-1,4-imin 以75%的产率得到
  参考文献：
  名称：

  ANDERSON P. S.; CHRISTY M. E.; LUNDELL G. F.; PONTICELLI G. S., TETRAHEDRON LETT. , 1975, NO 30, 2553-2556

  摘要：

  DOI：

文献信息

• Universal building blocks and support media for synthesis of oligonucleotides and their analogs
  申请人：——

  公开号：US20040152905A1

  公开（公告）日：2004-08-05

  Compounds for the synthesis of oligomeric compounds, particularly oligonucleotides and chemically modified oligonucleotide analogs, are provided. In addition, methods for functionalization of a support medium with a first monomeric subunit and methods for the synthesis of oligomeric compounds utilizing the novel compounds bound to support media are provided.

  提供用于合成寡聚化合物，特别是寡核苷酸和化学修饰的寡核苷酸类似物的化合物。此外，还提供了将支持介质功能化为第一单体亚基的方法，以及利用与支持介质结合的新化合物合成寡聚化合物的方法。
• Preparation and spectroscopic studies of the 1,4-dihydro- 1,4-iminonaphthalene (7-azabenzonorbornadiene) ring system
  作者：John W. Davies、Michael L. Durrant、Matthew P. Walker、Djaballah Belkacemi、John R. Malpass

  DOI：10.1016/s0040-4020(01)88190-4

  日期：——

  (7-azabenzonorbornadienes) and reduced derivatives is described together with 1,4-dihydro-1,4- and 9,10-dihydro-9,10- iminoanthracenes. VT NMR studies lead to unambiguous assignment of invertomer preferences; changes in the invertomer ratios and nitrogen inversion barriers are investigated as the electronic and steric environment is modified by variation of substituents in the carbon skeleton and at nitrogen

  描述了一系列N-烷基1,4-二氢-1,4-亚氨基萘（7-氮杂苯并降冰片二烯）和还原衍生物与1,4-二氢-1,4-和9,10-二氢-9的合成，10-亚氨基蒽。VT NMR研究可明确确定内向异构体的偏好。随着碳骨架中和氮原子上取代基的变化而改变了电子和空间环境，研究了转化体比率和氮转化障碍的变化。
• Synthesis and Nonlinear Optical Properties of Fluorine-Containing Naphthalocyanines
  作者：Guo Ying Yang、Michael Hanack、Yiew Wang Lee、Yu Chen、May Ka Yuen Lee、Danilo Dini

  DOI：10.1002/chem.200204683

  日期：2003.6.16

  The fluorine-containing metal naphthalocyanines [F16NcGaCl] (7) and [(F16NcGa)2O] (8), which represent the first examples of peripherally fluorine substituted naphthalocyanines, were synthesized, and the nonlinear optical transmission was studied. Peripheral substitution by fluorine atoms enhances the solubility and photostability of the naphthalocyanines. In particular, for the axially mu-oxo-bridged

  合成了代表周边被氟取代的萘菁的第一实例的含氟金属萘菁[F16NcGaCl]（7）和[（F16NcGa）2O]（8），并研究了非线性光学透射率。氟原子的周边取代增强了萘酞菁的溶解度和光稳定性。特别是，对于轴向多氧桥联萘酞菁二聚体8，在有机溶剂中几乎没有观察到聚集，并且当用波长为532 nm的激光脉冲照射时，它是有效的光学限制剂，脉冲持续时间为5 ns和20 Hz的重复频率。
• Synthesis of Benzonorbornadienes:  Regioselective Benzyne Formation
  作者：Kenneth C. Caster、Christopher G. Keck、Russell D. Walls

  DOI：10.1021/jo001277k

  日期：2001.5.1

  of cyclopentadiene derivatives with substituted benzyne intermediates, which were generated by low-temperature metal--halogen exchange of halobenzenes. General conditions were developed, allowing synthesis of most benzonorbornadienes described herein at the multigram scale with isolated yields approaching 90% in some cases. Cycloaddition of the benzyne produced by substitution of a chlorodifluorobenzene

  该报告详细介绍了通过Diels-Alder环戊二烯衍生物与取代的苯炔中间体的加成反应合成几种苯并降冰片二烯的方法，这些取代苯是由卤代苯的低温金属-卤素交换产生的。开发了一般条件，使得可以在数克规模上合成本文所述的大多数苯并降冰片二烯，在某些情况下分离产率接近90％。在金属-卤素交换反应中，用氯代二氟苯取代溴代二氟苯生成的苯环的环加成反应出乎意料地得到了不同的苯并降冰片二烯。由去质子化途径而不是由金属-卤素交换产生的苯炔在高度区域选择性消除步骤中形成。
• 15N nuclear magnetic resonance studies of azabicycles; unusual deshielding of nitrogen in the 7-azabicyclo[2.2.1]heptyl ring system
  作者：Djballah Belkacemi、John W Davies、John R Malpass、Antoinette Naylor (née Bathgate)、Craig R Smith

  DOI：10.1016/s0040-4020(01)89045-1

  日期：——

  samples of derivatives of the 7-azabicyclo[2.2.1]heptyl system were synthesised and 15N NMR spectra were recorded using 15N-enriched and natural abundance samples; separate signals were observed for the two invertomers in N-methyl and N-chloro derivatives. Considerable deshielding was observed in comparison with simple amines and with 8-azabicyclo[3.2.1]octyl and 9-azabicyclo[4.2.1]nonyl analogues.

  15的N-富集的7-氮杂双环[2.2.1]庚基系统的衍生物的样品的合成和15使用N个记录NMR谱15的N-富集的和天然丰度的样品; 在N-甲基和N-氯代衍生物中观察到两个反相子的单独信号。与简单的胺以及8-氮杂双环[3.2.1]辛基和9-氮杂双环[4.2.1]壬基类似物相比，观察到相当大的脱屏蔽。化学位移的可预测变化是由于在氮和α-碳处的取代引起的；还研究了在氮原子上的构型，不饱和度以及进一步取代氮原子的影响。