3,3-diethyl-1-(3-ethynylphenyl)triaz-1-ene | 144001-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3-diethyl-1-(3-ethynylphenyl)triaz-1-ene
• 英文别名: 1,1-diethyl-3-(3-ethynylphenyl)triazene；3,3-diethyl-1-(3-ethynylphenyl)triazene；N-ethyl-N-[(3-ethynylphenyl)diazenyl]ethanamine
• CAS: 144001-05-8
• 化学式: C₁₂H₁₅N₃
• 分子量: 201.271
• InChiKey: ZAOJNQXAWWKNCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-diethyl-1-(3-ethynylphenyl)triaz-1-ene 在 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 1-(3-((3-((3-bromo-5-(tert-butyl)-2-((trimethylsilyl)ethynyl)phenyl)ethynyl)-5-(tert-butyl)phenyl)ethynyl)phenyl)-3,3-diethyltriaz-1-ene
  参考文献：
  名称：

  Bedard, Thomas C.; Moore, Jeffrey S., Journal of the American Chemical Society, 1995, vol. 117, # 43, p. 10662 - 10671

  摘要：

  DOI：
• 作为产物：
  描述：

  3-碘苯胺 在 盐酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 二异丙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 10.5h， 生成 3,3-diethyl-1-(3-ethynylphenyl)triaz-1-ene
  参考文献：
  名称：

  Sulfoximine Version of Double Elimination Protocol for Synthesis of Chiral Acetylenic Cyclophanes

  摘要：

  A new strategy for constructing enantiopure acetylenic cyclophanes is described on the basis of one-pot double elimination reaction starting from dialdehydes and bis(sulfoximine)s. In this case, the conventional sulfone protocol affords poorer yields of the desired cyclophanes. Thus, arylene-ethynylene moieties with terminal sulfoximine or formyl functions are linked to binaphthyl cores and these building blocks are then subjected to double elimination reaction. The desired macrocycles are obtained in up to 35% yield. The corresponding Sonogashira coupling fails to afford cyclophanes indicative of effectiveness of the double elimination methodology.

  DOI：

  10.1002/1521-3765(20020503)8:9<2005::aid-chem2005>3.0.co;2-i

文献信息

• Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source
  作者：Wanfang Li、Matthias Beller、Xiao-Feng Wu

  DOI：10.1039/c4cc03481c

  日期：——

  Gaseous sulfur dioxide was incorporated into triazenes to form various sulfonamides, catalyzed by boron trifluoride and copper chloride.

  气态二氧化硫在三氮烯中被催化剂三氟化硼和氯化铜催化形成各种磺胺类化合物。
• A Molecular Turnstile as an <i>E</i> -Field-Triggered Single-Molecule Switch: Concept and Synthesis
  作者：Loïc Le Pleux、Elisabeth Kapatsina、Julia Hildesheim、Daniel Häussinger、Marcel Mayor

  DOI：10.1002/ejoc.201700318

  日期：2017.6.16

  A new single-molecule switching concept relying on the E-field-dependent orientation of a push-pull system (via its dipole moment) is presented. As first steps towards realizing the E-field-triggered single-molecule motion, the synthesis of turnstile 1, which is designed to bridge a gap within a carbon nanotube junction, is reported. Turnstile 1 consists of a hexakis(m-phenyleneethynylene) macrocycle

  一种新的单分子开关概念依托Ë -field依赖性（通过其偶极矩）的推挽系统的取向被呈现。由于在实现第一步骤Ë -field触发单分子运动，旋转栅门的合成1，其被设计成桥接碳纳米管结内的间隙，被报告。旋转门1包括一个六（的米-phenyleneethynylene）大环饰菲官能低聚（苯撑乙炔）（OPE）在相对端处的电线，以及一对位-连接推拉杆作为旋转单元。当与周围的大环化合物的转子尺寸的相似性确保两个亚基之间的高效π堆叠ê施加-field。为了将偶极矩引入到转子中，该结构在一侧用腈基和在另一端用二甲基氨基基团进行末端官能化。基于Sonogashira-Hagihara耦合的合成协议被开发来建立大环支架。高度功能化的开放前体A是序列的关键组成部分，因为它允许进行两次分子内钯催化的环化反应，从而以68％的极高收率获得目标旋转栅。通过NMR光谱和质谱法充分表征了目标结构。此外，1 H- 1 H NOESY
• Macrocycle Embrace: Encapsulation of Fluoroarenes by<i>m</i>-Phenylene Ethynylene Host
  作者：Ilya Popov、Teng-Hao Chen、Sergey Belyakov、Olafs Daugulis、Steven E. Wheeler、Ognjen Š. Miljanić

  DOI：10.1002/chem.201406073

  日期：2015.2.9

  We report structural characterization of a new member of m‐phenylene ethynylene ring family. This shape‐persistent macrocycle also co‐crystallizes with hexafluoro‐, 1,2,4,5‐tetrafluoro‐, 1,3,5‐trifluoro, and 1,4‐difluorobenzene. The four complexes are almost isostructural, and all show the fluoroarene included into the central cavity of the macrocycle. Characterized by multiple short CH⋅⋅⋅FC contacts

  我们报告了间亚苯基亚乙炔基环家族的新成员的结构表征。这种形状持久的大环也与六氟，1,​​2,4,5-四氟，1,3,5-三氟和1,4-二氟苯共结晶。这四个复合物几乎是同构的，都显示出大环中心腔中包含的氟芳烃。由多个短C，其特征 H⋅⋅⋅F  C触点，这些包合配合物进一步二聚化在固态成2 + 2的组件，其中两个大环化合物通过由60旋转它们的大的疏水基团相互拥抱°相对于彼此。
• Geometrically-Controlled and Site-Specifically-Functionalized Phenylacetylene Macrocycles
  作者：Jinshan Zhang、Douglas J. Pesak、James L. Ludwick、Jeffrey S. Moore

  DOI：10.1021/ja00089a012

  日期：1994.5

  A convergent, stepwise synthesis of linear phenylacetylene sequences (PASs) is described. The methodology allows for complete control over chain length, sequence order of monomers, and functional group placement. Chain growth follows geometric progression thus allowing sequences of length 2(n), where n is the number of repetitive cycles, to be assembled in a total of just 3.n steps (two deprotections and one coupling for each cycle). Sequences of length other than 2(n) as well as sequences having a particular arrangement of co-monomer units, can also be realized by merging parallel repetitive cycles. Upon deprotection of the termini, these PASs can be cyclized to phenylacetylene macrocycles (PAMs) in high yield. Control over the ring structure of PAMs is determined by the chemistry of precursor PASs; the size of the macrocycle is related to the sequence length, while the geometry of the macrocycle and the position of the pendant functional groups on the macrocycle is governed by co-monomer sequence order. PAMs with four, five, six, seven, and twelve phenylacetylene monomer units, as well as a variety of site-specifically-functionalized PAMs, have been synthesized with this method. Finally, functional group transformations have been performed on some of the PAMs which lead to PAMs with new functionality. The versatile and efficient approach to this family of geometrically well-defined macrocycles offers potential for producing st set of modular building blocks to rationally assemble molecular crystals and liquid crystals. For this reason, the solid-state characteristics of the hydrocarbon skeletons are of interest. In spite of their solubility in common solvents, hydrocarbon PAMs are shown to yield crystals with remarkable thermal stability and high melting points. Three PAM hydrocarbons are shown not to exhibit melting transitions up to ca 400 degrees C, at which point an abrupt thermal irreversible reaction occurs, apparently involving a solid-state polymerization of the acetylene units.
• A tower-shaped prototypic molecule designed as an atomically sharp tip for AFM applications
  作者：Aleksey V. Rukavishnikov、Avinash Phadke、Melissa D. Lee、Donald H. LaMunyon、Pavel A. Petukhov、John F.W. Keana

  DOI：10.1016/s0040-4039(99)01207-1

  日期：1999.8

  The synthesis of macrocycle 1 using a series of Sonogashira coupling reactions is described. This tower-shaped prototypic molecule tapers to a single hydrogen atom and is designed to serve as an atomically sharp molecular tip for atomic force microscopy imaging studies. (C) 1999 Elsevier Science Ltd. All rights reserved.