1-(trimethylsilyl)-2-(3-bromo-5-tert-butylphenyl)acetylene | 144001-06-9

• 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: 1-(trimethylsilyl)-2-(3-bromo-5-tert-butylphenyl)acetylene
• 英文别名: 1-bromo-3-t-butyl-5-[(trimethylsilyl)ethynyl]benzene；2-(3-Bromo-5-tert-butylphenyl)ethynyl-trimethylsilane
• CAS: 144001-06-9
• 化学式: C₁₅H₂₁BrSi
• 分子量: 309.321
• InChiKey: SMJZBFRBNMJGCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(trimethylsilyl)-2-(3-bromo-5-tert-butylphenyl)acetylene 在 copper(l) iodide 、 Pb(dba)2 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 N-[[3-[2-(3-tert-butyl-5-ethynylphenyl)ethynyl]phenyl]diazenyl]-N-ethylethanamine
  参考文献：
  名称：

  Geometrically-Controlled and Site-Specifically-Functionalized Phenylacetylene Macrocycles

  摘要：

  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.

  DOI：

  10.1021/ja00089a012
• 作为产物：
  描述：

  4-叔丁基苯胺 在 盐酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 硫酸 、 溴 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 三乙胺 、 calcium carbonate 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 342.5h， 生成 1-(trimethylsilyl)-2-(3-bromo-5-tert-butylphenyl)acetylene
  参考文献：
  名称：

  丁二炔桥连[4的合成Ñ具有] metacyclophanes外型-annular吨丁基组

  摘要：

  通过二聚体的分子间Eglinton偶联或通过线性四聚体的分子内闭环制备具有环外叔丁基的丁二炔桥联的[4 4 ]-和[4 8 ]间环phanes 。比较[4 4 ]间环phane的1 H和13 C NMR谱与[4 8 ]环烷和二苯基丁二炔的1 H和13 C NMR谱，发现其突出的几何特征是由于三键由于线性变形而引起的。通过用硫化钠处理，以良好的产率将[4 4 ]甲基环环烷转变为[0 8 ]噻吩金属环烷。

  DOI：

  10.1016/s0040-4020(01)00779-7

文献信息

• Synthesis and self-association properties of diethynylbenzene macrocycles
  作者：Yoshito Tobe、Naoto Utsumi、Kazuya Kawabata、Koichiro Naemura

  DOI：10.1016/s0040-4039(97)82954-1

  日期：1996.12

  We synthesized diethynylbenzene macrocycles (DBMs), cyclic oligomers of diethynylbenzene, having functional groups in the periphery of the macrocyclic framework and investigated their self-association properties in solution resulting from π-π stacking interaction. The tetrakis-DBM having hexadecyl ester groups showed dimerization behavior not only in chloroform-d, but also in o-dichlorobenzene-d4.

  我们合成了二乙炔基苯的环状低聚物二乙炔基苯大环（DBMs），在大环骨架的外围具有官能团，并研究了它们在π-π堆积相互作用下在溶液中的自缔合特性。具有十六烷基酯基的四-DBM不仅在氯仿-d中，而且在邻-二氯苯-d 4中也表现出二聚作用。
• Nanoarchitectures. 1. Controlled synthesis of phenylacetylene sequences
  作者：Jinshan Zhang、Jeffrey S. Moore、Zhifu Xu、Ryan A. Aguirre

  DOI：10.1021/ja00032a060

  日期：1992.3