1-bromo-4-(trimethysilyl)-2,5-dimethoxybenzene | 217456-82-1

• 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-bromo-4-(trimethysilyl)-2,5-dimethoxybenzene
• 英文别名: 1-bromo-2,5-dimethoxy-4-(trimethylsilyl)benzene；(4-Bromo-2,5-dimethoxyphenyl)trimethylsilane；(4-bromo-2,5-dimethoxyphenyl)-trimethylsilane
• CAS: 217456-82-1
• 化学式: C₁₁H₁₇BrO₂Si
• 分子量: 289.244
• InChiKey: RSTOMVISQQNKHG-UHFFFAOYSA-N

物化性质

• 沸点：
  295.8±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromo-4-(trimethysilyl)-2,5-dimethoxybenzene 在 四(三苯基膦)钯 、 一氯化碘 、 三溴化硼 、 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 126.0h， 生成 4'''-Iodo-4,2',5'-tris-[3-(2-methoxy-ethoxy)-2-(2-methoxy-ethoxymethyl)-propoxy]-[1,4';1',1'';4'',1''']quaterphenyl
  参考文献：
  名称：

  Self-Assembling Molecular Trees Containing Octa-p-phenylene:  From Nanocrystals to Nanocapsules

  摘要：

  Tree-shaped molecules consisting of octa-p-phenylene as a stem segment and oligoether dendrons as a flexible head were synthesized and characterized. The molecular tree based on a small flexible head self-assembles into a lamellar structure, whereas the molecule based on a larger headgroup self-assembles into a discrete heptameric bundle that organizes into a 3-D primitive orthorhombic supercrystals, as confirmed by X-ray scatterings and transmission electron microscopic (TEM) observations. Optical studies revealed that the absorption and emission maxima and absorption edge of the 3-D structure shift to higher energy compared to those of the lamellar structure. The molecules in dilute solution (THF/ water = 1:10 v/v) were observed to self-assemble into capsule-like hollow aggregates, as confirmed by dynamic and static light scatterings, scanning electron microscopy (SEM), and TEM investigations. These results demonstrate that tree-shaped molecules are capable of packing into organized discrete nanocrystals with parallel arrangement as well as hollow nanocapsules with radial arrangement, depending on the presence of selective solvents for flexible headgroup.

  DOI：

  10.1021/ja048856h
• 作为产物：
  描述：

  三甲基氯硅烷 、 1,4-二溴-2,5-二甲氧基苯 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以80%的产率得到1-bromo-4-(trimethysilyl)-2,5-dimethoxybenzene
  参考文献：
  名称：

  Self-Assembling Molecular Trees Containing Octa-p-phenylene:  From Nanocrystals to Nanocapsules

  摘要：

  Tree-shaped molecules consisting of octa-p-phenylene as a stem segment and oligoether dendrons as a flexible head were synthesized and characterized. The molecular tree based on a small flexible head self-assembles into a lamellar structure, whereas the molecule based on a larger headgroup self-assembles into a discrete heptameric bundle that organizes into a 3-D primitive orthorhombic supercrystals, as confirmed by X-ray scatterings and transmission electron microscopic (TEM) observations. Optical studies revealed that the absorption and emission maxima and absorption edge of the 3-D structure shift to higher energy compared to those of the lamellar structure. The molecules in dilute solution (THF/ water = 1:10 v/v) were observed to self-assemble into capsule-like hollow aggregates, as confirmed by dynamic and static light scatterings, scanning electron microscopy (SEM), and TEM investigations. These results demonstrate that tree-shaped molecules are capable of packing into organized discrete nanocrystals with parallel arrangement as well as hollow nanocapsules with radial arrangement, depending on the presence of selective solvents for flexible headgroup.

  DOI：

  10.1021/ja048856h

文献信息

• Synthesis of the Tetracyclic Carbon Core of Menogaril Utilizing the Benzannulation Reaction of a Fischer Carbene Complex and an Alkyne
  作者：Jing Su、William D. Wulff、Richard G. Ball

  DOI：10.1021/jo981481w

  日期：1998.11.1

  The synthesis of the 2-bromoanthracyclinone 3 containing the tetracyclic core of menogaril is achieved with a strategy that is formulated around the benzannulation reaction of a Fischer carbene complex and an alkyne. This benzannulation requires a 2,5-dimethoxyphenyl carbene complex that bears an additional functional group at the 4-position that is the nascent 2-bromo substituent in 3. The evaluation of 4-bromo- and 4-trimethysilyl-substituted complexes with 1-pentyne revealed that the benzannulation was more efficient with the silyl complex. The synthesis of 3 is achieved with methoxy and acetoxy substituents at the C-9 position, which begins with the methoxy- and benzyloxy-substituted alkynes 14 and 30 that contain the A ring of the menogaril core. The closure of the last ring is accomplished by a Friedel-Crafts reaction on an in situ generated acid chloride. Adjustment of the oxidation states of the B and C rings failed according to procedures that had been developed in model studies. This was accomplished in an unexpected fashion with novel bromination reactions that occurred at a benzylic position with the C-9 methoxyl derivative and alpha to a ketone in the C-9 acetoxy derivative.
• Helical Nanofibers from Aqueous Self-Assembly of an Oligo(<i>p</i>-phenylene)-Based Molecular Dumbbell
  作者：Jinyoung Bae、Jin-Ho Choi、Yong-Sik Yoo、Nam-Keun Oh、Byung-Sun Kim、Myongsoo Lee

  DOI：10.1021/ja051961m

  日期：2005.7.13

  We have synthesized an amphiphilic dumbbell-shaped molecule consisting of dodeca-p-phenylene and aliphatic polyether dendrons as flexible end groups. The molecular dumbbell in aqueous solution self-assembles into well-defined left-handed helical cylinders with a diameter (8 nm) of a molecular length scale and a pitch length of 5.6 nm, as confirmed by TEM. These elementary helical fibrils are further assembled to give left-handed superhelical fibers with lengths up to several micrometers. Such a well-defined helical arrangement of conjugated rod building blocks may provide a new strategy for the design of one-dimensional nanostructured materials with biomimetic, electronic, and photonic functions.
• Self-Assembling Molecular Trees Containing Octa-<i>p</i>-phenylene:  From Nanocrystals to Nanocapsules
  作者：Yong-Sik Yoo、Jin-Ho Choi、Ji-Ho Song、Nam-Keun Oh、Wang-Cheol Zin、Soojin Park、Taihyun Chang、Myongsoo Lee

  DOI：10.1021/ja048856h

  日期：2004.5.1

  Tree-shaped molecules consisting of octa-p-phenylene as a stem segment and oligoether dendrons as a flexible head were synthesized and characterized. The molecular tree based on a small flexible head self-assembles into a lamellar structure, whereas the molecule based on a larger headgroup self-assembles into a discrete heptameric bundle that organizes into a 3-D primitive orthorhombic supercrystals, as confirmed by X-ray scatterings and transmission electron microscopic (TEM) observations. Optical studies revealed that the absorption and emission maxima and absorption edge of the 3-D structure shift to higher energy compared to those of the lamellar structure. The molecules in dilute solution (THF/ water = 1:10 v/v) were observed to self-assemble into capsule-like hollow aggregates, as confirmed by dynamic and static light scatterings, scanning electron microscopy (SEM), and TEM investigations. These results demonstrate that tree-shaped molecules are capable of packing into organized discrete nanocrystals with parallel arrangement as well as hollow nanocapsules with radial arrangement, depending on the presence of selective solvents for flexible headgroup.