(1-naphthyl)chlorodimethylsilne | 17950-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1-naphthyl)chlorodimethylsilne
• 英文别名: chlorodimethyl(naphthalen-1-yl)silane；ClSi(CH3)2-naphth-1-yl；chloro-dimethyl-[1]naphthyl-silane；Chlor-dimethyl-[1]naphthyl-silan；Napthyl dimethyl chlorosilane；chloro-dimethyl-naphthalen-1-ylsilane
• CAS: 17950-84-4
• 化学式: C₁₂H₁₃ClSi
• 分子量: 220.774
• InChiKey: RZVDZQLEAUDZLO-UHFFFAOYSA-N

物化性质

• 沸点：
  280-285 °C
• 密度：
  1.1902 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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-naphthyl)chlorodimethylsilne 在 aluminum oxide 、 四丁基锡 、 rhenium(VII) oxide 作用下， 以 乙醚 、 正庚烷 为溶剂， 反应 7.0h， 生成 1,4-bis(4a-naphthyldimethylsilyl)but-2-ene
  参考文献：
  名称：

  Metathesis reactions of allylsilanes containing bulky aromatic substituents

  摘要：

  Bulky substituents, such as alpha-naphthyl and ferrocenyl groups, do not inhibit the metathesis of allylsilanes on a Re2O7/Al2O3-SnBu4 catalyst system. Metathesis represents a preparative synthetic method for the synthesis of 1,4-bis(alpha-napthyl-dimethylsilyl)- and 1,4-bis(ferrocenyldimethylsilyl)but-2-enes.

  DOI：

  10.1007/bf00961382
• 作为产物：
  描述：

  二甲基甲氧基氯硅烷 、 1-萘基溴化镁, 0.5M IN METHF 生成 (1-naphthyl)chlorodimethylsilne
  参考文献：
  名称：

  LAPKIN I. I.; MUXINA R. G.; KIRILLOV N. F., ZH. OBSHCH. XIMII, 57,(1987) N 1, 146-151

  摘要：

  DOI：

文献信息

• Polymer and metal oxide supported alkali metal naphthalenides: application in the generation of lithium and sodium reagents1Dedicated to Professor Ken Wade on the occasion of his 65th Birthday in recognition of his outstanding contribution to organometallic and inorganic chemistry.1
  作者：Tania R. van den Ancker、Colin L. Raston

  DOI：10.1016/s0022-328x(97)00543-3

  日期：1998.1

  Highly coloured paramagnetic polymer supported lithium 5,5′ and sodium 6,6′ naphthalenide complexes have been prepared from the reaction of THF solutions of lithium and sodium biphenylide with polystyrene bearing –CH2SiMe2(C10H7) groups. Treating chloropropyl functionalised silica, alumina and titania surfaces with H3Al·NMe3 or H3Ga·NMe3 afford hydroxyl depleted surfaces. Successive treatment with

  高度着色的顺磁性聚合物支持的锂5，5'和钠6，6'萘基复合物已经从锂和钠biphenylide用聚苯乙烯轴承-CH的THF溶液的反应制得2森达2（C 10 H ^ 7）的基团。用H 3 Al·NMe 3或H 3 Ga·NMe 3处理氯丙基官能化的二氧化硅，氧化铝和二氧化钛表面提供羟基耗尽的表面。与锂biphenylide连续处理，1-（chlorodimethylsilyl）萘和碱biphenylide得到支持的碱萘基复合物当与范围的有机卤化物，腈和磷酸盐处理，其产生高产率锂和钠试剂，因为发现6，6'和7，7' 。
• Reduction of Allylpalladium(II)chloride Dimer by Formation of Allyloxy­silanes
  作者：Scott Denmark、Russell Smith

  DOI：10.1055/s-2006-951516

  日期：2006.11

  The reduction ofallylpalladium(II)chloride dimer (APC) to a Pd(0) species can be effected by reaction with alkali metal silanolates. The reduction is extremely rapid in the presence of chelating bisphosphine ligands and for a variety of silanolates.

  烯丙基氯化钯 (II) 二聚体 (APC) 还原为 Pd(0) 物质可以通过与碱金属硅烷醇盐反应来实现。在螯合双膦配体和各种硅烷醇化物存在的情况下，还原速度非常快。
• Polymer supported alkali metal naphthalenides: application in the generation of lithium and sodium reagents
  作者：Tania R. van den Ancker、Graeme R. Hanson、Fu-Chin Lee、Colin L. Raston

  DOI：10.1039/a606181h

  日期：——

  Polymer supported lithium and sodium naphthalenide complexes are prepared from the reaction of THF solutions of lithium and sodium biphenylide with polystyrene bearing -CH 2 SiMe 2 (1-C 10 H 7 ) groups, generating highly coloured paramagnetic material, which afford lithium and sodium reagents in high yield when treated with organic halides, nitriles and phosphates.

  聚合物支持的锂和萘二钠络合物是通过锂和萘二钠的THF溶液与带有-CH2SiMe2（1-C10H7）基团的聚苯乙烯反应制备的，生成高色度的顺磁性材料，当与有机卤化物、腈类和磷酸盐反应时，可获得高产量的锂和钠试剂。
• Nickel‐Catalyzed Cross‐Electrophile 1,2‐Silyl‐Arylation of 1,3‐Dienes with Chlorosilanes and Aryl Bromides
  作者：Qiu‐Quan Pan、Liangliang Qi、Xiaobo Pang、Xing‐Zhong Shu

  DOI：10.1002/anie.202215703

  日期：2023.1.23

  silylarylation of 1,3-dienes using chlorosilanes and aryl bromides is reported. The reaction affords 1,2-linear-silylated products, a selectivity that is distinct from those obtained with conventional hydro- and carbosilylation methods. This work shows the possibility to achieve the silyl-functionalization of unsaturated bonds using readily available chlorosilanes.

  报道了使用氯硅烷和芳基溴的镍催化的 1,3-二烯还原性甲硅烷基化反应。该反应提供 1,2-线性甲硅烷基化产物，其选择性不同于使用常规氢化和碳硅烷化方法获得的产物。这项工作表明使用现成的氯硅烷实现不饱和键的甲硅烷基官能化的可能性。
• Oligo‐Condensation Reactions of Silanediols with Conservation of Solid‐State‐Structural Features.
  作者：Jan‐Falk Kannengießer、Bernd Morgenstern、Oliver Janka、Guido Kickelbick

  DOI：10.1002/chem.202303343

  日期：2024.3.15

  Oligo‐ and polysiloxanes are usually prepared by condensation reactions in solvents without control of stereochemistry. Here we present a solventless thermal condensation of stable organosilanols. We investigated the condensation reactions of organosilanediols with different organic substituents, having in common at least one aromatic group. The condensation kinetics of the precursors observed by NMR spectroscopy revealed a strong dependence on temperature, time, and substitution pattern at the silicon atom. SEC measurements showed that chain length increases with increasing condensation temperature and time and lower steric demand of the substituents, which also influences the glass transition temperatures (T_g) of the resulting oligo‐ or polymers. X‐ray diffraction studies of the crystalline silanediols and their condensation products revealed a structural correlation between the substituent location in the crystalline precursors and the formed macromolecules induced by the hydrogen bonding pattern. In certain cases, it is possible to carry out topotactic polymerization in the solid‐state, which has its origin in the crystal structure.

  摘要寡硅氧烷和多硅氧烷通常是在溶剂中通过缩合反应制备的，没有立体化学控制。在这里，我们介绍了一种稳定的有机硅烷醇的无溶剂热缩合反应。我们研究了有机硅二醇与不同有机取代基的缩合反应，这些取代基至少有一个芳香基团。核磁共振光谱观察到的前体缩合动力学显示，硅原子的缩合与温度、时间和取代模式有很大关系。SEC 测量结果表明，随着缩合温度和时间的增加以及取代基立体需求的降低，链长也会增加，这也会影响所得低聚物或聚合物的玻璃化转变温度（Tg）。对结晶硅烷二醇及其缩合产物进行的 X 射线衍射研究表明，结晶前体中的取代基位置与氢键模式诱导形成的大分子之间存在结构相关性。在某些情况下，可以在固态下进行拓扑聚合，而拓扑聚合源于晶体结构。