Diethyl-hexylsilan | 17961-53-4

• 分子结构分类: 有机化合物
• 英文名称: Diethyl-hexylsilan
• 英文别名: diethyl(hexyl)silane
• CAS: 17961-53-4
• 化学式: C₁₀H₂₄Si
• 分子量: 172.386
• InChiKey: RIKJTBZCRSNOCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  Diethyl-hexylsilan 、 奥苷菊环 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 3,3-二甲基-1-丁烯 、 3,4,7,8-四甲基-1,10-菲罗啉 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以50.1 mg的产率得到2-(diethylheptylsilyl)azulene
  参考文献：
  名称：

  Iridium-Catalyzed Dehydrogenative Silylation of Azulenes Based on Regioselective C–H Bond Activation

  摘要：

  Use of an iridium catalyst allowed the efficient dehydrogenative functionalization of C-H bonds of azulenes with the production of hydrogen as the sole byproduct. The reaction occurred with excellent chemo- and regioselectivities to provide 2-silylazulenes even without any directing groups. Effective conjugation through the 2-position of the azulene ring was demonstrated by the unique stimuli-responsiveness against an acidbase reaction.

  DOI：

  10.1021/acs.orglett.5b00575
• 作为产物：
  描述：

  1-己烯 、 二氯二乙基硅烷 生成 Diethyl-hexylsilan
  参考文献：
  名称：

  Communications TO THE EDITOR

  摘要：

  DOI：

  10.1021/jo01048a069

文献信息

• Conversion of alkanes to linear alkylsilanes using an iridium–iron-catalysed tandem dehydrogenation–isomerization–hydrosilylation
  作者：Xiangqing Jia、Zheng Huang

  DOI：10.1038/nchem.2417

  日期：2016.2

  The conversion of inexpensive, saturated hydrocarbon feedstocks into value-added speciality chemicals using regiospecific, catalytic functionalization of alkanes is a major goal of organometallic chemistry. Linear alkylsilanes represent one such speciality chemical—they have a wide range of applications, including release coatings, silicone rubbers and moulding products. Direct, selective, functionalization of alkanes at primary C–H bonds is difficult and, to date, methods for catalytically converting alkanes into linear alkylsilanes are unknown. Here, we report a well-defined, dual-catalyst system for one-pot, two-step alkane silylations. The system comprises a pincer-ligated Ir catalyst for alkane dehydrogenation and an Fe catalyst that effects a subsequent tandem olefin isomerization–hydrosilylation. This method exhibits exclusive regioselectivity for the production of terminally functionalized alkylsilanes. This dual-catalyst strategy has also been applied to regioselective alkane borylations to form linear alkylboronate esters. The selective conversion of abundant and inexpensive alkane feedstocks into value-added speciality chemicals is a significant and challenging goal, and methods for catalytically converting alkanes into useful linear alkylsilanes are unknown, to date. Now, a strategy combining alkane dehydrogenation with regioselective olefin isomerization–hydrosilylation to produce linear alkylsilanes is described.

  将廉价的饱和碳氢化合物原料转化为增值的特种化学品，利用区域选择性的催化官能化烷烃是有机金属化学的主要目标。线性烷基硅烷就是这样的特种化学品——它们有着广泛的应用，包括释放涂层、硅橡胶和成型产品。直接地、选择性地在伯碳氢键上官能化烷烃是很困难的，迄今为止，催化地将烷烃转化为线性烷基硅烷的方法是未知的。在这里，我们报道了一种定义明确的、双催化剂系统，用于一步、两步烷烃硅烷化。该系统由一个用于烷烃脱氢的夹钳配位的铱催化剂和一个用于随后的烯烃异构化-氢硅烷化的铁催化剂组成。这种方法表现出对端功能化烷基硅烷的排他性区域选择性。这种双催化剂策略也已应用于区域选择性的烷烃硼化，形成线性烷基硼酸酯。选择性地将丰富且廉价的烷烃原料转化为增值的特种化学品是一个重大且具有挑战性的目标，迄今为止，催化地将烷烃转化为有用的线性烷基硅烷的方法是未知的。现在，一种结合烷烃脱氢与区域选择性烯烃异构化-氢硅烷化来产生线性烷基硅烷的策略被描述。
• Regioselective Hydrosilylation of Olefins Catalyzed by a Molecular Calcium Hydride Cation
  作者：Danny Schuhknecht、Thomas P. Spaniol、Laurent Maron、Jun Okuda

  DOI：10.1002/anie.201909585

  日期：2020.1.2

  Chemo- and regioselectivity are often difficult to control during olefin hydrosilylation catalyzed by d- and f-block metal complexes. The cationic hydride of calcium [CaH]+ stabilized by an NNNN macrocycle was found to catalyze the regioselective hydrosilylation of aliphatic olefins to give anti-Markovnikov products, while aryl-substituted olefins were hydrosilyated with Markovnikov regioselectivity

  在d和f嵌段金属络合物催化的烯烃氢化硅烷化过程中，化学和区域选择性通常难以控制。发现通过NNNN大环稳定的钙[CaH] +阳离子氢化物催化脂肪族烯烃的区域选择性氢化硅烷化反应，生成抗马尔可夫尼可夫产物，而芳基取代的烯烃则通过马尔可夫尼可夫区域选择性进行氢化硅烷化。乙烯被伯和仲氢硅烷有效地氢化硅烷化，得到二乙基和单乙基化的硅烷。脂肪族氢硅烷优于其他常用的氢硅烷：芳基硅烷（如PhSiH3）经历由亲核氢化物促进的加扰反应，而烷氧基和甲硅烷氧基取代的氢硅烷则产生可分离的烷氧基和甲硅烷氧基钙衍生物。
• Molecular hydrides of divalent ytterbium supported by a macrocyclic ligand: synthesis, structure and olefin hydrofunctionalization catalysis
  作者：Danny Schuhknecht、Khai-Nghi Truong、Thomas P. Spaniol、Laurent Maron、Jun Okuda

  DOI：10.1039/c8cc05152f

  日期：——

  Bis(triphenylsilyl) and dibenzyl ytterbium(II) complexes supported by the macrocyclic polyamine ligand Me4TACD (1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane) reacted with H2 to give the cationic ytterbium hydrides [(Me4TACD)2Yb2(μ2-H)(2+n)](2−n)+ (n = 0, 1). The hydrides catalyzed the H2/D2 isotope exchange as well as hydrogenation and hydrosilylation of 1-hexene.

  大环多胺配体Me 4 TACD（1,4,7,10-四甲基-1,4,7,10-四氮杂十二烷）负载的双（三苯基甲硅烷基）和二苄基（（II）配合物与H 2反应生成阳离子y氢化物[（ME 4 TACD）2的Yb 2（μ 2 -H）（2+ ñ） ] （2- ñ）+（ñ = 0，1）。氢化物催化1-己烯的H 2 / D 2同位素交换以及氢化和氢化硅烷化。