diisopropyl(phenylethynyl)silane | 317374-19-9

• 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: diisopropyl(phenylethynyl)silane
• 英文别名: (Phenylethynyl)di(propan-2-yl)silane；2-phenylethynyl-di(propan-2-yl)silane
• CAS: 317374-19-9
• 化学式: C₁₄H₂₀Si
• 分子量: 216.398
• InChiKey: CBPNDFJBAWTPPC-UHFFFAOYSA-N

物化性质

• 沸点：
  269.3±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  diisopropyl(phenylethynyl)silane 在 potassium fluoride 、 lithium hydroxide 、 potassium tert-butylate 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 生成 2-(1-羟基环己基)-1-苯基乙酮
  参考文献：
  名称：

  Unusual Tandem Alkynylation and trans-Hydrosilylation To Form Oxasilacyclopentenes

  摘要：

  [GRAPHICS]An unusual tandem reaction sequence to form oxasilacyclopentenes from carbonyls and alkynylsilanes in the presence of a catalytic amount of nucleophilic initiator has been discovered. The reaction proceeds readily at room temperature and is applicable to a wide variety of carbonyl substrates. While the reaction scope tolerates variable substitutions on the alkynylsilane, phenylacetylene-derived silane variants consistently achieved the best yield.

  DOI：

  10.1021/ol051996r
• 作为产物：
  描述：

  二异丙基氯代硅烷 、 苯乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 diisopropyl(phenylethynyl)silane
  参考文献：
  名称：

  Unusual Tandem Alkynylation and trans-Hydrosilylation To Form Oxasilacyclopentenes

  摘要：

  [GRAPHICS]An unusual tandem reaction sequence to form oxasilacyclopentenes from carbonyls and alkynylsilanes in the presence of a catalytic amount of nucleophilic initiator has been discovered. The reaction proceeds readily at room temperature and is applicable to a wide variety of carbonyl substrates. While the reaction scope tolerates variable substitutions on the alkynylsilane, phenylacetylene-derived silane variants consistently achieved the best yield.

  DOI：

  10.1021/ol051996r

文献信息

• Highly Efficient Iridium-Catalyzed Oxidation of Organosilanes to Silanols
  作者：Youngjun Lee、Dong Seomoon、Sundae Kim、Hoon Han、Sukbok Chang、Phil Ho Lee

  DOI：10.1021/jo035647r

  日期：2004.3.1

  Hydrolytic oxidation of organosilanes to the corresponding silanols can be performed highly efficiently with a catalyst system of [IrCl(C8H12)]2 under essentially neutral and mild conditions, and various types of silanols are produced in good to excellent yields.

  使用[IrCl（C 8 H 12）] 2催化剂体系，可以在基本上中性和温和的条件下高度有效地将有机硅烷水解氧化为相应的硅烷醇，并且可以以良好至极好的收率生产各种类型的硅烷醇。
• Synthesis of Alkynylmethylidene‐benzoxasiloles through a Rhodium‐Catalyzed Cycloisomerization Involving 1,2‐Silicon and 1,3‐Carbon Migration
  作者：Tomoya Namba、Susumu Kawauchi、Yu Shibata、Hiroshi Kanno、Ken Tanaka

  DOI：10.1002/anie.201612560

  日期：2017.3.6

  2‐(alkynylsilylethynyl)phenols, leading to alkynylmethylidene‐benzoxasiloles through concomitant silicon and carbon migration. This unprecedented cycloisomerization presumably proceeds via the formation of rhodium vinylidenes through 1,2‐silicon migration, followed by 1,3‐carbon (alkyne) migration via the formation of hypervalent silicon centers.

  结果表明，阳离子铑（I）/二苯醚配合物催化2-（炔基甲硅烷基乙炔基）酚的环异构化，通过伴随的硅和碳迁移导致炔基亚甲基-苯并二甲酚。这种空前的环异构化大概是通过1,2-硅迁移形成亚乙烯基铑，然后通过高价硅中心形成1,3-碳（炔）迁移而进行的。
• Rhodium-Catalyzed Synthesis of Silicon-Bridged 1,2-Dialkenylbenzenes via 1,4-Rhodium Migration
  作者：Takuya Miwa、Ryo Shintani

  DOI：10.1021/acs.orglett.9b00167

  日期：2019.3.15

  An efficient synthesis of 1,3-dialkylidene-2,3-dihydro-1H-benzo[c]siloles, a new type of silicon-bridged π-conjugated compounds, was developed from a simple substrate combination of dialkynylsilanes and arylboronic acids under rhodium catalysis through the use of 1,4-rhodium migration. The reaction pathway was probed by deuterium-labeling experiments, and the use of o-tolylboronic acids led to the formation

  由二炔基硅烷与芳基硼酸的简单底物组合研制出一种新型的硅桥联的π-共轭化合物1,3-二亚烷基-2,3-二氢-1H-苯并[ c ]硅的有效合成。铑通过使用1,4-铑迁移催化。通过氘标记实验探查了反应途径，邻甲苯基硼酸的使用通过1,5-铑的迁移导致了六元硅环的形成。
• Nickel/photoredox-catalyzed three-component silylacylation of acrylates via chlorine photoelimination
  作者：Yejin Koo、Sungwoo Hong

  DOI：10.1039/d4sc02164a

  日期：——

  silicon functionalities through a single, redox-neutral process. Key to this reaction is the precise activation of the Si–H bond, achieved through chlorine radical-induced HAT, enabled by the photoelimination of a Ni–Cl bond. Acyl chlorides serve a dual role, functioning as both acylating agents and chloride donors. Our methodology is distinguished by its mild conditions and extensive substrate adaptability

  有机硅化合物在多个学科中的广泛应用引起了人们对其高效合成的浓厚兴趣。尽管烯烃的催化 1,2-甲硅烷基双官能化为组装具有原子和步骤经济性的复杂有机硅框架提供了一种有前途的方法，但其进展受到光氧化还原催化中外部氢原子转移（HAT）试剂的需求的阻碍。在此，我们公开了α，β-不饱和羰基化合物的有效三组分甲硅烷基酰化，利用镍/光氧化还原催化与各种氢硅烷和芳酰氯的协同作用。该方法能够通过单一的氧化还原中性过程将丙烯酸酯直接转化为含有羰基和硅官能团的有价值的结构单元。该反应的关键是 Si-H 键的精确激活，这是通过氯自由基诱导的 HAT 实现的，并通过 Ni-Cl 键的光消除实现。酰氯具有双重作用，既充当酰化剂又充当氯供体。我们的方法以其温和的条件和广泛的底物适应性而著称，显着增强了药物的后期功能化。
• Highly Selective and Practical Hydrolytic Oxidation of Organosilanes to Silanols Catalyzed by a Ruthenium Complex
  作者：Myunghee Lee、Sangwon Ko、Sukbok Chang

  DOI：10.1021/ja003079g

  日期：2000.12.1