triisopropyl(4-phenylbut-1-yn-1-yl)silane | 82192-72-1

• 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: triisopropyl(4-phenylbut-1-yn-1-yl)silane
• 英文别名: 4-Phenylbut-1-ynyl-tri(propan-2-yl)silane
• CAS: 82192-72-1
• 化学式: C₁₉H₃₀Si
• 分子量: 286.533
• InChiKey: JQWYZBGZQCOZDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  triisopropyl(4-phenylbut-1-yn-1-yl)silane 在 N-碘代丁二酰亚胺 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 六氟异丙醇 为溶剂， 生成 (Z)-(4-iodobut-3-en-1-yl)benzene
  参考文献：
  名称：

  Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D

  摘要：

  The C-Si bonds of triisopropylsilyl-substituted alkenes, 1,3-dienes, and related multifunctional substrates, as well as analogous C-TBDPS and C-TBS bonds, are readily and chemoselectively cleaved with NIS (or other sources of I(+), such as N-iodosaccharin, 1,3-diodohydantoin, and Ipy(2)BF(4)). The desired iodoalkenes are obtained stereospecifically without byproducts, provided that the reactions are carried out in CF(3)CHOHCF(3) and, in general, with 30 mol % of Ag(2)CO(3) (or AgOAc/2,6-Iutidine) as an additive. Fragment C10-C18 of cytotoxic amphidinolides B1-B3 and D has been synthesized using this improved procedure.

  DOI：

  10.1021/ol2020187
• 作为产物：
  描述：

  1-(三异丙基硅基)-1-丙炔 在 正丁基锂 、 四亚甲基二胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.0h， 生成 triisopropyl(4-phenylbut-1-yn-1-yl)silane
  参考文献：
  名称：

  Useful synthetic reagents derived from 1-triisopropylsilylpropyne and 1,3-[triisopropylsilyl]propyne, direct, stereoselective synthesis of either or enynes

  摘要：

  DOI：

  10.1016/s0040-4039(00)86930-0

文献信息

• Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes
  作者：Yadong Gao、Chao Yang、Songlin Bai、Xiaolei Liu、Qingcui Wu、Jing Wang、Chao Jiang、Xiangbing Qi

  DOI：10.1016/j.chempr.2019.12.010

  日期：2020.3

  Transition-metal-catalyzed cross-coupling reactions between naturally abundant sp3-hybridized carbon centers facilitate access to diverse molecules with complex three-dimensional structures. Organometallic compounds are among one of the most powerful reagents that are broadly used in carbon–carbon bond formations. Although sp2-hybridized organometallic compounds are widely employed in cross-couplings, sp3-hybridized

  自然丰富的sp 3-杂化碳中心之间的过渡金属催化交叉偶联反应有助于获得具有复杂三维结构的各种分子。有机金属化合物是最强大的试剂之一，广泛用于碳-碳键的形成。尽管sp 2-杂化的有机金属化合物广泛用于交叉偶联，但是sp 3-杂化的有机金属偶联剂的开发较少。在这里，我们报告可见光诱导的单个镍催化的C（sp 3）–C（sp 3），C（sp 3）–C（sp 2）和C（sp 3）–C（sp）使用烷基锆茂的交叉偶联反应，该反应很容易从末端或内部未活化的烯烃通过加氢锆和链步反应就地生成。该方法温和，适用于多种底物，包括伯，仲，叔烷基，芳基，烯基，炔基卤化物和各种烯烃。机理研究表明，镍催化的自由基交叉偶联是一种新颖的途径，代表了锆锆茂的首次可见光诱导的转变。
• Silver-Catalyzed Decarboxylative Alkynylation of Aliphatic Carboxylic Acids in Aqueous Solution
  作者：Xuesong Liu、Zhentao Wang、Xiaomin Cheng、Chaozhong Li

  DOI：10.1021/ja306638s

  日期：2012.9.5

  C(sp(3))-C(sp) bond formations are of immense interest in chemistry and material sciences. We report herein a convenient, radical-mediated and catalytic method for C(sp(3))-C(sp) cross-coupling. Thus, with AgNO(3) as the catalyst and K(2)S(2)O(8) as the oxidant, various aliphatic carboxylic acids underwent decarboxylative alkynylation with commercially available ethynylbenziodoxolones in aqueous solution

  C(sp(3))-C(sp) 键的形成在化学和材料科学中具有极大的兴趣。我们在此报告了一种方便的、自由基介导的催化方法，用于 C(sp(3))-C(sp) 交叉耦合。因此，以 AgNO(3) 作为催化剂，以 K(2)S(2)O(8) 作为氧化剂，在温和的条件下，各种脂肪族羧酸与市售的乙炔基苯并恶酮在水溶液中进行脱羧炔化。这种特定于位点的炔基化不仅通用且高效，而且与官能团兼容。此外，它表现出显着的化学和立体选择性。
• Copper-Catalyzed Monoborylation of Silylalkynes; Regio- and Stereoselective Synthesis of (<i>Z</i>)-β-(Borylvinyl)silanes
  作者：Yeong Mi Chae、Jun Sung Bae、Jong Hun Moon、Jin Yong Lee、Jaesook Yun

  DOI：10.1002/adsc.201300881

  日期：2014.3.10

  The selective copper‐catalyzed borylation of silylalkynes in the presence of a diboron reagent and methanol produced a variety of (Z)‐β‐(borylvinyl)silanes. The appropriate use of a selective ligand for copper allows the chemo‐, regio‐, and stereoselective monoborylation of silylalkynes. The β‐regioselectivity of an N‐heterocyclic carbene (NHC)‐copper catalyst was investigated by DFT calculations.

  在存在二硼试剂和甲醇的情况下，铜催化的甲硅烷基炔烃的选择性硼化反应生成了各种（Z）-β-（硼乙烯基乙烯基）硅烷。铜的选择性配体的适当使用可实现甲硅烷基炔的化学，区域和立体选择性单硼化。通过DFT计算研究了N-杂环卡宾（NHC）-铜催化剂的β-区域选择性。
• Iron-Catalyzed Cross-Coupling between 1-Bromoalkynes and Grignard-Derived Organocuprate Reagents
  作者：Daniele Castagnolo、Maurizio Botta

  DOI：10.1002/ejoc.201000924

  日期：2010.8

  No abstract is available for this article.

  本文没有摘要。
• Metal-Free CH–CH-Type Cross-Coupling of Arenes and Alkynes Directed by a Multifunctional Sulfoxide Group
  作者：José A. Fernández-Salas、Andrew J. Eberhart、David J. Procter

  DOI：10.1021/jacs.5b12579

  日期：2016.1.27

  A metal-free CH-CH-type coupling of arenes and alkynes, mediated by a multifunctional sulfoxide directing group, exploits nonprefunctionalized coupling partners, proceeds under mild conditions, is operationally simple, and exhibits high functional group tolerance. The products of the CH-CH coupling are highly versatile, and the metal-free process can be used for the construction and late-stage modification of important molecular scaffolds.