5-(三甲基硅烷基)-2-噻吩甲腈 | 77998-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-(三甲基硅烷基)-2-噻吩甲腈
• 中文别名: 2-氰基-5-三甲基硅噻吩
• 英文名称: 2-cyano-5-trimethylsilylthiophene
• 英文别名: 5-(Trimethylsilyl)thiophene-2-carbonitrile；5-trimethylsilylthiophene-2-carbonitrile
• CAS: 77998-64-2
• 化学式: C₈H₁₁NSSi
• mdl: MFCD09039087
• 分子量: 181.334
• InChiKey: HGJALRLIEMOECV-UHFFFAOYSA-N

物化性质

• 沸点：
  222.5±25.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(三甲基硅烷基)-2-噻吩甲腈 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-氰基噻吩
  参考文献：
  名称：

  取代的2-噻吩基三甲基硅烷的碱解速率。从头开始计算单取代噻吩的酸度

  摘要：

  Rates of cleavage in NaOMe-MeOH at 50°C have been determined for the mono-substituted 2-trimethylsilylthiophens X·C4H2S·SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2-C4HS-SiMe3-2. For several compounds the rate and product isotope effects have also been determined. The energies involved in the process X·C4H3S → X·C4H2S−

  DOI：

  10.1016/s0022-328x(00)84581-7
• 作为产物：
  描述：

  2-氰基噻吩 、 (三氟甲基)三甲基硅烷 在 rubidium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到5-(三甲基硅烷基)-2-噻吩甲腈
  参考文献：
  名称：

  三氟甲基三烷基硅烷与氟化物对官能化芳烃和杂芳烃的去质子化CHH甲硅烷基化

  摘要：

  使用被碱金属氟化物活化的Ruppert-Prakash试剂（TMSCF 3），开发了功能化芳烃和杂芳烃的高选择性C-H甲硅烷基化反应。TMSCF 3被认为是温和碱的前体以及亲电子体具有双重作用。甲硅烷基化与敏感的官能团如卤素和硝基相容。

  DOI：

  10.1021/ol503671b

文献信息

• Deprotonative C–H Silylation of Functionalized Arenes and Heteroarenes Using Trifluoromethyltrialkylsilane with Fluoride
  作者：Midori Sasaki、Yoshinori Kondo

  DOI：10.1021/ol503671b

  日期：2015.2.20

  A highly selective C–H silylation reaction of functionalized arenes and heteroarenes was developed using Ruppert–Prakash reagent (TMSCF3) activated by alkali metal fluoride. TMSCF3 is considered to play dual roles as a precursor of a mild base and also as a silicon electrophile. The silylation is compatible with sensitive functional groups such as halogen and nitro groups.

  使用被碱金属氟化物活化的Ruppert-Prakash试剂（TMSCF 3），开发了功能化芳烃和杂芳烃的高选择性C-H甲硅烷基化反应。TMSCF 3被认为是温和碱的前体以及亲电子体具有双重作用。甲硅烷基化与敏感的官能团如卤素和硝基相容。
• Deprotonative Silylation of Aromatic C–H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride
  作者：Kanako Nozawa-Kumada、Sayuri Osawa、Midori Sasaki、Isabelle Chataigner、Masanori Shigeno、Yoshinori Kondo

  DOI：10.1021/acs.joc.7b01525

  日期：2017.9.15

  method for the deprotonative silylation of aromatic C–H bonds has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert–Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF3SiMe3 is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied

  已经开发了一种使用三氟甲基三甲基硅烷（CF 3 SiMe 3，Ruppert-Prakash试剂）和催化量氟化物的芳香族C-H键去质子化甲硅烷基化的方法。在该反应中，认为CF 3 SiMe 3用作碱和亲电子硅。该过程高度耐受杂芳烃和苯上的各种官能团。此外，该方法可以应用于TAC-101的含三甲基甲硅烷基的类似物的合成，TAC-101是对视黄酸受体α（RAR-α）结合具有选择性亲和力的生物活性合成类视黄醇。我们还报告了甲硅烷基化产物进一步转变为有用的衍生物的过程。
• The rates of base cleavage of substituted 2-thienyltrimethylsilanes. AB initio calculations of the acidities of monosubstituted thiophens
  作者：Giancarlo Seconi、Colin Eaborn、John G. Stamper

  DOI：10.1016/s0022-328x(00)84581-7

  日期：1981.1

  NaOMe-MeOH at 50°C have been determined for the mono-substituted 2-trimethylsilylthiophens X·C4H2S·SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2-C4HS-SiMe3-2. For several compounds the rate and product isotope effects have also been determined. The energies involved in the process X·C4H3S → X·C4H2S− for deprotonation at

  Rates of cleavage in NaOMe-MeOH at 50°C have been determined for the mono-substituted 2-trimethylsilylthiophens X·C4H2S·SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2-C4HS-SiMe3-2. For several compounds the rate and product isotope effects have also been determined. The energies involved in the process X·C4H3S → X·C4H2S−