tert-butyl benzyl((triisopropylsilyl)ethynyl)carbamate | 1085526-69-7

• 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: tert-butyl benzyl((triisopropylsilyl)ethynyl)carbamate
• 英文别名: terf-butyl benzyl((triisopropylsilyl)ethynyl)carbamate；tert-butyl N-benzyl-N-[2-tri(propan-2-yl)silylethynyl]carbamate
• CAS: 1085526-69-7
• 化学式: C₂₃H₃₇NO₂Si
• 分子量: 387.638
• InChiKey: WXIVWWMAQLWTMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl benzyl((triisopropylsilyl)ethynyl)carbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 tert-butyl benzyl(ethynyl)carbamate
  参考文献：
  名称：

  喹啉N-氧化物与ynamides的无金属C8-H官能化

  摘要：

  喹啉N-氧化物与ynamides的无金属C8-H官能化首次通过由Brønsted酸催化将喹啉N-氧化物加成到ynamides产生的喹啉基烯醇中间体的分子内Friedel-Crafts型反应首次公开。各种喹啉N-氧化物和末端 ynamides 被证明是该方法的合适底物。然后开发了一种用于喹啉的无金属直接 C8-H 功能化的一锅法。

  DOI：

  10.1039/d1cc02138a
• 作为产物：
  描述：

  苄胺 在 potassium phosphate 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 tert-butyl benzyl((triisopropylsilyl)ethynyl)carbamate
  参考文献：
  名称：

  钯介导的降冰片烯衍生物与亚酰胺的[2 + 1]环加成反应

  摘要：

  报道了在酰胺和降冰片烯或降冰片二烯之间有效的钯催化的[2 + 1]环加成反应。发现磷铝环烷和钯/仲氧化膦催化体系均能胜任转化，从而可制备氨基亚甲基环丙烷。该反应显示出对各种官能化的双环[2.2.1]庚-2-烯和乙酰胺的普遍适用性。测试了手性磷酸四环四环磷酰胺以对映选择性的方式进行该转化。

  DOI：

  10.1002/adsc.201200903

文献信息

• Regioselective iodoamination of terminal ynamides for the synthesis of α-amino-β,β-diiodo-enamides
  作者：Hai Huang、Luning Tang、Xiaobo Han、Guangke He、Yang Xi、Hongjun Zhu

  DOI：10.1039/c6cc00370b

  日期：——

  A mild and efficient methodology concerning I2/TBHP-mediated intermolecular iodoamination of ynamides with amines for the synthesis of [small alpha]-amino-[small beta],[small beta]-diiodo-enamides was developed. This reaction provides the first intermolecular iodoamination of terminal alkynes...

  开发了一种温和而有效的方法，涉及I2 / TBHP介导的酰胺与胺的分子间碘代胺化反应，用于合成小α-氨基-小β，小β-二碘代酰胺。该反应提供了末端炔烃的首次分子间碘化。
• Pd/Cu-Catalyzed tandem head-to-tail dimerization/cycloisomerization of terminal ynamides for the synthesis of 5-vinyloxazolones
  作者：Luning Tang、Hai Huang、Yang Xi、Guangke He、Hongjun Zhu

  DOI：10.1039/c7ob00381a

  日期：——

  An attractive and novel methodology involving Pd/Cu-catalyzed tandem head-to-tail dimerization/cycloisomerization of terminal ynamides for the synthesis of 3,5-disubstituted oxazolones was developed. Under Pd(PPh3)2Cl2/CuI cooperative catalyzed reaction conditions, it provided efficient access to 5-vinyloxazolones with exceptional functional group tolerance and good chemoselectivity. The control experiments

  开发了一种吸引人的新颖方法，该方法涉及Pd / Cu催化的串联末端甲酰胺的头对尾二聚/环异构化，以合成3,5-二取代的恶唑酮。在Pd（PPh 3）2 Cl 2 / CuI协同催化的反应条件下，它可以有效地获得5-乙烯基恶唑酮，具有出色的官能团耐受性和良好的化学选择性。对照实验表明Pd（PPh 3）2 Cl 2在末端酰胺的二聚作用中起关键作用，并且在分子内环化中显示低催化活性。此外，还描述了产物5-乙烯基恶唑酮的杂狄尔斯-阿尔德反应，可提供高收率的多环恶唑酮。
• Application of Ynamides in the Synthesis of 2-Amidoindoles
  作者：Karin Dooleweerdt、Thomas Ruhland、Troels Skrydstrup

  DOI：10.1021/ol802477d

  日期：2009.1.1

  A Pd-catalyzed, one-pot, two-step synthesis of 2-amidoindoles from ynamides and o-lodoanilines Is reported. A key highlight of this sequence is that after the Sonogashira reaction, intramolecular cyclization to the indole occurs spontaneously without activation of the alkyne.
• Ruthenium-Catalyzed Synthesis of 5-Amino-1,2,3-triazole-4-carboxylates for Triazole-Based Scaffolds: Beyond the Dimroth Rearrangement
  作者：Serena Ferrini、Jay Zumbar Chandanshive、Stefano Lena、Mauro Comes Franchini、Giuseppe Giannini、Andrea Tafi、Maurizio Taddei

  DOI：10.1021/jo502577e

  日期：2015.3.6

  The 5-amino-1,2,3-triazole-4-carboxylic acid is a suitable molecule for the preparation of collections of peptidomimetics or biologically active compounds based on the triazole scaffold. However, its chemistry may be influenced by the possibility of undergoing the Dimroth rearrangement. To overcome this problem, a protocol based on the ruthenium-catalyzed cycloaddition of N-Boc ynamides with azides has been developed to give a protected version of this triazole amino acid. When aryl or alkyl azides are reacted with N-Boc-aminopropiolates or arylynamides, the cycloaddition occurs with complete regiocontrol, while N-Boc-alkyl ynamides yield a mixture of regioisomers. The prepared amino acids were employed for the preparation of triazole-containing dipeptides having the structural motives typical of turn inducers. In addition, triazoles active as HSP90 inhibitors (as compound 41, IC50 = 29 nM) were synthesized.
• Irregularities in the Effect of Potassium Phosphate in Ynamide Synthesis
  作者：Karin Dooleweerdt、Henrik Birkedal、Thomas Ruhland、Troels Skrydstrup

  DOI：10.1021/jo801935b

  日期：2008.12.5

  The yields of ynamides using Hsung's second generation protocol depend substantially on the quality of K3PO4. of K3PO4 from different suppliers were investigated by various techniques, revealing that the use Of pure and anhydrous K3PO4 provides higher ynamide yields in comparison to samples contaminated with hydrates (K3PO4 center dot 1.5H(2)O and K3PO4 center dot 7H(2)O). With high quality K3PO4, a number of ynamides were synthesized in yields of 52-91%. In addition. we report that ynamides can undergo regioselective hydroamination with carbamates.