tert-butyldimethyl-2-(1-hydroxy-2-propyn)phenoxysilane | 853296-76-1

• 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: tert-butyldimethyl-2-(1-hydroxy-2-propyn)phenoxysilane
• 英文别名: 3-(2-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-yn-1-ol；3-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-yn-1-ol
• CAS: 853296-76-1
• 化学式: C₁₅H₂₂O₂Si
• 分子量: 262.424
• InChiKey: HKXRFEACSHISFW-UHFFFAOYSA-N

物化性质

• 沸点：
  324.5±27.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethyl-2-(1-hydroxy-2-propyn)phenoxysilane 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以43%的产率得到3-(2-((tert-butyldimethylsilyl)oxy)phenyl)propiolaldehyde
  参考文献：
  名称：

  Synthesis and evaluation of ( E )-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists

  摘要：

  Novel series of compounds consisting of 2-amidocyclohex-1-ene carboxylate and phenyl parts which are connected by enyne (compounds 2a-f), but-1-yne (compounds 4a-j), and phenylethylene (compounds 5a-f) linkers as HCA2 full agonists were designed and their functional activity using cAMP assay and binding affinity using radioligand (H-3-niacin) binding assay were evaluated. In general, compounds of all three series exhibit similar HCA2 binding and activation profile. However, the activity is strongly dependent on the substituent at the aromatic part of the structure. Among the structures evaluated, the highest affinity and potency in all series were exhibited by compounds containing 4-hydroxy and/or 2-chloro or 2-fluoro substituents. The most active compounds in the enyne and but-1-yne series in the cAMP assay are 2-fluoro, 4-hydroxy and 2-chloro, 4-hydroxy phenyl derivatives 2f, 4f, and 4g showing potency similar to the previously described 4-hydroxy-biphenyl analogue 5c. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.06.028
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.08h， 生成 tert-butyldimethyl-2-(1-hydroxy-2-propyn)phenoxysilane
  参考文献：
  名称：

  Synthesis and evaluation of ( E )-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists

  摘要：

  Novel series of compounds consisting of 2-amidocyclohex-1-ene carboxylate and phenyl parts which are connected by enyne (compounds 2a-f), but-1-yne (compounds 4a-j), and phenylethylene (compounds 5a-f) linkers as HCA2 full agonists were designed and their functional activity using cAMP assay and binding affinity using radioligand (H-3-niacin) binding assay were evaluated. In general, compounds of all three series exhibit similar HCA2 binding and activation profile. However, the activity is strongly dependent on the substituent at the aromatic part of the structure. Among the structures evaluated, the highest affinity and potency in all series were exhibited by compounds containing 4-hydroxy and/or 2-chloro or 2-fluoro substituents. The most active compounds in the enyne and but-1-yne series in the cAMP assay are 2-fluoro, 4-hydroxy and 2-chloro, 4-hydroxy phenyl derivatives 2f, 4f, and 4g showing potency similar to the previously described 4-hydroxy-biphenyl analogue 5c. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.06.028

文献信息

• Palladium-catalyzed cyclization reactions of propargylic carbonates with nucleophiles: a methodology for the syntheses of substituted 2,3-dihydrofurans and benzofurans
  作者：Masahiro Yoshida、Yukio Morishita、Mika Fujita、Masataka Ihara

  DOI：10.1016/j.tet.2005.02.077

  日期：2005.5

  by the palladium-catalyzed reaction of 5-methoxycarbonyloxy-3-pentyn-1-ol with phenols. The propargylic carbonate containing a nucleophilic phenoxy group also reacted in the presence of palladium to produce the product. The reaction of 1-(2-hydroxyphenyl)-3-methoxycarbonyloxy-1-propyne with 2-methyl-1,3-cyclohexanedione or 2-methyl-1,3-cycohexanedione yielded the substituted benzofurans. The propargylic

  通过钯催化5-甲氧基羰基氧基-3-戊炔-1-醇与酚的反应，合成了苯氧基取代的2,3-二氢呋喃。含有亲核苯氧基的碳酸炔丙酯也可在钯存在下反应生成产物。1-（2-羟基苯基）-3-甲氧基羰氧基-1-丙炔与2-甲基-1,3-环己二酮或2-甲基-1,3-环己二酮的反应产生了取代的苯并呋喃。具有乙酰氧基作为离去基团的炔丙基化合物表现出相似的反应性。
• p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocycles
  作者：Maud Jacubert、Olivier Provot、Jean-François Peyrat、Abdallah Hamze、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1016/j.tet.2010.03.055

  日期：2010.5

  Regioselective hydration of a wide range of internal alkynes has been afforded in high to good yields by using PTSA in EtOH. The scope of the reaction of alkynes has been delineated. Arylaliphatic alkynes and diarylalkynes were regioselectively hydrated in good to excellent yields and short reaction times when the reaction was achieved under microwave irradiation. Moreover, diarylalkynes, arylenynes

  通过在EtOH中使用PTSA，可以实现高产率到良好产率的多种内部炔烃的区域选择性水合。已经描述了炔烃的反应范围。当在微波辐射下完成反应时，芳基脂族炔烃和二芳基炔烃以良好至优异的产率和短的反应时间进行区域选择性水合。而且，对在邻位带有甲氧基或硫代甲基取代基的二芳基炔，芳炔和二芳基二炔进行区域选择性5-内酯化。-dig-环化得到各种2-芳基-和2-苯乙烯基苯并呋喃或苯并噻吩衍生物。我们相信，这种新的无金属污染的环保方法与微波辐射相结合，对于绿色实验室规模的合成研究将非常重要。