1-(trimethylsilylethynyl)isoquinoline | 86521-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(trimethylsilylethynyl)isoquinoline
• 英文别名: 1-trimethylsilylethynylisoquinoline；1-((Trimethylsilyl)ethynyl)isoquinoline；2-isoquinolin-1-ylethynyl(trimethyl)silane
• CAS: 86521-10-0
• 化学式: C₁₄H₁₅NSi
• 分子量: 225.365
• InChiKey: UCIUBLLCEWITIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(trimethylsilylethynyl)isoquinoline 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以71%的产率得到1-乙炔-异喹啉
  参考文献：
  名称：

  A Facile Synthesis of Ethynyl-Substituted Six-MemberedN-Heteroaromatic Compounds

  摘要：

  DOI：

  10.1055/s-1983-30319
• 作为产物：
  描述：

  1-羟基异喹啉 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(trimethylsilylethynyl)isoquinoline
  参考文献：
  名称：

  Ru(II) coordination compounds of N N bidentate chelators with 1,2,3 triazole and isoquinoline subunits: Synthesis, spectroscopy and antimicrobial properties

  摘要：

  Bidentate chelators 1 -(1-benzyl-1,2,3-triazol-4-yl)isoquinoline and 3-(1-benzyl-1,2,3-triazol-4-yl)isoquinoline were prepared from benzyl bromide and trimethylsilylethynylisoquinoline precursors using a tandem deprotection/substitution/CuAAC synthetic approach. Each chelator is capable of forming a stable 3:1 Ru(II) coordination compound, which forms as a geometric isomer mixture. These Ru(II) complexes possess unique MLCT absorbance signatures at 450/472 nm (1-isomer) and 367 nm (3-isomer) relative to their constituent chelating units. Minimum inhibitory concentration values as low as 0.4 mu M are observed for Ru(II) complexes against representative Gram-positive bacteria Bacillus subtilis and Staphylococcus epidermidis. Comparing the MIC values of these isoquinoline compounds with analogous 2-(1-benzyl-1,2,3-triazol-4-yl)pyridine compounds shows a 2.5- to 40-fold improvement in potency. This study establishes that increased hydrophobicity introduced at the central chelating units of Ru(II) coordination compounds can be a useful means by which to optimize antimicrobial activity that is complimentary to the variation of peripheral substituent identity at the chelator's N1 triazole position. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2019.114259

文献信息

• Enantioselective Synthesis of Axially Chiral 1-Arylisoquinolines by Rhodium-Catalyzed [2+2+2] Cycloaddition
  作者：Norifumi Sakiyama、Daiki Hojo、Keiichi Noguchi、Ken Tanaka

  DOI：10.1002/chem.201003134

  日期：2011.2.1

  the application! An enantioselective synthesis of axially chiral 1‐arylisoquinolines has been achieved, which involves a rhodium‐catalyzed [2+2+2] cycloaddition of diphenylphosphinoyl‐substituted 1‐arylisoquinolines (see scheme). The new diphenylphosphinoyl‐substituted axially chiral 1‐arylisoquinolines were successfully derivatized to the corresponding axially chiral P,N ligand and Lewis base catalyst

  全部都在应用程序中！已经实现了轴向手性1-芳基异喹啉的对映选择性合成，其中涉及二苯基膦酰基取代的1-芳基异喹啉的铑催化的[2 + 2 + 2]环加成反应（参见方案）。新的二苯基膦酰基取代的轴向手性1-芳基异喹啉已成功衍生为相应的轴向手性P，N配体和路易斯碱催化剂。
• Palladium-catalyzed coupling of heteroaromatic triflates with acetylene and its application for a dynemicin a intermediate
  作者：Takaaki Okita、Minoru Isobe

  DOI：10.1016/0040-4020(95)00118-r

  日期：1995.3

  An acetylene moiety was introduced to a carbonyl carbon of amide group via its triflate in the presence of palladium catalyst, The reaction proceeded smoothly under mild conditions. Utilizing this methodology, a model compound of dynemicin A bearing acetylene group was synthesized.
• SAKAMOTO, TAKAO;SHIRAIWA, MASAFUMI;KONDO, YOSHINORI;YAMANAKA, HIROSHI, SYNTHESIS, BRD, 1983, N 4, 312-314
  作者：SAKAMOTO, TAKAO、SHIRAIWA, MASAFUMI、KONDO, YOSHINORI、YAMANAKA, HIROSHI

  DOI：——

  日期：——
• A Facile Synthesis of Ethynyl-Substituted Six-Membered<i>N</i>-Heteroaromatic Compounds
  作者：Takao Sakamoto、Masafumi Shiraiwa、Yoshinori Kondo、Hiroshi Yamanaka

  DOI：10.1055/s-1983-30319

  日期：——
• Ru(II) coordination compounds of N N bidentate chelators with 1,2,3 triazole and isoquinoline subunits: Synthesis, spectroscopy and antimicrobial properties
  作者：Nicholas W. Kreofsky、Maxwell D. Dillenburg、Eric M. Villa、James T. Fletcher

  DOI：10.1016/j.poly.2019.114259

  日期：2020.2

  Bidentate chelators 1 -(1-benzyl-1,2,3-triazol-4-yl)isoquinoline and 3-(1-benzyl-1,2,3-triazol-4-yl)isoquinoline were prepared from benzyl bromide and trimethylsilylethynylisoquinoline precursors using a tandem deprotection/substitution/CuAAC synthetic approach. Each chelator is capable of forming a stable 3:1 Ru(II) coordination compound, which forms as a geometric isomer mixture. These Ru(II) complexes possess unique MLCT absorbance signatures at 450/472 nm (1-isomer) and 367 nm (3-isomer) relative to their constituent chelating units. Minimum inhibitory concentration values as low as 0.4 mu M are observed for Ru(II) complexes against representative Gram-positive bacteria Bacillus subtilis and Staphylococcus epidermidis. Comparing the MIC values of these isoquinoline compounds with analogous 2-(1-benzyl-1,2,3-triazol-4-yl)pyridine compounds shows a 2.5- to 40-fold improvement in potency. This study establishes that increased hydrophobicity introduced at the central chelating units of Ru(II) coordination compounds can be a useful means by which to optimize antimicrobial activity that is complimentary to the variation of peripheral substituent identity at the chelator's N1 triazole position. (C) 2019 Elsevier Ltd. All rights reserved.