trimethylsilanyl-methylammonium hydrochloride | 18166-01-3

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: trimethylsilanyl-methylammonium hydrochloride
• 英文别名: (trimethylsilyl)methanammonium chloride；C-trimethylsilanyl-methylamine; hydrochloride；C-Trimethylsilyl-methylamin; Hydrochlorid；1-(trimethylsilyl)-methylamine, hydrochloride；Methylamine, 1-(trimethylsilyl)-, hydrochloride；trimethylsilylmethanamine;hydrochloride
• CAS: 18166-01-3
• 化学式: C₄H₁₄NSi*Cl
• 分子量: 139.7
• InChiKey: UADAEAZARMYWSK-UHFFFAOYSA-N

物化性质

• 熔点：
  240-241 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  D-erythronolactone acetonide 、 trimethylsilanyl-methylammonium hydrochloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以79%的产率得到5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid trimethylsilanylmethyl amide
  参考文献：
  名称：

  Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids

  摘要：

  An intramolecular non-stabilized azomethine ylide dipolar cycloaddition was applied toward the first non-racemic synthesis of the fully oxygenated bridged pyrrolizidine core (45) of (+)-stemofoline (1) in 11 steps from a commercially available starting material. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.008
• 作为产物：
  描述：

  氯甲基三甲基硅烷 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 160.0 ℃ 、2.41 MPa 条件下， 反应 0.17h， 以73%的产率得到trimethylsilanyl-methylammonium hydrochloride
  参考文献：
  名称：

  连续流动中由氢氧化铵和羟胺化学选择性合成胺的方法

  摘要：

  连续流动实现烷基溴和氯化物与氨水和羟胺的化学选择性胺化，以高收率生产伯铵盐和羟胺。设计了在线后处理以分离相应的伯胺，该伯胺也可通过进一步反应进行缩合，例如酰化和Paal-Knorr吡咯合成。单取代的环氧化物也与反应条件相容。

  DOI：

  10.1021/acs.joc.8b02387

文献信息

• Probing Ligand Binding Sites on Large Proteins by Nuclear Magnetic Resonance Spectroscopy of Genetically Encoded Non-Canonical Amino Acids
  作者：Kasuni B. Ekanayake、Mithun C. Mahawaththa、Haocheng Qianzhu、Elwy H. Abdelkader、Josemon George、Sven Ullrich、Rhys B. Murphy、Sarah E. Fry、Jason Johansen-Leete、Richard J. Payne、Christoph Nitsche、Thomas Huber、Gottfried Otting

  DOI：10.1021/acs.jmedchem.3c00222

  日期：——

  N6-(((trimethylsilyl)-methoxy)carbonyl)-l-lysine (TMSK) and N6-trifluoroacetyl-l-lysine (TFAK) are non-canonical amino acids, which can be installed in proteins by genetic encoding. In addition, we describe a new aminoacyl-tRNA synthetase specific for N6-(((trimethylsilyl)methyl)-carbamoyl)-l-lysine (TMSNK), which is chemically more stable than TMSK. Using the dimeric SARS-CoV-2 main protease (Mpro)

  N 6 -(((三甲基甲硅烷基)-甲氧基)羰基) -l-赖氨酸(TMSK)和N 6 -三氟乙酰基-l-赖氨酸(TFAK)是非规范氨基酸，可以通过基因编码安装在蛋白质中。此外，我们描述了一种特异于N 6 -(((三甲基甲硅烷基)甲基)-氨基甲酰基) -l-赖氨酸 (TMSNK) 的新型氨酰基-tRNA 合成酶，其化学性质比 TMSK 更稳定。使用二聚体 SARS-CoV-2 主蛋白酶 (M pro ) 作为具有三种不同配体的模型系统，我们发现溶剂暴露的三甲基甲硅烷基和 CF 3基团的1 H 和19 F 核在核磁中产生强烈信号共振（NMR）谱。当它们位于活性位点附近而​​不是远离活性位点时，它们对活性位点配体的反应显着不同。相反，NMR 探针未能证实先前报道的配体 pelitinib 的结合位点，该配体被发现可通过促进酶活性二聚体的形成来增强 M pro的活性。总之，氨基酸 TMSK、TMSNK
• Recognition Properties of Acyclic Glycoluril Oligomers
  作者：Derick Lucas、Lyle Isaacs

  DOI：10.1021/ol201636q

  日期：2011.8.5

  The fragmentation reaction of bis-nor-seco-CB[10] with 3,5-dimethylphenol (3) delivers methylene bridged glycoluril pentamer 5 in 81% yield. The host-guest recognition properties of the previously known tetramer 4 and those of pentamer 5 and hexamer 6 toward cationic guests in water are used to delineate some Important features of the binding of acyclic CB[n]-type receptors.
• Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids
  作者：Ryan J. Carra、Matthew T. Epperson、David Y. Gin

  DOI：10.1016/j.tet.2008.02.008

  日期：2008.4

  An intramolecular non-stabilized azomethine ylide dipolar cycloaddition was applied toward the first non-racemic synthesis of the fully oxygenated bridged pyrrolizidine core (45) of (+)-stemofoline (1) in 11 steps from a commercially available starting material. (c) 2008 Elsevier Ltd. All rights reserved.
• Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow
  作者：Clément Audubert、Alexanne Bouchard、Gary Mathieu、Hélène Lebel

  DOI：10.1021/acs.joc.8b02387

  日期：2018.11.16

  bromides and chlorides with aqueous ammonia and hydroxylamine was achieved in continuous flow to produce primary ammonium salts and hydroxylamines in high yields. An in-line workup was designed to isolate the corresponding primary amine, which was also telescoped in further reactions, such as acylation and Paal–Knorr pyrrole synthesis. Monosubstituted epoxides are also compatible with the reaction conditions

  连续流动实现烷基溴和氯化物与氨水和羟胺的化学选择性胺化，以高收率生产伯铵盐和羟胺。设计了在线后处理以分离相应的伯胺，该伯胺也可通过进一步反应进行缩合，例如酰化和Paal-Knorr吡咯合成。单取代的环氧化物也与反应条件相容。

表征谱图