Silanamine,N-[(4-bromophenyl)methylene]-1,1,1-trimethyl- | 122687-88-1

• 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: Silanamine,N-[(4-bromophenyl)methylene]-1,1,1-trimethyl-
• 英文别名: 1-(4-bromophenyl)-N-trimethylsilylmethanimine
• CAS: 122687-88-1
• 化学式: C₁₀H₁₄BrNSi
• 分子量: 256.217
• InChiKey: CFOJVCUBRFYLHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Silanamine,N-[(4-bromophenyl)methylene]-1,1,1-trimethyl- 在 N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以1.37 g的产率得到4-溴苯腈
  参考文献：
  名称：

  含氧铵盐介导的醛类与腈的接触

  摘要：

  一种可扩展，高产，快速的途径，可通过乙氧基铵盐（4-乙酰氨基-2-2,2,6,6-四甲基哌啶-1-氟肟酸四氟硼酸）和六甲基二硅氮烷（HMDS）介导的醛类中的一系列腈的进入已经被开发出来。该反应可能涉及两个不同的化学转化：HMDS和醛之间可逆的甲硅烷基亚胺形成，然后由氧铵盐介导的氧化和甲硅烷基化反应制得腈。废氧化剂可以容易地回收并用于再生氧铵盐氧化剂。

  DOI：

  10.1002/anie.201412256
• 作为产物：
  描述：

  对溴苯甲醛 、 lithium hexamethyldisilazane 以 四氢呋喃 为溶剂， 以21 g的产率得到Silanamine,N-[(4-bromophenyl)methylene]-1,1,1-trimethyl-
  参考文献：
  名称：

  [EN] PIPERIDINYL INDOLE DERIVATIVES, PREPARATION METHODS AND MEDICINAL USES THEREOF
  [FR] DÉRIVÉS DE PIPÉRIDINYL INDOLE, LEURS PROCÉDÉS DE PRÉPARATION ET LEURS UTILISATIONS MÉDICALES

  摘要：

  Compounds of formula (I) as piperidinyl indole derivatives, the preparation method thereof, pharmaceutical compositions comprising the compounds, and the pharmaceutical uses for the treatment a disease or disorder mediated by complement activation.

  公开号：

  WO2023072197A1

文献信息

• Silyl Imine Electrophiles in Enantioselective Catalysis: A Rosetta Stone for Peptide Homologation, Enabling Diverse <i>N</i>-Protected Aryl Glycines from Aldehydes in Three Steps
  作者：Dawn M. Makley、Jeffrey N. Johnston

  DOI：10.1021/ol501297a

  日期：2014.6.6

  es serve in the Bis(AMidine)-catalyzed addition of bromonitromethane with a high degree of enantioselection. This allows for the production of a range of protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung Amide Synthesis (UmAS). Hence, peptide homologation with nonnatural aryl glycine amino acids is achieved in three steps from aromatic aldehydes, which are plentiful and inexpensive

  我们报告N -（三甲基甲硅烷基）亚胺在双（脒）催化的溴硝基甲烷加成中发挥作用，具有高度的对映选择性。这允许生产一系列受保护的 α-溴硝基烷烃供体（包括 Fmoc），用于 Umpolung 酰胺合成 (UmAS)。因此，与非天然芳基甘氨酸氨基酸的肽同源性是通过三个步骤从芳香醛中实现的，芳香醛丰富且价格低廉。通过避免α-氨基酸中间体，可以避免同源步骤中的差向异构化。
• Asymmetric Synthesis of Propargylamides via 3,3‘-Disubstituted Binaphthol-Modified Alkynylboronates
  作者：T. Robert Wu、J. Michael Chong

  DOI：10.1021/ol0523087

  日期：2006.1.1

  Alkynylboronates derived from 3,3'-disubstituted-2,2'-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective synthesis of the antitubulin agent (-)-N-acetylcolchinol.
• Synthesis, Characterization, and Reactivity Studies of Subphthalocyanine Boron Triflate
  作者：Zikuan Wang、Xuefeng Fu

  DOI：10.1021/acs.organomet.6b00754

  日期：2017.1.23

  The highly reactive subphthalocyanine boron triflate complex ((subPc)BOTf) was isolated and characterized by X-ray diffraction and spectroscopic methods. The combination of (subPc)BOTf and bis(trimethylsilyl)-amide (LiHMDS) yielded a "kinetically induced" frustrated Lewis pair system capable of activating a variety of substrates such as ethers, amides, and ketones. These reactions demonstrate the high reactivity of (subPc)BOTf toward organic molecules.
• Palladium‐Catalyzed Cascade Heck Coupling and Allylboration of Iododiboron Compounds via Diboryl Radicals
  作者：Yi Wei、Xiao‐Yu Xie、Jiabin Liu、Xiaoxiao Liu、Bo Zhang、Xin‐Yi Chen、Shi‐Jun Li、Yu Lan、Kai Hong

  DOI：10.1002/anie.202401050

  日期：2024.4.24

  Geminal bis(boronates) are versatile synthetic building blocks in organic chemistry. The fact that they predominantly serve as nucleophiles in the previous reports, however, has restrained their synthetic potential. Herein we disclose the ambiphilic reactivity of α‐halogenated geminal bis(boronates), of which the first catalytic utilization was accomplished by merging a formal Heck cross‐coupling with a highly diastereoselective allylboration of aldehydes or imines, providing a new avenue for rapid assembly of polyfunctionalized boron‐containing compounds. We demonstrated that this cascade reaction is highly efficient and compatible with various functional groups, and a wide range of heterocycles. In contrast to a classical Pd(0/II) scenario, mechanistic experiments and DFT calculations have provided strong evidence for a catalytic cycle involving Pd(I)/diboryl carbon radical intermediates.