(8-bromooct-1-ynyl)trimethylsilane | 145074-82-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (8-bromooct-1-ynyl)trimethylsilane
• 英文别名: (8-bromooct-1-yn-1-yl)trimethylsilane；8-trimethylsilyl-7-octynyl bromine；8-trimethylsilyl-7-octynyl bromide；8-Bromooct-1-ynyl(trimethyl)silane
• CAS: 145074-82-4
• 化学式: C₁₁H₂₁BrSi
• 分子量: 261.277
• InChiKey: BFZZPHZNIZJOFU-UHFFFAOYSA-N

物化性质

• 沸点：
  256.1±23.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (8-bromooct-1-ynyl)trimethylsilane 生成 trimethyl(oct-1-yn-1-yl)silane
  参考文献：
  名称：

  通过炔烃分子内插入钛-碳键形成碳环

  摘要：

  用路易斯酸EtAlCl 2或Me 2 AlCl处理烷基二茂钛氯化物络合物会导致将束缚的炔烃分子内插入TiC键中。区域选择性炔烃插入产生了由四元，五元和六元环形成的环外三取代烯烃产物。在形成环己烷的情况下，发现炔以顺式立体选择性插入。

  DOI：

  10.1016/s0040-4039(00)60986-3
• 作为产物：
  描述：

  3-辛炔-1-醇 在 正丁基锂 、 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙二胺 为溶剂， 反应 3.5h， 生成 (8-bromooct-1-ynyl)trimethylsilane
  参考文献：
  名称：

  A Generalizable Platform for Interrogating Target- and Signal-Specific Consequences of Electrophilic Modifications in Redox-Dependent Cell Signaling

  摘要：

  Despite the known propensity of small-molecule electrophiles to react with numerous cysteine-active proteins, biological actions of individual signal inducers have emerged to be chemotype-specific. To pinpoint and quantify the impacts of modifying one target out of the whole proteome, we develop a target-protein-personalized "electrophile toolbox" with which specific intracellular targets can be selectively modified at a precise time by specific reactive signals. This general methodology, T-REX (targetable reactive electrophiles and oxidants), is established by (1),constructing a platform that can deliver a range of electronic and sterically different bioactive lipid-derived signaling electrophiles to specific proteins in cells; (2) probing the kinetics of targeted delivery concept, which revealed that targeting efficiency in cells is largely driven by initial on-rate of alkylation; and (3) evaluating the consequences of protein-target- and small-molecule-signal-specific modifications on the strength of downstream signaling These data Show that T-REX allows quantitative interrogations into the extent to which the Nrf2 transcription factor-dependent antioxidant response element (ARE) signaling is activated by selective electrophilic modifications on Keapl protein, one of several redox-sensitive regulators of the Nrf2-ARE axis. The results document Keapl as a promiscuous electrophile-responsive sensor able to respond with similar efficiencies to discrete electrophilic signals, promoting comparable strength of Nrf2-ARE induction. T-REX is also able to elicit cell activation in cases in which whole-cell electrophile flooding fails to stimulate ARE induction prior to causing cytotoxicity. The platform presents a previously unavailable opportunity to elucidate the functional consequences of small-inolecule-signal- and protein-target-specific electrophilic modifications in an otherwise unaffected cellular background.

  DOI：

  10.1021/ja5132648

文献信息

• Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by “click” chemistry
  作者：Himadri Kayal、Mohamed M. Ahmida、Scott Dufour、Hi Taing、S. Holger Eichhorn

  DOI：10.1039/c3tc31588f

  日期：——

  hexamethylene spacers as well as acetylene derivatives with trimethylene spacers unexpectedly display columnar mesophases over ranges of temperature from 30 °C to 110 °C. A thermally activated cross-linking of a hexagonal columnar mesophase by cycloaddition at 65 °C is demonstrated for a 1 : 1 mixture of azide and acetylene derivatives. At this temperature the reaction progresses for up to 48 hours but

  自组织材料的固有缺点是它们易受机械力以及暴露于化学物质和辐射的影响而发生结构变化。所需超分子结构中分子的交联是结构上更稳定的材料的普遍适用途径，但由于自交联基团的引入会影响其自组织和交联过程，因此很难应用于自组织材料。连接可能改变前一相的超分子结构。此处报道的是包含八个末端叠氮化物基团或八个末端乙炔基团的八烷硫基取代的四氮杂卟啉的合成，热性质和交联。这些化合物的合成需要制备含有叠氮化物和炔烃的侧链，并使它们与1,2-二氰基亚乙基-1，2-二硫代酸酯反应为相应的马来腈中间体。通过建立的Mg模板化环四聚体，所有马来腈均成功转化为四氮杂卟啉，典型收率为60-70％。无金属和铜的热性能II通过热重量分析，偏振光学显微镜，差示扫描量热法和可变温度粉末X射线衍射测量研究了金属化的四氮杂卟啉。具有三亚甲基和六亚甲基间隔基的叠氮化物取代的四氮杂卟啉以及具有三亚甲基间隔基的乙炔衍生物出乎意料地在30°C至1
• Synthesis, Characterization, and Application of Muscarinergic M₃ Receptor Ligands Linked to Fluorescent Dyes
  作者：Johannes Köckenberger、Oliver Fischer、Andreas Konopa、Sebastian Bergwinkl、Susanne Mühlich、Peter Gmeiner、Roger Jan Kutta、Harald Hübner、Max Keller、Markus R. Heinrich

  DOI：10.1021/acs.jmedchem.2c01376

  日期：2022.12.22

  Through the linkage of two muscarinergic M3 receptor ligands to fluorescent tetramethylrhodamine- and cyanine-5-type dyes, two novel tool compounds, OFH5503 and OFH611, have been developed. Based on the suitable binding properties and kinetics related to the M3 subtype, both ligand-dye conjugates were found to be useful tools to determine binding affinities via flow cytometric measurements. In addition

  通过将两个毒蕈碱能 M 3受体配体与荧光四甲基罗丹明和花青 5 型染料连接，开发了两种新型工具化合物 OFH5503 和 OFH611。基于与 M 3亚型相关的合适的结合特性和动力学，发现两种配体-染料缀合物都是通过流式细胞术测量确定结合亲和力的有用工具。此外，共聚焦显微镜强调了相对较低的非特异性结合和研究细胞中 M 3受体表达的适用性。除了已证明对 M 3亚型研究有用外，结合物 OFH5503 和 OFH611 还可以，因为它们对 M 1具有高亲和力受体，在毒蕈碱能受体研究领域发展成为更加通用的工具。
• HMPA-Free Synthesis of TMS-Substituted Alkynes
  作者：Marie Cordier、Daniel S. Müller、Marc Devillard

  DOI：10.1021/acs.organomet.4c00091

  日期：2024.5.13

  TMS-substituted alkynes are versatile building blocks in organic synthesis. Traditional synthesis involves alkyne deprotonation and the reaction with TMSCl. Recently, TMS-acetylene has become an increasingly inexpensive bulk chemical, offering an attractive alternative to accessing TMS-substituted alkynes, especially when the alkyne is expensive or not commercially available. However, this route has

  TMS 取代的炔烃是有机合成中的通用结构单元。传统的合成涉及炔烃去质子化以及与 TMSCl 的反应。最近，TMS-乙炔已成为一种越来越便宜的大宗化学品，为获取 TMS 取代的炔烃提供了一种有吸引力的替代品，特别是当炔烃价格昂贵或无法市售时。然而，这条路线是用致癌的HMPA作​​为共溶剂建立的。在这项工作中，我们公开了利用 DMPU 作为 HMPA 替代品的优化条件。
• Kumada−Corriu Reactions of Alkyl Halides with Alkynyl Nucleophiles
  作者：Lian-Ming Yang、Li-Fu Huang、Tien-Yau Luh

  DOI：10.1021/ol049686g

  日期：2004.4.1

  Pd-2(dba)(3)-Ph3P-catalyzed Kumada-Corriu coupling reactions of unactivated alkyl bromides or iodides with an alkynyl nucleophile furnish C-sp-C(sp)3 bond formation, Alkynyl nucleophiles can be alkynyllithiums or the corresponding Grignard reagents. The superior performance of Ph3P ligand over the trialkylphosphine ligands indicates that this cross-coupling reaction may be a reductive-elimination-controlled process.
• Pheromone synthesis. Part 244: Synthesis of the racemate and enantiomers of (11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), a new sex pheromone of male Drosophila melanogaster to show its (S)-isomer and racemate as bioactive
  作者：Kenji Mori、Yasumasa Shikichi、Shruti Shankar、Joanne Y. Yew

  DOI：10.1016/j.tet.2010.06.080

  日期：2010.8

  The enantiomers of (11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol were synthesized from the enantiomers of 3,4-epoxy-1-butanol PMB ether. Its racemate was also synthesized. Its (S)-isomer and racemate were shown to possess the same pheromone activity as CH503, a long-lived inhibitor of male courtship in Drosophila melanogaster, although the racemate was less active. (C) 2010 Elsevier Ltd. All rights reserved.