8-chloro-1-(trimethylsilyl)-1-octyne | 126232-81-3

• 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-chloro-1-(trimethylsilyl)-1-octyne
• 英文别名: 1-trimethylsilyl-8-chloro-1-octyne；8-trimethylsilyl-7-octynyl chloride；8-Chlorooct-1-ynyl(trimethyl)silane
• CAS: 126232-81-3
• 化学式: C₁₁H₂₁ClSi
• 分子量: 216.826
• InChiKey: BBOIAKHDHLCMIK-UHFFFAOYSA-N

物化性质

• 沸点：
  241.6±23.0 °C(Predicted)
• 密度：
  0.901±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 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-chloro-1-(trimethylsilyl)-1-octyne 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 30.0h， 生成 8-iodo-1-(trimethylsilyl)-1-octyne
  参考文献：
  名称：

  炔烃的分子内锌-烯反应；1,5-环化的4-亚甲基环戊烯的制备

  摘要：

  3-（烷基-间-炔基）-2-（甲氧基甲基）-2-丙烯基溴化锌2（m = 4,5,6）的分子内I型锌-烯反应生成五元，六元和七元的碳金属化产物3，其在Pd（0）催化的环化反应中转化为1,5-环化的4-亚甲基环戊烯4。通过2-（烷-间-炔氧基甲基）-2-烯基溴化锌6（m = 2,3）的分子内II型锌-烯反应，然后通过Pd（0）催化的碳金属化产物7的重排，制备4-亚甲基环戊烯不可能。加法和重排很慢或没有发生。

  DOI：

  10.1016/s0040-4020(01)89858-6
• 作为产物：
  描述：

  1-氯-6-碘己烷 、 三甲基乙炔基硅 在 正丁基锂 作用下， 生成 8-chloro-1-(trimethylsilyl)-1-octyne
  参考文献：
  名称：

  通过分子内I型锌-烯反应，然后由Pd（0）催化的环化反应生成1,5-退火的4-亚甲基环戊烯

  摘要：

  3-（烷基-间-炔基）-2-（甲氧基甲基）-2-丙烯基溴化锌1（m = 4,5,6）经历分子内碳金属化反应。产物2通过Pd（0）催化的环化反应转化为1,5-退火的4-亚甲基环戊烯3。

  DOI：

  10.1016/s0040-4039(00)99387-0

文献信息

• METHOD FOR PRODUCING REDUCED HALIDE COMPOUND HAVING UNDERGONE REDUCTION OF CARBON-CARBON UNSATURATED BOND
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US20190322607A1

  公开（公告）日：2019-10-24

  A halide compound having one or more carbon-carbon unsaturated bonds is catalytically reduced with substantially no dehalogenation to produce a reduced halide compound in which at least one of the one or more unsaturated bonds is reduced. Specifically provided is a method for producing a reduced halide compound including steps of: reacting a nickel compound, a zinc compound, and a borohydride compound in a solvent to obtain a reduction catalyst; and subjecting a halide compound having one or more carbon-carbon unsaturated bonds to catalytic reduction in the presence of the reduction catalyst to reduce at least one of the one or more carbon-carbon unsaturated bonds to thereby obtain a reduced halide compound.

  一种卤化物化合物，其具有一个或多个碳-碳不饱和键，经催化还原而几乎不发生去卤反应，以产生一个减少的卤化物化合物，其中至少一个或多个不饱和键被还原。具体提供了一种生产减少的卤化物化合物的方法，包括以下步骤：在溶剂中反应镍化合物、锌化合物和硼氢化物化合物以获得还原催化剂；并在还原催化剂存在的情况下，将具有一个或多个碳-碳不饱和键的卤化物化合物进行催化还原，以减少至少一个或多个碳-碳不饱和键，从而获得减少的卤化物化合物。
• In Situ Selection of Lead Compounds by Click Chemistry:  Target-Guided Optimization of Acetylcholinesterase Inhibitors
  作者：Antoni Krasiński、Zoran Radić、Roman Manetsch、Jessica Raushel、Palmer Taylor、K. Barry Sharpless、Hartmuth C. Kolb

  DOI：10.1021/ja043031t

  日期：2005.5.1

  The target-guided, in situ click chemistry approach to lead discovery has been successfully employed for discovering acetylcholinesterase (AChE) inhibitors by incubating a selected enzyme/tacrine azide combination with a variety of acetylene reagents that were not previously known to interact with the enzyme's peripheral binding site. The triazole products, formed by the enzyme, were identified by HPLC-mass spectrometry analysis of the crude reaction mixtures. The target-guided lead discovery search was also successful when performed with reagent mixtures containing up to 10 components. From 23 acetylene reagents, the enzyme selected two phenyltetrahydroisoquinoline (1310) building blocks that combined with the tacrine azide within the active center gorge to form multivalent inhibitors that simultaneously associate with the active and peripheral binding sites. These new inhibitors are up to 3 times as potent as our previous phenylphenanthridinium-derived compounds, and with dissociation constants as low as 33 femtomolar, they are the most potent noncovalent AChE inhibitors known. In addition, the new compounds lack a permanent positive charge and aniline groups and possess fewer fused aromatic rings. Remarkably, despite the high binding affinity, the enzyme displayed a surprisingly low preference for one IQ enantionner over the other.
• 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.
• Mechanistic Investigations of the Rhodium Catalyzed Propargylic CH Activation
  作者：Urs Gellrich、Antje Meißner、Alberto Steffani、Matthias Kähny、Hans-Joachim Drexler、Detlef Heller、Dietmar A. Plattner、Bernhard Breit

  DOI：10.1021/ja411204d

  日期：2014.1.22

  Previously we reported the redox-neutral atom economic rhodium catalyzed coupling of terminal alkynes with carboxylic acids using the DPEphos ligand. We herein present a thorough mechanistic investigation applying various spectroscopic and spectrometric methods (NMR, in situ-IR, ESI-MS) in combination with DFT calculations. Our findings show that in contrast to the originally proposed mechanism, the catalytic cycle involves an intramolecular protonation and not an oxidative insertion of rhodium in the OH bond of the carboxylic acid. A sigma-allyl complex was identified as the resting state of the catalytic transformation and characterized by X-ray crystallographic analysis. By means of ESI-MS investigations we were able to detect a reactive intermediate of the catalytic cycle.
• LOUW, J. VAN DER;KOMEN, C. M. D.;KNOL, A.;KANTER, F. J. J. DE;BAAN, J. L.+, TETRAHEDRON LETT., 30,(1989) N3, C. 4453-4456
  作者：LOUW, J. VAN DER、KOMEN, C. M. D.、KNOL, A.、KANTER, F. J. J. DE、BAAN, J. L.+

  DOI：——

  日期：——