7-chloro-1-(trimethylsilyl)-1-heptyne | 127016-34-6

• 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: 7-chloro-1-(trimethylsilyl)-1-heptyne
• 英文别名: (7-Chloro-1-heptyn-1-yl)trimethylsilane；7-chlorohept-1-ynyl(trimethyl)silane
• CAS: 127016-34-6
• 化学式: C₁₀H₁₉ClSi
• 分子量: 202.799
• InChiKey: WSEROLZFGLSFOV-UHFFFAOYSA-N

物化性质

• 沸点：
  221.9±23.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  7-chloro-1-(trimethylsilyl)-1-heptyne 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 30.0h， 生成 7-iodo-1-(trimethylsilyl)-1-heptyne
  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
• 作为产物：
  描述：

  1-氯-5-碘戊烷 、 lithium trimethylsilylacetylenide 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 7-chloro-1-(trimethylsilyl)-1-heptyne
  参考文献：
  名称：

  In Situ Selection of Lead Compounds by Click Chemistry:  Target-Guided Optimization of Acetylcholinesterase Inhibitors

  摘要：

  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.

  DOI：

  10.1021/ja043031t

文献信息

• 1,5-annelated 4-methylenecyclopentenes by intramolecular type I zinc-ene reactions followed by Pd(0)-catalyzed cyclization
  作者：J. van der Louw、C.M.D. Komen、A. Knol、F.J.J. de Kanter、J.L. van der Baan、F. Bickelhaupt、G.W. Klumpp

  DOI：10.1016/s0040-4039(00)99387-0

  日期：1989.1

  3-(Alk-m-ynyl)-2-(methoxymethyl)-2-propenylzinc bromides 1 (m = 4,5,6) undergo intramolecular carbometallation. The products 2 were converted by Pd(0)-catalyzed cyclization to 1,5-annelated 4-methylenecyclopentenes 3.

  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。
• 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：——
• 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.
• Intramolecular zinc-ene reactions of alkynes; preparation of 1,5-annulated 4-methylenecyclopentenes
  作者：Jaap van der Louw、Juul L. van der Baan、Corine M.D. Komen、Adri Knol、Franciscus J.J. de Kanter、Friedrich Bickelhaupt、Gerhard W. Klumpp

  DOI：10.1016/s0040-4020(01)89858-6

  日期：1992.1

  Intramolecular Type I zinc-ene reaction of 3-(alk-m-ynyl)-2-(methoxymethyl)-2-propenylzinc bromides 2 (m = 4,5,6) gave five-, six- and seven-membered carbometallation product 3, which on Pd(0)-catalyzed cyclization were converted to 1,5-annulated 4-methylenecyclopentenes 4. Preparation of 4-methylenecyclopentenes by intramolecular Type II zinc-ene reactions of 2-(alk-m-ynyloxymethyl)-2-alkenylzinc

  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。