(1,1-二甲基乙基)二甲基[(1-甲基-3-丁炔基)氧基]硅烷 | 80186-44-3

• 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
• 中文名称: (1,1-二甲基乙基)二甲基[(1-甲基-3-丁炔基)氧基]硅烷
• 英文名称: 4-<(dimethyl-tert-butylsilyl)oxy>-1-pentyne
• 英文别名: tert-butyldimethyl(pent-4-yn-2-yloxy)silane；(+/-)-4-tert-butyldimethylsiloxypent-1-yne；rac-4-(tert-Butyldimethylsiloxy)-1-pentyne；4-(dimethyl-tert-butylsilyloxy)-1-pentyne；4-(tert-butyldimethylsilyloxy)-1-pentyne；4-(tert-butyldimethylsilyloxy)pent-1-yne；Silane, (1,1-dimethylethyl)dimethyl[(1-methyl-3-butynyl)oxy]-；tert-butyl-dimethyl-pent-4-yn-2-yloxysilane
• CAS: 80186-44-3
• 化学式: C₁₁H₂₂OSi
• 分子量: 198.381
• InChiKey: YVRDZCNSSRJGLF-UHFFFAOYSA-N

物化性质

• 沸点：
  206.2±13.0 °C(Predicted)
• 密度：
  0.839±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙醚、己烷

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1,1-二甲基乙基)二甲基[(1-甲基-3-丁炔基)氧基]硅烷 在 重铬酸吡啶 、 lithium amide 、 氢氟酸 、 氨 、 sodium 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 (4E)-4-庚烯-2-酮
  参考文献：
  名称：

  Identification of a novel moth sex pheromone inEriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its phylogenetic implications

  摘要：

  Extracts from different body parts of adult female Eriocrania cicatricella (Zett.) were tested for electrophysiological activity on conspecific male antennae. Extracts from the Vth abdominal segment, containing a pair of exocrine glands, elicited the largest electroantennographic response when compared to extracts of other body parts. Female extracts were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). The EAD active peaks were identified as (Z)-4-hepten-2-one, (2R)-heptane-2-ol, and (2R)-(Z)-4-hepten-2-ol by coinjection on a gas chromatography and by comparison of mass spectra with those of synthetic standards. In field tests, a blend of these three pheromone components was highly attractive to conspecific males, and a subtractive assay confirmed that the unsaturated alcohol is the major pheromone component, whereas no definite behavioral activity could be assigned to the ketone or the saturated alcohol. A bait containing the two alcohols with S-configuration was attractive to male E. sparrmannella (Bosc), whereas no males of E. cicatricella were found in these traps. The sex pheromone compounds in E. cicatricella are chemically similar to pheromones reported in Trichoptera and they are produced in homologous glands.

  DOI：

  10.1007/bf02033660
• 作为产物：
  描述：

  4-戊炔-2-醇 生成 (1,1-二甲基乙基)二甲基[(1-甲基-3-丁炔基)氧基]硅烷
  参考文献：
  名称：

  （S）-（-）-austrocorticin和（S）-（+）-dermolactone的合成：天然产物的绝对立体化学。

  摘要：

  分别使用手性二烯6a md 6b合成蒽醌（S）-（-）-austrocorticin（9）和（S）-（+）-过内酯（2）；与这些合成化合物的比较表明，天然奥古柯汀具有（R）绝对构型，而dermolactone是作为（S）异构体占主导地位的对映异构体混合物天然存在的

  DOI：

  10.1016/s0040-4039(00)93405-1

文献信息

• Synthesis and absolute configuration of a constitutionally-new [5.6] spiroacetal from B. tryoni (Queensland fruit fly)
  作者：Yvonne K. Booth、Patricia Y. Hayes、Christopher J. Moore、Lynette K. Lambert、William Kitching、James J. De Voss

  DOI：10.1039/b701833a

  日期：——

  A novel spiroacetal, (2S,6R,8S)-2-methyl-8-ethyl-1,7-dioxaspiro[5.6]dodecane (1), has been identified from the volatile secretions of female B. tryoni by mass spectral analysis and synthesis of an authentic, enantioenriched sample.

  从雌性B. tryoni的挥发性分泌物通过质谱分析和合成真实的，富含对映体的样品。
• Synthesis of <i>E</i>-Alkyl Alkenes from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides with B-Alkenyl-9-borabicyclo[3.3.1]nonanes
  作者：Thomas Di Franco、Alexandre Epenoy、Xile Hu

  DOI：10.1021/acs.orglett.5b02482

  日期：2015.10.2

  The first Ni-catalyzed Suzuki–Miyaura coupling of alkyl halides with alkenyl-(9-BBN) reagents is reported. Both primary and secondary alkyl halides including alkyl chlorides can be coupled. The coupling method can be combined with hydroboration of terminal alkynes, allowing the expedited synthesis of functionalized alkyl alkenes from readily available alkynes with complete (E)-selectivity in one pot

  据报道，烷基卤化物与烯基-（9-BBN）试剂的首次Ni催化的Suzuki-Miyaura偶联反应。包括烷基氯化物的伯烷基卤和仲烷基卤都可以偶联。该偶联方法可以与末端炔烃的硼氢化反应结合使用，从而允许在一个反应​​釜中从容易获得的炔烃以完全的（E）选择性加速合成官能化的烷基烯烃。该方法用于天然大环内酯（±）-瑞奇奥利特的全合成。
• A mild and efficient palladium-catalyzed homocoupling of lithium alkynyltriisopropoxyborates: a new route to synthesis of 1,3-diynes
  作者：Chang Ho Oh、V.Raghava Reddy

  DOI：10.1016/j.tetlet.2004.05.033

  日期：2004.6

  Lithium alkynyltriisopropoxyborates were homocoupled in the presence of palladium acetate and DPEPhos. This protocol allows a new efficient route to synthesis of 1,3-diynes under very mild conditions.

  炔基三异丙氧基硼酸锂在乙酸钯和DPEPhos的存在下均偶联。该方案允许在非常温和的条件下合成1,3-二炔的新有效途径。
• Palladium/copper-catalyzed tandem Sonogashira coupling/lactonization of methyl 2-(2′,2′-dibromovinyl)benzoate with terminal alkynes: Facile access to 3-alkynyl isocoumarins
  作者：Xiaozu Liu、Guojun Chen、Yuxiang Zhou、Peijun Liu

  DOI：10.1016/j.tetlet.2018.07.017

  日期：2018.8

  An efficient palladium/copper-catalyzed tandem Sonogashira reaction/lactonization of methyl 2-(2′,2′-dibromovinyl)benzoate with terminal alkynes has been developed. This facile and direct approach furnishes a variety of 3-alkynyl isocoumarins in moderate to good yields under mild reaction conditions. Furthermore, this method enables concise total synthesis of natural products 3′-hydroxycorfin and gymnopalynes

  已经开发了一种有效的钯/铜催化串联Sonogashira反应/ 2-（2'，2'-二溴乙烯基）苯甲酸甲酯与末端炔烃的内酯化。这种简便而直接的方法可在温和的反应条件下以中等至良好的产率提供各种3-炔基异香豆素。此外，该方法能够简明地完全合成天然产物3'-羟基皮质醇和裸gym草烯酮A。
• Fromα,β-Unsaturated Fischer Carbene Complexes to Highly Substituted 3-Ethoxycyclopentadienes, Masked Cyclopentenones
  作者：Yao-Ting Wu、Bernard Flynn、Heiko Schirmer、Frank Funke、Stefan Müller、Thomas Labahn、Markus Nötzel、Armin de Meijere

  DOI：10.1002/ejoc.200300534

  日期：2004.2

  cyclopentenones 21 could be either eliminated or transformed into other functional groups via the quaternary ammonium salts 24. The elimination product, cyclopentadienone 27 can undergo dimerization either by a formal [4+2] or [2+2] cycloaddition. Cyclopentenone 21naaa with a bromovinyl-terminated side chain undergoes an intramolecular Heck reaction to form 5-methyl-4,6-dimethylenebicyclo[3.3.0]oct-1-en-3-one

  β-氨基取代的 α,β-不饱和 Fischer 卡宾配合物 3 很容易通过四步一锅法从末端炔烃、六羰基铬和仲胺中获得（24 个实例的产率为 68-99%，7 个实例的产率26-63%）。配合物 3 与不同炔烃（包括二炔和烯炔）在供体溶剂（如吡啶或乙腈）中进行正式的 [3+2] 环加成，得到高度取代的 5-（二烷基氨基）-3-乙氧基环戊二烯 7，通常产率中等至极好（25 个例子）产率为 60-95% 和 7 个实施例的产率为 18-53%）。卡宾配合物上的取代基和引入的炔烃对成环反应的区域和立体选择性的空间和电子效应已经详细说明。一个有趣的 1,5- 或更可能的 1，对于在 C-5 处具有三甲基甲硅烷基和 iPr 取代基的 5-(二甲氨基)-3-乙氧基环戊二烯，观察到二甲氨基的 2-迁移。尝试从具有手性氨基或取代基的配合物 3 不对称合成环戊二烯 7 仅取得了中等程度的成功。在仲氨基的手性中心，类型