3-Methoxyprop-1-ynyl-diphenyl-prop-2-enylsilane | 909805-46-5

• 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: 3-Methoxyprop-1-ynyl-diphenyl-prop-2-enylsilane
• CAS: 909805-46-5
• 化学式: C₁₉H₂₀OSi
• 分子量: 292.453
• InChiKey: UCKXDOUZRFDZFR-UHFFFAOYSA-N

物化性质

• 沸点：
  354.1±42.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  3-Methoxyprop-1-ynyl-diphenyl-prop-2-enylsilane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 silver hexafluoroantimonate 、 三苯基膦氯金 作用下， 以 二氯甲烷 为溶剂， 20.0~40.0 ℃ 、3.0 Pa 条件下， 生成 (3E,6Z)-4-Methoxymethyl-8-methyl-7-(1-methylene-pentyl)-2,2-diphenyl-5,8-dihydro-2H-[1,2]oxasilocine
  参考文献：
  名称：

  Gold-Catalyzed Intramolecular Allylation of Silyl Alkynes Induced by Silane Alcoholysis

  摘要：

  The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.

  DOI：

  10.1021/ja062560p
• 作为产物：
  描述：

  二苯基二甲氧基硅烷 以 四氢呋喃 、 乙醚 为溶剂， 生成 3-Methoxyprop-1-ynyl-diphenyl-prop-2-enylsilane
  参考文献：
  名称：

  环甲硅烷基环的环应变促进烯丙基转移

  摘要：

  rh氧化物催化时，中型环的环应力的释放促进了C–O键的区域选择性烯丙基转位。通过烯丙基转座，八元环甲硅烷基醚经历环收缩成相应的六元硅氧烷环。

  DOI：

  10.1021/ol2013473

文献信息

• Gold-Catalyzed Intramolecular Allylation of Silyl Alkynes Induced by Silane Alcoholysis
  作者：Sangho Park、Daesung Lee

  DOI：10.1021/ja062560p

  日期：2006.8.1

  The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.
• Ring Strain-Promoted Allylic Transposition of Cyclic Silyl Ethers
  作者：Ivan Volchkov、Sangho Park、Daesung Lee

  DOI：10.1021/ol2013473

  日期：2011.7.1

  Relief of the ring strain of medium-sized rings promotes a regioselective allylic transposition of a C–O bond when catalyzed by rhenium oxide. Through the allylic transposition, eight-membered cyclic silyl ethers undergo ring contraction to the corresponding six-membered siloxacycles.

  rh氧化物催化时，中型环的环应力的释放促进了C–O键的区域选择性烯丙基转位。通过烯丙基转座，八元环甲硅烷基醚经历环收缩成相应的六元硅氧烷环。