(2-methyl-3-buten-2-yl)dimethylphenylsilane | 94286-53-0

• 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: (2-methyl-3-buten-2-yl)dimethylphenylsilane
• 英文别名: Dimethyl-(2-methylbut-3-en-2-yl)-phenylsilane
• CAS: 94286-53-0
• 化学式: C₁₃H₂₀Si
• 分子量: 204.387
• InChiKey: GXJCHQRSRYRLLV-UHFFFAOYSA-N

物化性质

• 沸点：
  249.3±19.0 °C(Predicted)
• 密度：
  0.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (2-methyl-3-buten-2-yl)dimethylphenylsilane 以32%的产率得到
  参考文献：
  名称：

  KIRA, MITSUO;TAKI, TAKAYUKI;SAKURAI, HIDEKI, J. ORG. CHEM., 54,(1989) N4, C. 5647-5648

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3-二甲基丙烯酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 、 2-硝基苯基丝氰酸酯 、 三丁基膦 、 双氧水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 29.0h， 生成 (2-methyl-3-buten-2-yl)dimethylphenylsilane
  参考文献：
  名称：

  Fleming, Ian; Waterson, David, Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1809 - 1813

  摘要：

  DOI：

文献信息

• Regioselective Carboxylation of Silicon-Stabilized Allylic Carbanions and the Synthetic Utility of 2-Silyl-3-butenoates
  作者：Hidemitsu Uno

  DOI：10.1246/bcsj.59.2471

  日期：1986.8

  Carbanions of allylic dimethylphenylsilanes show remarkable regioselectivity toward both carboxylation with carbon dioxide and methylation with methyl iodide. Methylation of these compounds occurred preferentialy at α position, although allyltrimethylsilane and allyltriphenylsilane are known to give γ selectivity toward the same electrophiles. Moreover, their aluminum “ate” complexes react with carbon

  烯丙基二甲基苯基硅烷的碳负离子对二氧化碳的羧化和甲基碘的甲基化都显示出显着的区域选择性。这些化合物的甲基化优先发生在 α 位，尽管已知烯丙基三甲基硅烷和烯丙基三苯基硅烷对相同的亲电试剂具有 γ 选择性。此外，它们的铝“ate”复合物在 a 位置与二氧化碳发生区域选择性反应，而与烯丙基部分的甲基取代模式无关。α-羧化烯丙基硅烷被证明是酯化后 3-（甲氧基羰基）烯丙基阴离子的有用合成子。
• Regio- and Stereochemistry on the Electrophilic Trapping of Allylic Samariums Generated by Reductive Cleavage of Allylic Ethers with (C₅Me₅)₂Sm(thf)_<i>n</i>
  作者：Ken Takaki、Takeshi Kusudo、Shinya Uebori、Tetsushi Nishiyama、Tohru Kamata、Masaki Yokoyama、Katsuomi Takehira、Yoshikazu Makioka、Yuzo Fujiwara

  DOI：10.1021/jo9723016

  日期：1998.6.1

  The C-O bond of allylic benzyl ethers was selectively cleaved with Cp-2*Sm(thf)(n) to give allylic samarium complexes in good yields. Facility of their bond fission has been found to be comparable to that of the corresponding propargylic ethers intermolecularly, but lower intramolecularly. Regio- and stereochemistry on the electrophilic trapping of the allylic complexes thus generated remarkably depended on the nature of the electrophiles. They reacted with carbonyl compounds exclusively from the most substituted terminus of the allylic moieties to yield blanched homoallylic alcohols with anti diasteroselectivity. On the other hand, trapping with silyl chlorides produced linear allylic silanes. Here, a plausible mechanism to account for the difference is proposed.
• Fleming, Ian; Higgins, Dick; Lawrence, Nicholas J., Journal of the Chemical Society. Perkin transactions I, 1992, # 24, p. 3331 - 3350
  作者：Fleming, Ian、Higgins, Dick、Lawrence, Nicholas J.、Thomas, Andrew P.

  DOI：——

  日期：——
• Chemistry of organosilicon compounds. 261. Photochemical 1,3-silyl migration in allylsilanes occurring with inversion of silyl configuration
  作者：Mitsuo Kira、Takayuki Taki、Hideki Sakurai

  DOI：10.1021/jo00285a002

  日期：1989.11
• Fleming Ian, Higgins Dick, Lawrence Nicholas J., Thomas Andrew P., J. Chem. Soc. Perkin Trans. 1, (1992) N 24, S 3331-3349
  作者：Fleming Ian, Higgins Dick, Lawrence Nicholas J., Thomas Andrew P.

  DOI：——

  日期：——