(E)-2-Methyl-1-(trimethylsilyl)oct-1-ene | 67399-47-7

• 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: (E)-2-Methyl-1-(trimethylsilyl)oct-1-ene
• 英文别名: trimethyl[(E)-2-methyl-1-octenyl]silane；trimethyl(2-methyloct-1-en-1-yl)silane；trimethyl-[(E)-2-methyloct-1-enyl]silane
• CAS: 67399-47-7
• 化学式: C₁₂H₂₆Si
• 分子量: 198.424
• InChiKey: QOJJTQZAQPFWMV-VAWYXSNFSA-N

物化性质

• 沸点：
  86-88 °C(Press: 7 Torr)
• 密度：
  0.775±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (E)-2-Methyl-1-(trimethylsilyl)oct-1-ene 、 碘 生成 (Z)-1-iodo-2-methyl-1-octene
  参考文献：
  名称：

  SNIDER B. B.; KARRAS M., J. ORGANOMETAL. CHEM., 1979, 179, NO 3, C37-C41

  摘要：

  DOI：
• 作为产物：
  描述：

  Trimethyl-(2-methyl-1-phenylsulfanyl-octyl)-silane 在 chloroamine-T 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以42%的产率得到(E)-2-Methyl-1-(trimethylsilyl)oct-1-ene
  参考文献：
  名称：

  Preparation of Alkylvinylsilanes via 1-Phenylchalcogeno-1-trimethylsilylalkanes

  摘要：

  DOI：

  10.1055/s-1983-30602

文献信息

• Photochemical Organocatalytic Regio‐ and Enantioselective Conjugate Addition of Allyl Groups to Enals
  作者：Martin Berger、Davide Carboni、Paolo Melchiorre

  DOI：10.1002/anie.202111648

  日期：2021.12.6

  The first catalytic enantioselective conjugate addition of allyl groups to α,β-unsaturated aldehydes is disclosed. The chemistry exploits the visible-light-excitation of chiral iminium ions to activate allyl silanes towards the formation of allylic radicals, which are then stereoselectively intercepted with high α-regioselectivity, complete chemoselectivity, and moderate to good enantioselectivity

  公开了烯丙基与 α,β-不饱和醛的第一次催化对映选择性共轭加成。该化学方法利用手性亚胺离子的可见光激发来活化烯丙基硅烷以形成烯丙基自由基，然后以高 α-区域选择性、完全化学选择性和中等至良好的对映选择性立体选择性拦截。
• The efficient method for the preparation of alkenylsilanes from organoaluminums
  作者：Rita N. Kadikova、Tat'yana P. Zosim、Usein M. Dzhemilev、Ilfir R. Ramazanov

  DOI：10.1016/j.jorganchem.2014.04.004

  日期：2014.8

  aluminacyclopentanes takes place on the less sterically hindered reaction center. Using electron-donating solvents (diethyl ether, THF) inhibits the reaction. A new convenient procedure of silylation was developed, which consists in obtaining the silyl tosylate by the reaction of chlorosilanes with anhydrous sodium tosylate in toluene solution. The resulting reaction mixture was reacted with organoaluminum compounds

  磺酸的甲硅烷基酯是用于β，β-和β-取代的1-烯基铝的便捷有效的甲硅烷基化剂。反应在室温下在CH 2 Cl 2中进行用己烷或己烷洗涤18小时，以高收率得到相应的烯基硅烷。同时，在所研究的反应中，α，β-二取代和α，β，β-三取代的1-烯基铝是惰性的。与氧化铝环戊-2-烯和氧化铝环戊烷的反应发生在空间位阻较小的反应中心上。使用供电子溶剂（乙醚，THF）会抑制反应。开发了一种新的便捷的甲硅烷基化方法，该方法包括通过氯硅烷与无水甲苯磺酸钠在甲苯溶液中的反应获得甲苯磺酸甲硅烷基酯。使所得反应混合物与有机铝化合物反应，而无需分离甲苯磺酸甲硅烷基酯。
• Pd-Catalyzed Coupling Reaction of Acetylenes, Iodotrimethylsilane, and Organozinc Reagents for the Stereoselective Synthesis of Vinylsilanes
  作者：Naoto Chatani、Nobuyoshi Amishiro、Takaya Morii、Toshiaki Yamashita、Shinji Murai

  DOI：10.1021/jo00111a048

  日期：1995.3

  The reaction of terminal acetylenes with Me(3)SiI (1) and organozinc reagents in the presence of Pd(PPh(3))(4) results in addition of the trimethylsilyl group of 1 and an alkyl group of the organozinc reagent to the acetylenes. In all cases the trimethylsilyl group adds to the terminal carbon of the acetylenes. Both aromatic and aliphatic terminal acetylenes undergo the coupling reaction with high regio- and stereoselectivities. The yield and stereoselectivity are relatively sensitive to the nature of the organozinc reagent used. The reaction of phenylacetylene (2) using Bu(2)Zn gives the corresponding coupling product in high yield with high stereoselectivity (>98%). In contrast, the use of BuZnI results in 92% stereoselectivity. The stereoselectivity for the reaction using (Me(3)-SiCH2)(2)Zn is lower than those for Me(2)Zn, Et(2)Zn, and Bu(2)Zn. For organozinc reagents, alkylzinc works well while phenyl-, ethynyl-, and allylzinc do not. The reaction using Me(3)SiCl, Me(3)SiBr, Me(3)SiSPh, Me(3)SiSePh, and Me(3)SiOTf in place of 1 does not proceed. The reaction with Me(3)SiMe(2)-SiI and Me(3)SiMe(2)SiMe(2)SiI in place of 1 gives the corresponding vinyldisilane and -trisilane, respectively.
• Nickel-catalyzed addition of Grignard reagents to silylacetylenes. Synthesis of tetrasubstituted alkenes
  作者：Barry B. Snider、Michael Karras、Robin S. E. Conn

  DOI：10.1021/ja00482a066

  日期：1978.7
• OGURA, FUMIO;OTSUBO, TETSUO;OHIRA, NORIYUKI;YAMAGUCHI, HACHIRO, SYNTHESIS, BRD, 1983, N 12, 1006-1008
  作者：OGURA, FUMIO、OTSUBO, TETSUO、OHIRA, NORIYUKI、YAMAGUCHI, HACHIRO

  DOI：——

  日期：——