(E)-trimethyl(4-phenylbut-1-en-1-yl)silane | 88261-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-trimethyl(4-phenylbut-1-en-1-yl)silane
• 英文别名: (E)-trimethyl(4-phenylbut-1-enyl)silane；Trimethyl((E)-4-phenyl-1-butenyl)silane；trimethyl[(E)-4-phenyl-1-butenyl]silane；(E)-4-phenyl-1-trimethylsilylbut-1-ene；(E)-4-phenyl-1-(trimethylsilyl)but-1-ene；trimethyl-[(E)-4-phenylbut-1-enyl]silane
• CAS: 88261-98-7
• 化学式: C₁₃H₂₀Si
• 分子量: 204.387
• InChiKey: FUFQVHSRYMZEOG-XYOKQWHBSA-N

物化性质

• 沸点：
  92-94 °C(Press: 1.0 Torr)
• 密度：
  0.872±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  14
• 可旋转键数：
  4
• 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：

  (E)-trimethyl(4-phenylbut-1-en-1-yl)silane 在 (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene 、 sodium peroxoborate tetrahydrate 、 potassium tert-butylate 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.5h， 生成 (S)-4-phenyl-1-(trimethylsilyl)butan-2-ol
  参考文献：
  名称：

  电子键合手性膦-铜（I）配合物催化烯基硅烷的区域和对映选择性单硼化

  摘要：

  AbstractAn asymmetric monoborylation of alkenylsilanes catalyzed by a copper(I) complex with the chiral bisphosphine ligand BenzP* is reported. The reaction proceeded with excellent regioselectivity and high enantioselectivity to afford the corresponding optically active organoboronate esters with a stereogenic CB bond containing a vicinal silyl group. The synthetic utility of the product is demonstrated through stepwise transformations to multifunctional optically active compounds in a stereospecific manner.magnified image

  DOI：

  10.1002/adsc.201300765
• 作为产物：
  描述：

  (Z)-trimethyl(4-phenylbut-1-en-1-yl)silane 在 三正丁基氢锡 作用下， 生成 (E)-trimethyl(4-phenylbut-1-en-1-yl)silane
  参考文献：
  名称：

  电子键合手性膦-铜（I）配合物催化烯基硅烷的区域和对映选择性单硼化

  摘要：

  AbstractAn asymmetric monoborylation of alkenylsilanes catalyzed by a copper(I) complex with the chiral bisphosphine ligand BenzP* is reported. The reaction proceeded with excellent regioselectivity and high enantioselectivity to afford the corresponding optically active organoboronate esters with a stereogenic CB bond containing a vicinal silyl group. The synthetic utility of the product is demonstrated through stepwise transformations to multifunctional optically active compounds in a stereospecific manner.magnified image

  DOI：

  10.1002/adsc.201300765

文献信息

• Rhodium-Catalyzed Acylation of Vinylsilanes with Acid Anhydrides
  作者：Motoki Yamane、Kazuyoshi Uera、Koichi Narasaka

  DOI：10.1246/bcsj.78.477

  日期：2005.3

  A catalytic acylation of vinylsilane with acid anhydride is accomplished by the use of [RhCl(CO)2]2, in which the transmetalation between vinylsilane and rhodium(I) carbonyl complex plays a key rol...

  乙烯基硅烷与酸酐的催化酰化是通过使用 [RhCl(CO)2]2 完成的，其中乙烯基硅烷和铑（I）羰基配合物之间的金属转移起着关键作用...
• Reactions of vinylsilanes with lewis acid-activated iodosylbenzene: stereospecific syntheses of vinyliodonium tetrafluoroborates and their reactions as highly activated vinyl halides
  作者：Masahito Ochiai、Kenzo Sumi、Yoshikazu Takaoka、Munetaka Kunishima、Yoshimitsu Nagao、Motoo Shiro、Eiichi Fujita

  DOI：10.1016/s0040-4020(01)86659-x

  日期：1988.1

  salts behave like the highly activated species of vinyl iodides due to the high leaving ability of the iodine(III) substituents. Thus, a variety of substituted olefins including α-cyano and α-nitro olefins, vinyl sulfides, vinyl halides, and α,β-unsaturated esters, were synthesized from under mild conditions. A ligand coupling mechanism via the formation of 10-I-3 intermediate containing a copper(III)

  烯基（苯基）碘化四氟硼酸酯是通过烯基硅烷与碘基苯和三氟化硼-二乙醚或四氟硼酸三乙基氧鎓反应而合成的。反应立体定向进行，保留了α-环糊精的结构。（4-叔丁基环己烯基）苯基碘鎓四氟硼酸盐（）的X射线衍射分析显示，T形排列扭曲的高离子结构。由于碘（III）取代基的高离去能力，碘鎓盐的行为类似于高度活化的乙烯基碘。因此，合成了包括α-氰基和α-硝基烯烃，乙烯基硫化物，乙烯基卤化物和α，β-不饱和酯在内的各种取代烯烃。在温和的条件下。提出了通过形成含有铜（III）配体的10-I-3中间体的配体偶联机理，以用亲核试剂取代。
• Alkylidenation of Carbonyl Compounds with <i>gem</i>-Dizincioalkanes Mediated with Titanium Dichloride
  作者：Seijiro Matsubara、Tsuyoshi Mizuno、Tasuyuiki Otake、Masami Kobata、Kiitiro Utimoto、Kazuhiko Takai

  DOI：10.1055/s-1998-1980

  日期：1998.12

  Olefination of carbonyl compounds with gem-dizincioalkanes, bis(iodozincio)methane, 1,1-bis(iodozincio)ethane, and bis(bromozincio)methyltrimethylsilane, afforded the corresponding olefins in good to excellent yields.

  用gem-二锌烷、双(碘锌)甲烷、1,1-双(碘锌)乙烷和双(溴锌)甲基三甲基硅烷对羰基化合物进行烯烃化，得到相应的烯烃，产率良好到优异。
• Intramolecular aromatic cyclizations of alkenyliodonium tetrafluoroborates
  作者：Masahito Ochiai、Yoshikazu Takaoka、Kenzo Sumi、Yoshimitsu Nagao

  DOI：10.1039/c39860001382

  日期：——

  1,2-Dihydronaphthalene and 2H-chromene derivatives have been synthesized by thermal intramolecular cyclizations of alkenyliodonium tetrafluoroborates under mild reaction conditions.

  通过在温和的反应条件下对四氟硼酸烯基碘鎓的分子内热环化反应合成了1,2-二氢萘和2 H-色烯衍生物。
• Transformation of Aldehydes into (<i>E</i>)-1-Alkenylsilanes and (<i>E</i>)-1-Alkenylboronic Esters with a Catalytic Amount of a Chromium Salt
  作者：Kazuhiko Takai、Yuji Kunisada、Yukiko Tachibana、Nana Yamaji、Emi Nakatani

  DOI：10.1246/bcsj.77.1581

  日期：2004.8

  (Diiodomethyl)trimethylsilane (Me3SiCHI2, 1) is produced by treatment of iodoform with manganese in the presence of Me3SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereosel...

  (二碘甲基)三甲基硅烷 (Me3SiCHI2, 1) 是通过在 Me3SiCl 存在下用锰处理碘仿来生产的。醛在立体定向中转化为 (E)-1-三甲基甲硅烷基-1-烯烃...