(Z)-trimethyl(2-phenylbut-1-en-1-yl)silane | 68669-61-4

• 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: (Z)-trimethyl(2-phenylbut-1-en-1-yl)silane
• 英文别名: trimethyl-[(Z)-2-phenylbut-1-enyl]silane
• CAS: 68669-61-4
• 化学式: C₁₃H₂₀Si
• 分子量: 204.387
• InChiKey: GGIOMPAPWBRYJM-QXMHVHEDSA-N

物化性质

• 沸点：
  244.9±10.0 °C(Predicted)
• 密度：
  0.867±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 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

• 作为产物：
  描述：

  (E)-trimethyl(2-phenylbut-1-en-1-yl)silane 在 C₃₂H₂₈N₂O₅ 作用下， 以 乙腈 为溶剂， 以72 %的产率得到(Z)-trimethyl(2-phenylbut-1-en-1-yl)silane
  参考文献：
  名称：

  Self-assembly of benzophenone-diphenylalanine conjugate into a nanostructured photocatalyst

  摘要：

  光活性二苯甲酮与二苯基丙氨酸共轭产生了一种自组装光催化剂，并在二苯乙烯衍生物的 E → Z 光异构化过程中进行了探究。

  DOI：

  10.1039/d3cc01673k

文献信息

• Geometric <i>E</i> → <i>Z</i> Isomerisation of Alkenyl Silanes by Selective Energy Transfer Catalysis: Stereodivergent Synthesis of Triarylethylenes via a Formal <i>anti</i> ‐Metallometallation
  作者：Svenja I. Faßbender、John J. Molloy、Christian Mück‐Lichtenfeld、Ryan Gilmour

  DOI：10.1002/anie.201910169

  日期：2019.12.16

  An efficient geometrical E→Z isomerisation of alkenyl silanes is disclosed via selective energy transfer using an inexpensive organic sensitiser. Characterised by operational simplicity, short reaction times (2 h), and broad substrate tolerance, the reaction displays high selectivity for trisubstituted systems (Z/E up to 95:5). In contrast to thermal activation, directionality results from deconjugation

  通过使用廉价的有机敏化剂的选择性能量转移，公开了烯基硅烷的有效几何E→Z异构化。该反应的特点是操作简便，反应时间短（2小时）和广泛的底物耐受性，该反应对三取代系统显示出高选择性（Z / E高达95：5）。与热激活相反，方向​​性是由于A1,3-应变导致Z异构体中的π系统解共轭，从而抑制了再激活。β取代基的结构重要性从逻辑上促进了对混合双亲核试剂（Si，Sn，B）的研究。这些多用途的关键销钉也易于异构化，从而实现了正式的抗金属金属化。机械询问，在理论研究的支持下，
• Yttrium-Mediated Conversion of Vinyl Grignard Reagent to a 1,2-Dimetalated Ethane and Its Synthetic Application
  作者：Ryoichi Tanaka、Hiroaki Sanjiki、Hirokazu Urabe

  DOI：10.1021/ja077992u

  日期：2008.3.1

  ethane was generated from a vinyl Grignard reagent in the presence of yttrium(III) chloride, sodium cyclopentadienide, and diisobutylaluminum hydride (Dibal). This reagent enables the regio- and stereoselective (metaloethyl)metalation of acetylenes to produce ethylated alkenes after hydrolysis. In addition to simple hydrolysis, further carbon−carbon bond formation or functionalization at the metaloethyl

  在氯化钇 (III)、环戊二烯化钠和二异丁基氢化铝 (Dibal) 存在下，由乙烯基格利雅试剂生成新的 1,2-二金属化乙烷。该试剂能够使乙炔进行区域和立体选择性（金属乙基）金属化，从而在水解后生成乙基化烯烃。除了简单的水解外，金属乙基上的进一步碳-碳键形成或官能化是可能的，这表明基于钇的 1,2-二金属乙烷可用作结合试剂。此外，该试剂的反应性双碳阴离子特性可通过连续双羰基加成从酯中一锅法合成环丙醇。
• Photocatalytic <i>E</i> → <i>Z Contra</i> ‐Thermodynamic Isomerization of Vinyl Silanes with Lewis Base
  作者：Thi Minh Thi Le、Thibaud Brégent、Philippe Jubault、Thomas Poisson

  DOI：10.1002/chem.202201514

  日期：2022.9.16

  The contra-thermodynamic E→Z isomerization of vinyl silanes was reported using rac-BINAP as the photocatalyst. This reaction proceeds via the in situ formation of a chromophoric species, in the presence of catalyst. Under irradiation at 405 nm the interconversion of E-isomers into the Z-congeners were carried out in good to excellent yields and outstanding Z/E selectivities (18 examples) and the reaction

  使用rac -BINAP 作为光催化剂报道了乙烯基硅烷的逆热力学E → Z异构化。该反应在催化剂存在下通过发色物质的原位形成进行。在 405 nm 的照射下，E异构体向 Z 同系物的相互转化以良好至极好的产率和出色的Z / E选择性（18 个实施例）进行，并研究了反应机理。
• A nickel-catalyzed carbozincation of aryl-substituted alkynes
  作者：Thomas Stüdemann、Malika Ibrahim-Ouali、Paul Knochel

  DOI：10.1016/s0040-4020(97)10226-5

  日期：1998.2

  The addition of dialkylzincs or diphenylzinc to substituted phenylacetylenes in the presence of catalytic amounts of Ni(acac)(2) in THF : NMP mixtures produces syn-carbozincation products with good to excellent regio-and stereoselectivity. After quenching with an electrophile (iodine, acyl chloride, allyl bromide) tetrasubstituted olefines are obtained in good to satisfactory yields. An intramolecular version of the reaction is possible using a terminal triple bond bearing an iodine at a remote position. More substituted iodo-alkynes furnish only reductive elimination products. An application to a stereoselective synthesis of (Z)-tamoxifen (Z: E > 99: 1) has been developed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Wong, Ken-Tsung; Ni, Zhi-Jie; Luh, Tien-Yau, Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3113 - 3116
  作者：Wong, Ken-Tsung、Ni, Zhi-Jie、Luh, Tien-Yau

  DOI：——

  日期：——