(E)-(isopropoxy)dimethyl(styryl)silane | 202933-51-5

• 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)-(isopropoxy)dimethyl(styryl)silane
• 英文别名: dimethyl-[(E)-2-phenylethenyl]-propan-2-yloxysilane
• CAS: 202933-51-5
• 化学式: C₁₃H₂₀OSi
• 分子量: 220.387
• InChiKey: BSHTZZNPGDPVRA-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  15
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-(isopropoxy)dimethyl(styryl)silane 在 lithium aluminium tetrahydride 作用下， 以 苯 为溶剂， 反应 18.0h， 以75%的产率得到β-styryldimethylsilane
  参考文献：
  名称：

  A general synthesis of vinylic silyl hydrides using nickel catalysis. Applications to the syntheses of silylene-tethered conjugated polymers

  摘要：

  Treatment of benzylic or allylic dithioacetals with Me-2((PrO)-Pr-i)SiCH2MgCl in the presence of NiCl2(PPh3)(2) catalyst yielded the corresponding i-propoxy(vinyl)silanes which are reduced with LIAlH4, to afford vinylic silyl hydrides. These hydrides serve as the precursors for the syntheses of silylene-tethered sigma,pi-conjugated copolymers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10218-6
• 作为产物：
  描述：

  苯乙烯 在 二氯化双(三环己基膦)镍(II) 、 三甲基铝 、 三乙胺 作用下， 以 1,4-二氧六环 、 正己烷 为溶剂， 反应 19.0h， 生成 (E)-(isopropoxy)dimethyl(styryl)silane
  参考文献：
  名称：

  氯硅烷的直接甲硅烷基-Heck反应

  摘要：

  镍配合物/路易斯酸的组合有效地催化了氯硅烷的直接甲硅烷基-Heck反应，氯硅烷是有机硅工业的关键原料，可提供合成上重要的烯基硅烷产品。三氯硅烷，二氯硅烷和一氯硅烷经过甲硅烷基-Heck反应，以高收率得到相应的烯基硅烷。在二氯硅烷的反应中，发生一次取代以高度选择性的方式得到单烯基硅烷。

  DOI：

  10.1021/acs.orglett.8b00847

文献信息

• Preparation of Vinyl Silyl Ethers and Disiloxanes via the Silyl-Heck Reaction of Silyl Ditriflates
  作者：Sara E. S. Martin、Donald A. Watson

  DOI：10.1021/ja407748z

  日期：2013.9.11

  Vinyl silyl ethers and disiloxanes can now be prepared from aryl-substituted alkenes and related substrates using a silyl-Heck reaction. The reaction employs a commercially available catalyst system and mild conditions. This work represents a highly practical means of accessing diverse classes of vinyl silyl ether substrates in an efficient and direct manner with complete regiomeric and geometric selectivity

  现在可以使用甲硅烷基-Heck 反应从芳基取代的烯烃和相关底物制备乙烯基甲硅烷基醚和二硅氧烷。该反应采用市售的催化剂体系和温和的条件。这项工作代表了一种非常实用的方法，可以以有效和直接的方式获得不同类别的乙烯基甲硅烷基醚底物，并具有完全的区域异构和几何选择性。
• Synthesis and Photophysical Studies of Silylene-Spaced Divinylarene Copolymers. Molecular Weight Dependent Fluorescence of Alternating Silylene−Divinylbenzene Copolymers
  作者：Ruey-Min Chen、Kuo-Ming Chien、Ken-Tsung Wong、Bih-Yaw Jin、Tien-Yau Luh、Jui-Hung Hsu、Wunshain Fann

  DOI：10.1021/ja971373b

  日期：1997.11.1
• Norbornadiene as an Efficient Hydrogen Scavenger for the Palladium-Catalyzed Conversion of Hydrosilanes to Alkoxysilanes
  作者：Sundarraj Sudhakar、Tien-Yau Luh

  DOI：10.1021/jo025886z

  日期：2002.9.1

  A palladium-catalyzed mild and efficient method for the alcoholysis of hydrosilanes containing a C=C bond in the presence of norbornadiene (NBD) is reported. The highly strained NBD acts as a hydrogen scavenger, which abstracts the hydrogen produced during the process, protecting the C=C bond from being hydrogenated.
• A general synthesis of vinylic silyl hydrides using nickel catalysis. Applications to the syntheses of silylene-tethered conjugated polymers
  作者：Ruey-Min Chen、Tien-Yau Luh

  DOI：10.1016/s0040-4020(97)10218-6

  日期：1998.2

  Treatment of benzylic or allylic dithioacetals with Me-2((PrO)-Pr-i)SiCH2MgCl in the presence of NiCl2(PPh3)(2) catalyst yielded the corresponding i-propoxy(vinyl)silanes which are reduced with LIAlH4, to afford vinylic silyl hydrides. These hydrides serve as the precursors for the syntheses of silylene-tethered sigma,pi-conjugated copolymers. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Direct Silyl–Heck Reaction of Chlorosilanes
  作者：Kazuhiro Matsumoto、Jiadi Huang、Yuki Naganawa、Haiqing Guo、Teruo Beppu、Kazuhiko Sato、Shigeru Shimada、Yumiko Nakajima

  DOI：10.1021/acs.orglett.8b00847

  日期：2018.4.20

  effectively catalyzed the direct silyl–Heck reaction of chlorosilanes, which are key raw materials in the organosilicon industry, to give synthetically important alkenylsilane products. Trichlorosilanes, dichlorosilanes, and monochlorosilanes underwent the silyl–Heck reaction to afford the corresponding alkenylsilanes in high yields. In the reactions of dichlorosilanes, a single substitution occurred to give

  镍配合物/路易斯酸的组合有效地催化了氯硅烷的直接甲硅烷基-Heck反应，氯硅烷是有机硅工业的关键原料，可提供合成上重要的烯基硅烷产品。三氯硅烷，二氯硅烷和一氯硅烷经过甲硅烷基-Heck反应，以高收率得到相应的烯基硅烷。在二氯硅烷的反应中，发生一次取代以高度选择性的方式得到单烯基硅烷。