(Z)-dimethyl(1-phenylprop-1-enyloxy)silane | 207446-10-4

• 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)-dimethyl(1-phenylprop-1-enyloxy)silane
• 英文别名: (Z)-1-dimethylsiloxy-1-phenyl-1-propene；dimethyl-[(Z)-1-phenylprop-1-enoxy]silane
• CAS: 207446-10-4
• 化学式: C₁₁H₁₆OSi
• 分子量: 192.333
• InChiKey: NWKOSZXWEHUEDG-WCIBSUBMSA-N

物化性质

• 沸点：
  247.5±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (Z)-dimethyl(1-phenylprop-1-enyloxy)silane 在 盐酸 、 magnesium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.08h， 生成 1,5-Pentanedione, 2,3-dimethyl-1,5-diphenyl-, (R*,S*)-
  参考文献：
  名称：

  氯化镁促进二甲基甲硅烷基烯醇化物与α-烯酮的迈克尔加成

  摘要：

  在 MgCl 2 存在下，二甲基甲硅烷基 (DMS) 烯醇化物 1 与 DMF 中的 α-烯酮顺利反应，以中等至高产率形成 1,5-二酮 3。迈克尔加成以中等至高的反非对映选择性进行。

  DOI：

  10.1055/s-2003-41467
• 作为产物：
  描述：

  二甲基一氯硅烷 、 苯丙酮 在 lithium diisopropyl amide 作用下， 生成 dimethyl-[(E)-1-phenylprop-1-enoxy]silane 、 (Z)-dimethyl(1-phenylprop-1-enyloxy)silane
  参考文献：
  名称：

  Uncatalyzed aldol reaction using a dimethylsilyl enolate and α-dimethylsilyl ester in N,N-dimethylformamide

  摘要：

  Dimethylsilyl enolates and alpha-dimethylsilyl esters reacted with aldehydes in N,N-dimethyl-formamide without an activator to give aldol adducts in moderate to good yields. Under the same conditions, the corresponding trimethylsilyl derivatives exhibited lower reactivities toward the aldol reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00275-5

文献信息

• Efficient Mannich Reaction Using Iminium Salts Generated from Glycine Derivatives
  作者：Makoto Shimizu、Toshiki Kusunoki、Mari Yoshida、Koichi Kondo、Isao Mizota

  DOI：10.1246/cl.2011.351

  日期：2011.4.5

  Iminium salts generated by the oxidation of amino ketene silyl acetals underwent a facile Mannich reaction with another ketene silyl acetal to give aspartic acid derivatives in good yields. The dia...

  由氨基烯酮甲硅烷基缩醛氧化生成的亚胺盐与另一种烯酮甲硅烷基缩醛进行简单的曼尼希反应，以良好的收率得到天冬氨酸衍生物。日...
• Scandium(III) Fluoride as a Novel Catalyst for Hydroxymethylation of Dimethylsilyl Enolates in Aqueous Media
  作者：Shu Kobayashi、Masaya Kokubo

  DOI：10.1055/s-2008-1078409

  日期：2008.6

  Hydroxymethylation of dimethylsilyl (DMS) enolates using aqueous formaldehyde solution is catalyzed by scandium(III) fluoride (ScF3) in aqueous media to give the corresponding β-hydroxy ketones in good to excellent yields. Whilst the DMS enolate reactions are facile the TMS enolates react sluggishly under the same conditions. ScF3 has been shown to be a unique catalyst for this reaction.

  氟化钪（ScF3）在水介质中催化甲醛水溶液对二甲基硅烷基（DMS）烯醇酸盐的羟甲基化反应，可以得到相应的δ-羟基酮，收率良好甚至极佳。在相同条件下，DMS 烯醇反应容易，而 TMS 烯醇反应缓慢。研究表明，ScF3 是该反应的一种独特催化剂。
• Tandem Aldol-Reduction Reaction of Dimethylsilyl Enolates: A New Method for Stereoselective Preparation of 1,3-Diols
  作者：Katsukiyo Miura、Takahiro Nakagawa、Shuntaro Suda、Akira Hosomi

  DOI：10.1246/cl.2000.150

  日期：2000.2

  derived from acyclic ketones reacted with aldehydes to give syn,syn-1,3-diols 7a and 8a with moderate to high diastereoselectivity. The stereochemical outcome can be attributed to a syn-selective aldol reaction and the subsequent 1,2-syn-selective intramolecular reduction.

  在催化量的 TBAF (Bu4NF) 存在下，衍生自无环酮的二甲基甲硅烷基烯醇化物与醛反应，得到具有中高非对映选择性的 syn,syn-1,3-二醇 7a 和 8a。立体化学结果可归因于顺式选择性羟醛反应和随后的 1,2-顺式选择性分子内还原。
• Lewis Base-Promoted Aldol Reaction of Dimethylsilyl Enolates in Aqueous Dimethylformamide:  Use of Calcium Chloride as a Lewis Base Catalyst
  作者：Katsukiyo Miura、Takahiro Nakagawa、Akira Hosomi

  DOI：10.1021/ja017218l

  日期：2002.1.1

  In the presence of CaCl2, dimethylsilyl (DMS) enolates smoothly reacted with aldehydes under mild conditions to give aldol adducts in good to high yields. The catalytic activities of various metal and tetrabutylammonium salts have revealed that CaCl2 works as a Lewis base catalyst to activate DMS enolates. The CaCl2-promoted reaction proceeded even in the presence of water or in pure water. This catalytic system was applicable to the aldol reaction with aqueous aldehydes such as formalin.
• Uncatalyzed aldol reaction using a dimethylsilyl enolate and α-dimethylsilyl ester in N,N-dimethylformamide
  作者：Katsukiyo Miura、Hiroshi Sato、Kentaro Tamaki、Hajime Ito、Akira Hosomi

  DOI：10.1016/s0040-4039(98)00275-5

  日期：1998.4

  Dimethylsilyl enolates and alpha-dimethylsilyl esters reacted with aldehydes in N,N-dimethyl-formamide without an activator to give aldol adducts in moderate to good yields. Under the same conditions, the corresponding trimethylsilyl derivatives exhibited lower reactivities toward the aldol reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.