phenyl-3 trimethylsilyloxy-1 propene-1 (Z) | 51425-56-0

• 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: phenyl-3 trimethylsilyloxy-1 propene-1 (Z)
• 英文别名: trimethyl[(Z)-(3-phenyl-1-propenyl)oxy]silane；(Z)-dihydrocinnamaldehyde trimethyl silyl enol ether；(Z)-1-trimethylsiloxy-3-phenyl-1-propene；(Z)-3-phenyl-1-propenyl trimethylsilyl ether；trimethyl{[(Z)-3-phenylprop-1-en-1-yl]oxy}silane；trimethyl((3-phenylprop-1-en-1-yl)oxy)silane；trimethyl-[(Z)-3-phenylprop-1-enoxy]silane
• CAS: 51425-56-0
• 化学式: C₁₂H₁₈OSi
• 分子量: 206.36
• InChiKey: WUHUHUMCBUSVCX-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  threo-1-phenyl-2-(phenylthio)-3-(trimethylsilyl)-3-butanol 、 甲基锂 生成 phenyl-3 trimethylsilyloxy-1 propene-1 (Z)
  参考文献：
  名称：

  REICH, HANS J.;HOLTAN, RONALD C.;BOLM, CARSTEN, J. AMER. CHEM. SOC., 112,(1990) N4, C. 5609-5617

  摘要：

  DOI：

文献信息

• Facile synthesis of silyl enol ethers by Mg-promoted coupling of aliphatic carbonyl compounds with trimethylsilyl chloride
  作者：Yoshio Ishino、Yoshio Kita、Hirofumi Maekawa、Toshinobu Ohno、Yasuhiro Yamasaki、Toshiyuki Miyata、Ikuzo Nishiguchi

  DOI：10.1016/s0040-4039(98)02659-8

  日期：1999.2

  Treatment of aliphatic carbonyl compounds with trimethylsilyl chloride with Mg turning for Grignard reaction without any pre-treatment in N,N-dimethylformamide at room temperature brought about highly facile, effective and stereoselective coupling to give the corresponding silyl enol ethers in good yields.

  在室温下，在N，N-二甲基甲酰胺中不进行任何预处理的情况下，用三甲基甲硅烷基氯将镁转为格氏反应来处理脂族羰基化合物，可实现高度简便，有效和立体选择性的偶联，从而以良好的收率得到相应的甲硅烷基烯醇醚。
• Electrophilic Trifluoromethylthiolation of Carbonyl Compounds
  作者：Sébastien Alazet、Luc Zimmer、Thierry Billard

  DOI：10.1002/chem.201403409

  日期：2014.7.7

  prefunctionalization, has been developed. Aldehydes, ketones, esters, amides, keto‐esters, alkaloids, and steroids have been trifluoromethylthiolated with good yields. This work, proposing a new reagent for electrophilic trifluoromethylthiolation, provides a route towards the original synthesis of various trifluoromethylthiolated molecules for further applications.

  已开发出无需预官能化即可对羰基化合物进行α-三氟甲基硫醇化的通用方法。醛，酮，酯，酰胺，酮酸酯，生物碱和类固醇已被三氟甲基硫醇化，收率良好。这项工作提出了一种新的亲电子三氟甲基硫醇化试剂，为进一步合成各种三氟甲基硫醇化分子提供了一条途径。
• Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3‐Metalate Rearrangement of Lithium Enolates
  作者：Yue Hu、Wei Sun、Tao Zhang、Nuo Xu、Jianeng Xu、Yu Lan、Chao Liu

  DOI：10.1002/anie.201909235

  日期：2019.10.28

  unprecedented stereoselective synthesis of trisubstituted vinylboronates is reported to proceed by direct borylation of lithium ketone enolates under transition-metal-free conditions. The stereospecific C-O borylation of lithium enolates was triggered by a carbonyl-induced 1,3-metalate rearrangement via a C-bound boron enolate. DFT calculations and control experiments revealed that the stereoselectivity is controlled

  据报道，通过在无过渡金属的条件下直接酮化锂酮烯醇盐进行三取代乙烯基硼酸酯的空前的立体选择性合成。烯醇酸锂的立体有择CO硼化反应是通过C结合的硼烯醇盐由羰基诱导的1,3-金属盐重排触发的。DFT计算和控制实验表明，立体选择性受空间位阻的控制。使用新开发的方法可以方便地合成各种立体有择的三取代乙烯基硼酸酯，以及几种四取代乙烯基硼酸酯。基于立体定向乙烯基硼酸酯的转化，有效地获得了烯雌酚的单一异构体。
• Me3SiCl/HMPA accelerated conjugate addition of catalytic copper reagent. Stereoselective synthesis of enol silyl ether of aldehyde
  作者：Yoshiaki Horiguchi、Satoshi Matsuzawa、Eiichi Nakamura、Isao Kuwajima

  DOI：10.1016/s0040-4039(00)84901-1

  日期：1986.1

  Copper-catalyzed conjugate addition of the Grignard reagents in the presence of Me3SiCl and HMPA proceeds in much higher yield than the reaction of conventional organocopper reagents and shows very good regio-, stereo-, and chemoselectivities.

  在Me 3 SiCl和HMPA存在下，格氏试剂的铜催化共轭加成比常规有机铜试剂的反应收率高得多，并且显示出非常好的区域选择性，立体选择性和化学选择性。
• Chlorosilane-accelerated conjugate addition of catalytic and stoichiometric organocopper reagents
  作者：Satoshi Matsuzawa、Yoshiaki Horiguchi、Eiichi Nakamura、Isao Kuwajima

  DOI：10.1016/0040-4020(89)80064-x

  日期：1989.1

  Trialkylsilyl chlorides, particularly in combination with hexamethylphosphoramide or 4-dimethylaminopyridine, dramatically accelerates the conjugate addition of catalytic and stoichiometric organocopper reagents onto enones, enals, and enoates, in which very high degrees of stereo- and chemoselectivities were observed.

  三烷基甲硅烷基氯化物，特别是与六甲基磷酰胺或4-二甲基氨基吡啶组合，可显着加速催化和化学计量的有机铜试剂在烯酮，烯醛和烯酸酯上的共轭加成，其中观察到很高的立体和化学选择性。