(E)-2-trimethylsiloxy-4-phenyl-2-butene | 105881-89-8

• 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)-2-trimethylsiloxy-4-phenyl-2-butene
• 英文别名: (E)-3-(trimethylsiloxy)-1-phenyl-2-butene；trans-1-phenyl-3-trimethylsilyloxybut-2-ene；4-phenyl-2-(trimethylsilyl)oxy-2-butene；trimethyl-[(E)-4-phenylbut-2-en-2-yl]oxysilane
• CAS: 105881-89-8
• 化学式: C₁₃H₂₀OSi
• 分子量: 220.387
• InChiKey: LSXIWYOJDBSGMZ-ZRDIBKRKSA-N

物化性质

• 沸点：
  115-117 °C(Press: 5.5 Torr)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 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)-2-trimethylsiloxy-4-phenyl-2-butene 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-Phenyl-3-trimethylsilanyloxy-butan-2-one
  参考文献：
  名称：

  Studies on irreversible inhibition of serine proteases by α-sulfonyloxyketone derivatives

  摘要：

  alpha-Sulfonyloxyketone derivatives were found to be active-site directed irreversible inhibitors of serine proteases. (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00178-3
• 作为产物：
  描述：

  threo-1-phenyl-2-(phenylthio)-3-(trimethylsilyl)-3-butanol 在 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 生成 (E)-2-trimethylsiloxy-4-phenyl-2-butene
  参考文献：
  名称：

  Silyl ketone chemistry. Synthesis of regio- and stereoisomerically pure enol silyl ethers using .alpha.-phenylthio silyl ketones

  摘要：

  DOI：

  10.1021/jo00378a038

文献信息

• Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible-Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group
  作者：Naoto Esumi、Kensuke Suzuki、Yoshihiro Nishimoto、Makoto Yasuda

  DOI：10.1021/acs.orglett.6b02869

  日期：2016.11.4

  We report the visible-light-induced radical coupling reaction of silyl enol ethers with α-bromocarbonyl compounds to give 1,4-dicarbonyls. The reaction was effectively accelerated using an inexpensive organic dye (eosin Y) as a photoredox catalyst. 1,4-Dicarbonyl compounds alone were afforded, without the generation of carbonyl adducts of the α-halocarbonyls, which are usually generated in the presence

  我们报道了可见光诱导的甲硅烷基烯醇醚与α-溴羰基化合物的自由基偶联反应，得到1,4-二羰基。使用廉价的有机染料（曙红Y）作为光氧化还原催化剂可有效地促进反应。仅提供1，4-二羰基化合物，而没有生成α-卤代羰基的羰基加合物，α-卤代羰基的羰基加合物通常是在氟阴离子或路易斯酸的存在下生成的。将多种甲硅烷基烯醇醚，α-溴代酮，α-溴代酸酯和α-溴代酰胺应用于该系统以产生偶联化合物。
• 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。
• Regioselective Synthesis of Substituted (3E)-1,3-Dienes from Chelated Allyl-Ironcarbene Complexes and Potassium Enoxyborates
  作者：Jutta Böhmer、Frank Hampel、Rainer Schobert

  DOI：10.1055/s-1997-1394

  日期：1997.6

  The addition of potassium enoxyborates to the chelated allyl-iron-carbene complex 1 leads to the corresponding η 4-(3E)-1,3-diene complexes 2 in fair yields. Complexes 2 can be demetalated with ceric ammonium nitrate (CAN) to give unrearranged (3E)-t-oxo-1,3-dienes 3. Prior to decomplexation, the carbonyl group can be further modified. This is demonstrated by the syntheses of the natural terpene alcohol hotrienol and of a complexed methylene-separated dienyne. Potassium enoxyborates are superior to lithium enolates as they are readily prepared in situ from a variety of aldehydes and ketones which do not form sufficiently stable lithium derivatives. In contrast to lithium enolates, only C-C coupling products derived from the "kinetic" regioisomers are formed from unsymmetrical aliphatic ketones.

  将钾酯硼酸盐添加到螯合的烯丙基铁碳烯复合物1中，可以在合理产率下得到相应的 η 4-(3E)-1,3-二烯复合物2。复合物2可以用铈铵硝酸盐（CAN）去金属化，得到未重新排列的 (3E)-t-氧基-1,3-二烯3。在去复合之前，可以进一步修饰羰基。这通过合成天然萜醇霍特里诺尔和一种复合的亚甲基分隔的二炔来证明。钾酯硼酸盐优于锂烯醇盐，因为它们可以在多种不形成足够稳定的锂衍生物的醛和酮中原位制备。与锂烯醇盐相比，仅从不对称脂肪族酮中形成源自“动能”区域异构体的C-C偶联产物。
• 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。
• Regio- and stereoselective preparation of silyl enol ethers by alkylidenation of silyl esters
  作者：Kazuhiko Takai、Yasutaka Kataoka、Takashi Okazoe、Kiitiro Utimoto

  DOI：10.1016/0040-4039(88)85336-x

  日期：1988.1

  Treatment of trimethylsilyl esters with a reagent for alkylidenation of carbonyl groups derived from 1,1-dibromoalkane, zinc, TiCl4, and TMEDA in THF gives Z-trimethylsilyl enol ethers in a regio- and stereoselective manner.

  用一种试剂对三甲基甲硅烷基酯进行处理，以使其在THF中衍生自1,1-二溴代烷烃，锌，TiCl 4和TMEDA的羰基进行烷基化，从而制得Z-三甲基甲硅烷基烯醇醚。