(Z)-1,3-Diphenyl-5-trimethylsilanyloxy-hex-4-en-1-one | 100636-60-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-1,3-Diphenyl-5-trimethylsilanyloxy-hex-4-en-1-one
• 英文别名: (Z)-1,3-diphenyl-5-trimethylsilyloxyhex-4-en-1-one
• CAS: 100636-60-0
• 化学式: C₂₁H₂₆O₂Si
• 分子量: 338.522
• InChiKey: KIBKLNUWQCGGTM-ICFOKQHNSA-N

物化性质

• 沸点：
  425.3±45.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1,3-Diphenyl-5-trimethylsilanyloxy-hex-4-en-1-one 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 1,3-diphenyl-1,5-hexanedione
  参考文献：
  名称：

  A continuous Michael and aldol coupling of α,β-enones catalyzed by iridium complexes

  摘要：

  Ir[(COD)(PPh3)(2)]OTf activated by H-2 molecule catalyzes Michael-type coupling of alpha,beta-enones with enoxysilanes to give 1,5-dicarbonyl compounds after the subsequent protodesilylation. An identical catalyst system makes it possible to attain a continuous Michael and aldol modification toward alpha,beta-enones in a one-pot operation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02304-7
• 作为产物：
  描述：

  2-(三甲基硅氧基)丙烯 、 反式-查耳酮 在 [Ir(cod)(PPh₃)2]OTf 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 (Z)-1,3-Diphenyl-5-trimethylsilanyloxy-hex-4-en-1-one
  参考文献：
  名称：

  A continuous Michael and aldol coupling of α,β-enones catalyzed by iridium complexes

  摘要：

  Ir[(COD)(PPh3)(2)]OTf activated by H-2 molecule catalyzes Michael-type coupling of alpha,beta-enones with enoxysilanes to give 1,5-dicarbonyl compounds after the subsequent protodesilylation. An identical catalyst system makes it possible to attain a continuous Michael and aldol modification toward alpha,beta-enones in a one-pot operation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02304-7

文献信息

• Bismuth Trichloride as a New Efficient Catalyst in the Aldol Reaction and the Michael Reaction
  作者：Makoto Wada、Eiji Takeichi、Takashi Matsumoto

  DOI：10.1246/bcsj.64.990

  日期：1991.3

  In the presence of a catalytic amount of bismuth(III) trichloride (5 mol%), silyl enol ethers react with aldehydes at room temperature in dichloromethane to give the corresponding aldols in good yields. Silyl enol ethers also have been found to react with α,β-unsaturated ketones at room temperature in dichloromethane to afford the corresponding 1,5-dicarbonyl compounds, the Michael adducts in good

  在催化量的三氯化铋 (III) (5 mol%) 存在下，甲硅烷基烯醇醚在室温下在二氯甲烷中与醛反应，以良好的收率得到相应的醛醇。还发现甲硅烷基烯醇醚在室温下在二氯甲烷中与 α,β-不饱和酮反应，得到相应的 1,5-二羰基化合物，迈克尔加合物的产率很高。醛醇反应（甲硅烷基醚）和迈克尔反应（甲硅烷基烯醇醚）的中间加合物也以良好的产率获得。
• THE TRITYL PERCHLORATE CATALYZED MICHAEL REACTION
  作者：Shu Kobayashi、Masahiro Murakami、Teruaki Mukaiyama

  DOI：10.1246/cl.1985.953

  日期：1985.7.5

  In the presence of a catalytic amount of trityl perchlorate, 1,5-dicarbonyl compounds, the Michael adducts, are obtained in high yields by the reaction of silyl enol ethers with α,β-unsaturated ketones. The intermediate adducts, the synthetically valuable silyl enol ethers, are also isolated in high yields.

  在催化量的高氯酸三苯甲基酯存在下，通过甲硅烷基烯醇醚与 α,β-不饱和酮的反应，以高收率获得 1,5-二羰基化合物，即迈克尔加合物。中间加合物，具有合成价值的甲硅烷基烯醇醚，也以高产率分离。
• WADA, MAKOTO;TAKEICHI, EIJI;MATSUMOTO, TAKASHI, BULL. CHEM. SOC. JAP., 64,(1991) N, C. 990-994
  作者：WADA, MAKOTO、TAKEICHI, EIJI、MATSUMOTO, TAKASHI

  DOI：——

  日期：——