4-silyloxy-3-ethylpent-3-en-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-silyloxy-3-ethylpent-3-en-2-one
• 英文别名: (Z)-3-ethyl-4-trimethylsilyloxypent-3-en-2-one
• 化学式: C₁₀H₂₀O₂Si
• 分子量: 200.353
• InChiKey: GABIBNAWKNRZOU-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 、 4-silyloxy-3-ethylpent-3-en-2-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到methyl 3-ethyl-6-hydroxy-2,4-dimethylbenzoate
  参考文献：
  名称：

  基于“ [3 + 3]环化/铃木交叉偶联/ Friedel-Crafts酰化”策略的芴酮合成

  摘要：

  通过顺序的“ [3 + 3]环化-Suzuki交叉偶联/ Friedel-Crafts酰化”反应制备功能化的芴酮。

  DOI：

  10.1016/j.tetlet.2006.07.025

文献信息

• Synthesis of 3-Alkyl- and 3-Chloroalkyl-2-hydroxybenzoates Based on [3+3] Cyclizations of 4-Alkyl- and 4-Chloroalkyl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes
  作者：Peter Langer、Van Thi Nguyen、Esen Bellur、Bettina Appel

  DOI：10.1055/s-2006-926381

  日期：——

  The TiCl 4 -mediated [3+3] cyclization of 4-alkyl- and 4-chloroalkyl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes with 3-silyl-alk-2-en- 1-ones afforded 3-alkyl- and 3-chloroalkyl-2-hydroxybenzoates, respectively; the latter containing a remote chloride functionality. The TiCl 4 - and TiBr 4 -mediated [3+3] cyclization of 1,3-bis(trimethylsilyloxy)-4-chloroalkylbuta-1,3-dienes with 1,1-diacetylcyclopropane

  TiCl 4 介导的 [3+3] 环化 4-烷基-和 4-氯烷基-1,3-双(三甲基甲硅烷氧基)丁-1,3-二烯与 3-甲硅烷基-烷-2-烯-1-酮分别得到3-烷基-和3-氯烷基-2-羟基苯甲酸酯；后者包含远程氯化物功能。TiCl 4 - 和TiBr 4 介导的1,3-双(三甲基甲硅烷氧基)-4-氯烷基丁-1,3-二烯与1,1-二乙酰环丙烷的[3+3] 环化反应得到含有两个远程卤化物官能团的水杨酸盐。
• The first 4-chloro-1,3-bis(trimethylsilyloxy)-1,3-diene and its application to the regioselective synthesis of chlorinated arenes
  作者：Stefanie Reim、Peter Langer

  DOI：10.1016/j.tetlet.2008.01.139

  日期：2008.3

  Chlorinated phenols, benzophenones, and butenolides are prepared by various one-pot cyclization reactions of the first 4-chloro-1,3-bis(trimethylsilyloxy)-1,3-butadiene.

  氯化苯酚，二苯甲酮和丁烯内酯是通过对第一个4-氯-1,3-双（三甲基甲硅烷氧基）-1,3-丁二烯进行单锅环化反应制得的。
• Synthesis of chromanes by sequential ‘[3+3]-cyclization/Williamson’ reactions of 1,3-bis(trimethylsilyloxy)-7-chlorohepta-1,3-dienes
  作者：Van Thi Hong Nguyen、Bettina Appel、Peter Langer

  DOI：10.1016/j.tet.2006.05.076

  日期：2006.8

  Functionalized chromanes were prepared by sequential '[3+3]-cyclization/Williamson' reactions of 1,3-bis(trimethylsilyloxy)-7-chlorohepta-1,3-dienes with 1,1,3,3-tetrametboxypropane, 3-silyloxyalk-2-en-1-ones, and 1,1-diacetylcyclopropane. The first step of the sequence involves [3+3] cyclizations of the starting materials to give 2-(3-chloropropyl)phenols. The subsequent cyclization proceeds by intramolecular nucleophilic substitution. 6-(2-Hydroxybenzoyl)chromanes were prepared based on sequential '[3+3]-cyclization/Williamson' reactions of 1,3-bis(trimethylsilyloxy)-7-chlorohepta-1,3-dienes with 3-formylchromones. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of dibenzo[b,d]pyran-6-ones based on a ‘[3+3] cyclization–Suzuki cross-coupling’ strategy
  作者：Van Thi Hong Nguyen、Peter Langer

  DOI：10.1016/j.tetlet.2004.12.030

  日期：2005.2

  Functionalized dibenzo[b,d]pyran-6-ones were prepared by sequential '[3+3] cyclization-Suzuki cross-coupling' reactions. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of functionalized benzopyrans by sequential [3+3]-cyclization—Williamson reactions of 1,3-bis(trimethylsilyloxy)-7-chlorohepta-1,3-dienes
  作者：Van Thi Hong Nguyen、Peter Langer

  DOI：10.1016/j.tetlet.2004.12.009

  日期：2005.1

  Functionalized benzopyrans were regioselectively prepared by [3+3]-cyclization of 1,3-bis(trimethylsilyloxy)-7-chloro-hepta-1,3-dienes with 3-silyloxy-2-eno-1-ones and Subsequent intramolecular Williamson reactions of the salicylates thus formed. (C) 2004 Elsevier Ltd. All rights reserved.