3-chloro-4-(trimethylsilyloxy)pent-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: 3-chloro-4-(trimethylsilyloxy)pent-3-en-2-one
• 英文别名: 3-Chloro-4-(trimethylsilyloxy)-3-penten-2-one；3-chloro-4-trimethylsilyloxypent-3-en-2-one
• 化学式: C₈H₁₅ClO₂Si
• 分子量: 206.744
• InChiKey: VHVPUEFKZDHTSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  3-chloro-4-(trimethylsilyloxy)pent-3-en-2-one 在 2,6-二甲基吡啶 、 正丁基锂 、 silica gel 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 5.75h， 生成 3-Chloro-2,4-dimethyl-5-methylene-4-trimethylsilanyloxy-cyclopent-2-enone
  参考文献：
  名称：

  Cyclopentannelation Reaction for Rapid Assembly of Multifunctional Products. (d,l)-Desepoxymethylenomycin a Methyl Ester

  摘要：

  The scope of the alkoxyallene cationic cyclopentannelation reaction has been examined. Non-hydrogen substituents at both C4 and C5 were required for synthetically useful yields. Whereas the cyclization appeared to be subject to steric constraints, it was relatively insensitive to electronic effects. An efficient synthesis of (d,l)- , desepoxymethylenomycin A methyl ester has been described.

  DOI：

  10.1080/00397919408011309

文献信息

• Synthesis of functionalized 2-(arylthio)benzoates by formal [3+3] cyclizations of 3-arylthio-1-silyloxy-1,3-butadienes with 3-silyloxy-2-en-1-ones and 1,3-diacylcyclopropanes
  作者：Inam Iqbal、Muhammad Imran、Nasir Rasool、Muhammad A. Rashid、Munawar Hussain、Alexander Villinger、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2009.06.119

  日期：2009.9

  Functionalized 2-(arylthio)benzoates are prepared by formal [3+3] cyclizations of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 3-silyloxy-2-en-1-ones and 1,1-diacylcyclopropanes.

  通过3-芳基硫基-1-三甲基甲硅烷氧基-1，3-丁二烯与3-甲硅烷氧基-2-烯-1-酮和1，1-二酰基环丙烷的正式[3 + 3]环化反应来制备官能化的2-（芳硫基）苯甲酸酯。
• Synthesis of Biaryls, Fluorenones, Cyclopenta[<i>def</i>]phenanthren-4-ones, and Benzophenones Based on Formal [3+3] Cyclocondensations of 1,3-Bis(silyloxy)buta-1,3-dienes with 3-(Silyloxy)-2-en-1-ones
  作者：Peter Langer、Stefanie Reim、Matthias Lau、Muhammad Adeel、Ibrar Hussain、Mirza Yawer、Abdolmajid Riahi、Zafar Ahmed、Christine Fischer、Helmut Reinke

  DOI：10.1055/s-0028-1083309

  日期：——

  prepared by cyclization of 3-aryl-3-(silyloxy­)-2-en-1-ones with 1,3-bis(silyloxy)buta-1,3-dienes and subsequent intramolecular Friedel-Crafts acylation of the 6-aryl­salicylates thus formed. In this context, the synthesis of novel cyclopenta[def]phenanthren-4-ones is reported. In addition, the synthesis of functionalized benzophenones is reported. cyclizations - fluorenones - regioselectivity - silyl

  分四个步骤有效地制备了官能化的芴酮。1,3-双（甲硅烷氧基）丁1,3-二烯与3-（甲硅烷氧基）-2-en-1-one的[3 + 3]环化提供了水杨酸酯，将其转化为烯醇三氟甲磺酸酯。后者与芳基硼酸的Suzuki交叉偶联反应得到2-（甲氧基羰基）联芳基，其随后通过分子内Friedel-Crafts酰化作用转化为目标分子。另外，通过将3-芳基-3-（甲硅烷氧基）-2-烯-1-酮与1,3-双（甲硅烷氧基）丁烯-1,3-二烯环合，随后进行分子内弗里德尔-克拉夫茨制备1-羟基芴酮这样形成的6-芳基水杨酸酯的酰化。在这种情况下，新型环戊四烯的合成[ def] phenanthren-4-ones被报道。另外，已经报道了官能化的二苯甲酮的合成。 环化-芴酮 -区域选择性-甲硅烷基烯醇醚
• Diversity-Oriented Synthesis of Chlorinated Arenes by One-Pot Cyclizations of 4-Chloro-1,3-bis(trimethylsilyloxy)buta-1,3-dienes
  作者：Verena Wolf、Muhammad Adeel、Stefanie Reim、Alexander Villinger、Christine Fischer、Peter Langer

  DOI：10.1002/ejoc.200900816

  日期：2009.11

  A variety of 3-chlorosalicylates were prepared by one-potcyclizations of the first reported 4-chloro-1,3-bis(trimethylsilyloxy)buta-1,3-dienes with various 1,3-dielectrophiles. These include cyclizations with 3-silyloxy-2-en-1-ones, 3-aryl-3-silyloxy-2-en-1-ones, 1-methoxy-1-en-3-ones, 1,1-bis(methylthio)-1-en-3-ones, 3-oxo orthoesters, 1,1,3,3-tetraethoxypropanes, 1,1-diacetylcyclopropane, and 3-formylchromones

  通过首次报道的 4-氯-1,3-双（三甲基甲硅烷氧基）丁-1,3-二烯与各种 1,3-亲电试剂的单锅环化反应制备了多种 3-氯水杨酸酯。这些包括与 3-甲硅烷氧基-2-烯-1-酮、3-芳基-3-甲硅烷氧基-2-烯-1-酮、1-甲氧基-1-烯-3-酮、1,1-双(甲硫基)-1-en-3-酮、3-氧代原酸酯、1,1,3,3-四乙氧基丙烷、1,1-二乙酰环丙烷和 3-甲酰基色酮。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Regioselective Synthesis of Functionalized Biaryls Based on the First [3+3] Cyclocondensations of 4-Aryl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes
  作者：Peter Langer、Muhammad Adeel、Muhammad Rashid、Nasir Rasool、Rasheed Ahmad、Alexander Villinger、Helmut Reinke、Christine Fischer

  DOI：10.1055/s-0028-1083298

  日期：2009.1

  Sterically encumbered biaryls were regioselectively prepared by formal [3+3] cyclocondensations of novel 4-aryl-1,3-bis(trimethylsilyloxy)-1,3-dienes. cyclizations - salicylates - biaryls - silyl enol ethers

  通过新颖的4-芳基-1,3-双（三甲基甲硅烷氧基）-1,3-二烯的形式[3 + 3]环缩合，选择性地制备立体受限的联芳基。 环化-水杨酸酯-联芳基-甲硅烷基烯醇醚
• Synthesis of functionalized 2-alkoxybenzoates, 2-aryloxybenzoates and xanthones based on formal [3+3] cyclocondensations of 3-alkoxy- and 3-aryloxy-1-silyloxy-1,3-butadienes with 3-silyloxy-2-en-1-ones
  作者：Gerson Mroß、Helmut Reinke、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2009.02.052

  日期：2009.5

  Functionalized 2-alkoxy- and 2-aryloxybenzoates were prepared by formal [3+3] cyclocondensations of 3-alkoxy- and 3-aryloxy-1-silyloxy-1,3-butadienes with 3-silyloxy-2-en-1-ones. The reaction of 2-aryloxybenzoates with concentrated sulfuric acid resulted in the formation of xanthones. (C) 2009 Elsevier Ltd. All rights reserved.