trans-4-phenyl-2-triethylsilyloxy-1,3-butadiene

• 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: trans-4-phenyl-2-triethylsilyloxy-1,3-butadiene
• 英文别名: (E)-triethyl((4-phenylbuta-1,3-dien-2-yl)oxy)silane；triethyl-[(3E)-4-phenylbuta-1,3-dien-2-yl]oxysilane
• 化学式: C₁₆H₂₄OSi
• 分子量: 260.451
• InChiKey: LGLRBKCTLNHTER-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  18
• 可旋转键数：
  7
• 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：

  trans-4-phenyl-2-triethylsilyloxy-1,3-butadiene 在 正丁基锂 、 1,1'-bis(di-tertbutylphosphino)ferrocene 、 palladium diacetate 、 三正丁基氟化锡 、 二异丙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 、 正己烷 、 甲苯 为溶剂， 反应 2.0h， 生成 (E)-3-phenyl-2-styryl-1H-indole
  参考文献：
  名称：

  钯通过双重α-芳基化策略催化合成2-烯基-3-芳基吲哚：降血脂药氟伐他汀的正式合成†

  摘要：

  已经开发了用于合成取代的2-烯基-3-芳基吲哚的新方法。该策略包括钯催化烯酮的TES-烯醇醚的双α-芳基化作为关键步骤。这种方法产生的产物具有非常高的产率，并且区域选择性是排他的。我们还在降胆固醇药物氟伐他汀的正式合成中成功使用了这种双重α-芳基化方法。

  DOI：

  10.1039/c5ob01632k
• 作为产物：
  描述：

  三乙基硅基三氟甲磺酸酯 、 苄叉丙酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以87%的产率得到trans-4-phenyl-2-triethylsilyloxy-1,3-butadiene
  参考文献：
  名称：

  Asymmetric syntheses of diarylheptanoid natural products (−)-centrolobine and (−)-de-O-methylcentrolobine via hetero-Diels–Alder reaction catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate]

  摘要：

  Catalytic asymmetric syntheses of (-)-centrolobine and (-)-de-O-methylcentrolobine have been achieved, incorporating a hetero-Diels-Alder (HDA) reaction between 4-aryl-2-silyloxy-1,3-butadienes and phenylpropargyl aldehyde derivatives as a key step. The HDA reaction using dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh-2(R-BPTPI)(4), as a chiral Lewis acid catalyst provides exclusively cis-2,6-disubstituted tetrahydropyran-4-ones in up to 93% ee. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.003

文献信息

• Total Synthesis of Resorcylic Acid Lactone (−)‐Neocosmosin A Using Palladium‐Catalyzed α‐Arylation of Enones as the Key Step
  作者：Govind Goroba Pawar、Ajit Prabhakar Kale、Pooja Sah、Manmohan Kapur

  DOI：10.1002/ejoc.202201277

  日期：2023.1.17

  The total synthesis of the 14-membered resorcylic acid lactone (−)-neocosmosin A is described. The key step in the synthesis is the palladium-catalyzed α-arylation of TES-enol ethers of enones. The employment of the α-arylation approach to this class of resorcylic acid lactones is a new approach, which has the scope of being generalized into a unified approach for the synthesis of this class of natural

  描述了 14 元间苯二甲酸内酯 (−)-neocosmosin A 的全合成。合成的关键步骤是钯催化的烯酮的 TES-烯醇醚的 α-芳基化。对此类间苯二甲酸内酯采用 α-芳基化方法是一种新方法，具有推广为此类天然产物合成的统一方法的范围。
• Palladium-Catalyzed α-Arylation of Enones in the Synthesis of 2-Alkenylindoles and Carbazoles
  作者：Ajit Prabhakar Kale、Gangam Srikanth Kumar、Arun Raj Kizhakkayil Mangadan、Manmohan Kapur

  DOI：10.1021/acs.orglett.5b00324

  日期：2015.3.6

  A new unified strategy has been developed for the synthesis of substituted 2-alkenylindoles and carbazoles. The strategy uses palladium-catalyzed alpha-arylation of TES-enol ethers of enones as the key step. The method is highly regioselective, provides good yields, and is expected to have wide application.
• Asymmetric syntheses of diarylheptanoid natural products (−)-centrolobine and (−)-de-O-methylcentrolobine via hetero-Diels–Alder reaction catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate]
  作者：Takuya Washio、Reika Yamaguchi、Takumi Abe、Hisanori Nambu、Masahiro Anada、Shunichi Hashimoto

  DOI：10.1016/j.tet.2007.09.003

  日期：2007.11

  Catalytic asymmetric syntheses of (-)-centrolobine and (-)-de-O-methylcentrolobine have been achieved, incorporating a hetero-Diels-Alder (HDA) reaction between 4-aryl-2-silyloxy-1,3-butadienes and phenylpropargyl aldehyde derivatives as a key step. The HDA reaction using dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh-2(R-BPTPI)(4), as a chiral Lewis acid catalyst provides exclusively cis-2,6-disubstituted tetrahydropyran-4-ones in up to 93% ee. (C) 2007 Elsevier Ltd. All rights reserved.
• Regioselectivity Switch Achieved in the Palladium Catalyzed α-Arylation of Enones by Employing the Modified Kuwajima–Urabe Conditions
  作者：Ajit Prabhakar Kale、Govind Goroba Pawar、Manmohan Kapur

  DOI：10.1021/ol300401c

  日期：2012.4.6

  A new regioselective approach to the synthesis of alpha-aryl enones is reported. This represents an important application of the Kuwajima-Urabe protocol toward the synthesis of this simple albeit complex functional array. Several a-aryl enones were synthesized by the palladium catalyzed arylation of triethylsilylenol ethers of enones with high regioselectivity and broad scope, utilizing sterically encumbered electron-rich phosphine ligands to drive the reaction.
• Palladium-catalyzed synthesis of 2-alkenyl-3-arylindoles via a dual α-arylation strategy: formal synthesis of the antilipemic drug fluvastatin
  作者：Ajit Prabhakar Kale、Gangam Srikanth Kumar、Manmohan Kapur

  DOI：10.1039/c5ob01632k

  日期：——

  approach has been developed for the synthesis of substituted 2-alkenyl-3-arylindoles. The strategy comprises palladium-catalyzed dual α-arylation of TES-enol ethers of enones as the key step. This methodology results in products with very good yields and the regioselectivity is exclusive. We have also successfully used this dual α-arylation methodology in the formal synthesis of the cholesterol-lowering drug

  已经开发了用于合成取代的2-烯基-3-芳基吲哚的新方法。该策略包括钯催化烯酮的TES-烯醇醚的双α-芳基化作为关键步骤。这种方法产生的产物具有非常高的产率，并且区域选择性是排他的。我们还在降胆固醇药物氟伐他汀的正式合成中成功使用了这种双重α-芳基化方法。