trans-4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene | 960399-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: trans-4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene
• 英文别名: triethyl-[(3E)-4-(4-phenylmethoxyphenyl)buta-1,3-dien-2-yl]oxysilane
• CAS: 960399-11-5
• 化学式: C₂₃H₃₀O₂Si
• 分子量: 366.576
• InChiKey: NIHBKKPJPUTNBL-BUHFOSPRSA-N

物化性质

• 沸点：
  458.0±33.0 °C(predicted)
• 密度：
  0.997±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-methanesulfonyloxyphenyl)propynal 、 trans-4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene 在 rhodium(II) chiral 2-piperidinone-based complex 四丁基氟化铵 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 12.5h， 以290 mg的产率得到(2R,6S)-2-(4-methanesulfonyloxyphenylethynyl)-6-(4-benzyloxyphenyl)tetrahydropyran-4-one
  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
• 作为产物：
  描述：

  1-(4-苄氧基苯基)丁-1-烯-3-酮 、 三乙基硅基三氟甲磺酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到trans-4-(4-benzyloxyphenyl)-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

• Catalytic asymmetric hetero-Diels–Alder route to a key intermediate for the synthesis of calyxin L
  作者：Takuya Washio、Hisanori Nambu、Masahiro Anada、Shunichi Hashimoto

  DOI：10.1016/j.tetasy.2007.10.025

  日期：2007.10

  A catalytic asymmetric formal synthesis of diarylheptanoid natural product calyxin L has been achieved by incorporating an enantio- and diastereoselective hetero-Diels-Alder (HDA) reaction, a Suzuki-Miyaura coupling, and a stereocontrolled catalytic hydrogenation of 2,4,6-trisubstituted dihydropyran as the key steps. The HDA reaction between 4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene and (4-benzenesulfonyloxyphenyl)propynal catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh-2(R-BPTPI)(4), provided cis-2,6-disubstituted tetrahydropyran-4-one in 91% yield with 91% ee. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.