(Z)-5-(2-(tert-butyldimethylsilyloxy)phenyl)-1-deuterio-pent-2-enal | 1360054-47-2

• 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: (Z)-5-(2-(tert-butyldimethylsilyloxy)phenyl)-1-deuterio-pent-2-enal
• 英文别名: (Z)-5-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]-1-deuteriopent-2-en-1-one
• CAS: 1360054-47-2
• 化学式: C₁₇H₂₆O₂Si
• 分子量: 291.47
• InChiKey: OXMPVRDUURCYLB-JQNGMUKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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)-5-(2-(tert-butyldimethylsilyloxy)phenyl)-1-deuterio-pent-2-enal 在 吡啶 、 titanium(IV) isopropylate 、 四丁基氟化铵 、 三正丁基氢锡 、 (R)-1,1'-Bi-2-naphthol 、 silica gel 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 52.5h， 生成 (S,E)-1-deuterio-5-(2-hydroxyphenyl)pent-2-enyl 2,2,2-trichloroacetimidate
  参考文献：
  名称：

  Palladium(II)-Catalyzed Enantioselective Synthesis of 2-Vinyl Oxygen Heterocycles

  摘要：

  2-Vinylchromanes (1), 2-vinyl-1,4-benzodioxanes (2), and 2,3-dihydro-2-vinyl-2H-1,4-benzoxazines (3) can be prepared in high yields (90-98%) and excellent enantiomeric purities (87-98% ee) by [COP-OAc](2)-catalyzed cyclization of phenolic (E)-allylic trichloroacetimidate precursors. Deuterium-labeling and computational experiments are consistent with these cyclization reactions taking place by an anti-oxypalladation/syn-deoxypalladation mechanism. 2-Vinylchromanes can also be prepared in good yields and high enantiomeric purities from analogous (E)-allylic acetate precursors, which constitutes the first report that acetate is a competent leaving group in COP-catalyzed enantioselective S(N)2' substitution reactions.

  DOI：

  10.1021/jo202553a
• 作为产物：
  描述：

  2-(4,4-dibromo-but-3-enyl)phenol 在 咪唑 、 sodium tetrahydroborate 、 正丁基锂 、 lithium aluminium deuteride 、 乙醇 、 sulfur trioxide pyridine complex 、 氢气 、 nickel(II) acetate tetrahydrate 、 乙二胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.83h， 生成 (Z)-5-(2-(tert-butyldimethylsilyloxy)phenyl)-1-deuterio-pent-2-enal
  参考文献：
  名称：

  Palladium(II)-Catalyzed Enantioselective Synthesis of 2-Vinyl Oxygen Heterocycles

  摘要：

  2-Vinylchromanes (1), 2-vinyl-1,4-benzodioxanes (2), and 2,3-dihydro-2-vinyl-2H-1,4-benzoxazines (3) can be prepared in high yields (90-98%) and excellent enantiomeric purities (87-98% ee) by [COP-OAc](2)-catalyzed cyclization of phenolic (E)-allylic trichloroacetimidate precursors. Deuterium-labeling and computational experiments are consistent with these cyclization reactions taking place by an anti-oxypalladation/syn-deoxypalladation mechanism. 2-Vinylchromanes can also be prepared in good yields and high enantiomeric purities from analogous (E)-allylic acetate precursors, which constitutes the first report that acetate is a competent leaving group in COP-catalyzed enantioselective S(N)2' substitution reactions.

  DOI：

  10.1021/jo202553a

文献信息

• Palladium(II)-Catalyzed Enantioselective Synthesis of 2-Vinyl Oxygen Heterocycles
  作者：Jeffrey S. Cannon、Angela C. Olson、Larry E. Overman、Nicole S. Solomon

  DOI：10.1021/jo202553a

  日期：2012.2.17

  2-Vinylchromanes (1), 2-vinyl-1,4-benzodioxanes (2), and 2,3-dihydro-2-vinyl-2H-1,4-benzoxazines (3) can be prepared in high yields (90-98%) and excellent enantiomeric purities (87-98% ee) by [COP-OAc](2)-catalyzed cyclization of phenolic (E)-allylic trichloroacetimidate precursors. Deuterium-labeling and computational experiments are consistent with these cyclization reactions taking place by an anti-oxypalladation/syn-deoxypalladation mechanism. 2-Vinylchromanes can also be prepared in good yields and high enantiomeric purities from analogous (E)-allylic acetate precursors, which constitutes the first report that acetate is a competent leaving group in COP-catalyzed enantioselective S(N)2' substitution reactions.