1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone | 1426679-88-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone
• 英文别名: 1-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-[(2S,6R)-6-(4-methoxyphenyl)oxan-2-yl]ethanone
• CAS: 1426679-88-0
• 化学式: C₂₆H₃₆O₄Si
• 分子量: 440.655
• InChiKey: GAWCSRYNZYJJCL-UKILVPOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone 在 甲醇 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以75%的产率得到(+)-centrolobine
  参考文献：
  名称：

  A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps

  摘要：

  An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodivergent access to every representative member of the family. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.005
• 作为产物：
  描述：

  乙基5-(4-甲氧基苯基)-5-氧代戊酸酯 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 Noyori's catalyst 、 甲酸 、 potassium tert-butylate 、 四丁基氟化铵 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 68.5h， 生成 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2R,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone 、 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone
  参考文献：
  名称：

  A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps

  摘要：

  An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodivergent access to every representative member of the family. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.005

文献信息

• A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps
  作者：Gullapalli Kumaraswamy、Dasa Rambabu

  DOI：10.1016/j.tetasy.2013.01.005

  日期：2013.2

  An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodivergent access to every representative member of the family. (C) 2013 Elsevier Ltd. All rights reserved.