5-((tert-butyldimethylsilyl)oxy)-5-(4-methoxyphenyl)pentanal | 1426679-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-((tert-butyldimethylsilyl)oxy)-5-(4-methoxyphenyl)pentanal
• 英文别名: (5R)-5-[tert-butyl(dimethyl)silyl]oxy-5-(4-methoxyphenyl)pentanal
• CAS: 1426679-86-8
• 化学式: C₁₈H₃₀O₃Si
• 分子量: 322.52
• InChiKey: UCJFUWGOXOQLGW-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-((tert-butyldimethylsilyl)oxy)-5-(4-methoxyphenyl)pentanal 在 potassium tert-butylate 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (R)-1-(4-methoxyphenyl)hex-5-en-1-ol
  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 、 4-二甲氨基吡啶 、 Noyori's catalyst 、 甲酸 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.5h， 生成 5-((tert-butyldimethylsilyl)oxy)-5-(4-methoxyphenyl)pentanal
  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

• Ru-catalyzed asymmetric hydrogenation of δ-keto Weinreb amides: enantioselective synthesis of (+)-Centrolobine
  作者：Mengmeng Zhao、Bin Lu、Guangni Ding、Kai Ren、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1039/c5ob02622a

  日期：——

  An efficient asymmetric hydrogenation of δ-keto Weinreb amides catalyzed by a Ru-Xyl-SunPhos-Daipen bifunctional catalyst has been achieved. This method afforded a series of enantio-enriched δ-hydroxy Weinreb amides in good yields (up to 93%) and enantioselectivities (up to 99%). This protocol was successfully applied to the synthesis of the key intermediate of (+)-Centrolobine.

  Ru-Xyl-SunPhos-Daipen双功能催化剂催化了δ-酮Weinreb酰胺的高效不对称加氢反应。该方法以良好的收率（最高93％）和对映选择性（最高99％）提供了一系列对映体富集的δ-羟基Weinreb酰胺。该方案已成功应用于（+）-Centrolobine关键中间体的合成。