(4RS,5RS)-6-benzyloxy-5-hydroxy-4-(2-nitroethoxy)-hex-2-enoic acid ethyl ester

• 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: (4RS,5RS)-6-benzyloxy-5-hydroxy-4-(2-nitroethoxy)-hex-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4R,5R)-5-hydroxy-4-(2-nitroethoxy)-6-phenylmethoxyhex-2-enoate
• 化学式: C₁₇H₂₃NO₇
• 分子量: 353.372
• InChiKey: CJQAWXOFAYYMHB-GUFYHEMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4RS,5RS)-6-benzyloxy-5-hydroxy-4-(2-nitroethoxy)-hex-2-enoic acid ethyl ester 、 甲基磺酰氯 在 吡啶 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Stereospecific interconversion of cis- and trans-γ,δ-epoxy α,β-unsaturated ester systems

  摘要：

  The unprecedented, stereospecific interconversion of cis- and trans-gamma,delta-epoxy alpha,beta-unsaturated ester systems has been realized, which involves the palladium-catalyzed stereospecific alkoxy or hydroxy substitution reaction with double inversion of configuration at the gamma-position as the key step. The new methodology is not only applicable to various disubstituted and trisubstituted epoxy unsaturated esters, but also these interconversions proceed with an extremely high degree of stereoselectivity and efficiency. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.084
• 作为产物：
  描述：

  2-硝基乙醇 、 ethyl 6-benzyloxy-trans-4,5-epoxy-(E)-2-hexenoate 在 boron trioxide 、 四(三苯基膦)钯 、 频哪醇 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(4RS,5RS)-6-benzyloxy-5-hydroxy-4-(2-nitroethoxy)-hex-2-enoic acid ethyl ester
  参考文献：
  名称：

  Stereospecific interconversion of cis- and trans-γ,δ-epoxy α,β-unsaturated ester systems

  摘要：

  The unprecedented, stereospecific interconversion of cis- and trans-gamma,delta-epoxy alpha,beta-unsaturated ester systems has been realized, which involves the palladium-catalyzed stereospecific alkoxy or hydroxy substitution reaction with double inversion of configuration at the gamma-position as the key step. The new methodology is not only applicable to various disubstituted and trisubstituted epoxy unsaturated esters, but also these interconversions proceed with an extremely high degree of stereoselectivity and efficiency. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.084

文献信息

• Palladium-Catalyzed Stereospecific Substitution of α,β-Unsaturated γ,δ-Epoxy Esters by Alcohols with Double Inversion of Configuration: Synthesis of 4-Alkoxy-5-hydroxy-2-pentenoates
  作者：Xiao-Qiang Yu、Fumihiko Yoshimura、Fumito Ito、Minoru Sasaki、Atsushi Hirai、Keiji Tanino、Masaaki Miyashita

  DOI：10.1002/anie.200703889

  日期：2008.1.11
• Stereospecific interconversion of cis- and trans-γ,δ-epoxy α,β-unsaturated ester systems
  作者：Xiao-Qiang Yu、Fumihiko Yoshimura、Keiji Tanino、Masaaki Miyashita

  DOI：10.1016/j.tetlet.2008.10.084

  日期：2008.12

  The unprecedented, stereospecific interconversion of cis- and trans-gamma,delta-epoxy alpha,beta-unsaturated ester systems has been realized, which involves the palladium-catalyzed stereospecific alkoxy or hydroxy substitution reaction with double inversion of configuration at the gamma-position as the key step. The new methodology is not only applicable to various disubstituted and trisubstituted epoxy unsaturated esters, but also these interconversions proceed with an extremely high degree of stereoselectivity and efficiency. (C) 2008 Elsevier Ltd. All rights reserved.