(4R)-4-<(p-Nitrobenzoyl)oxy>-4-phenyl-1-butene | 154657-45-1

• 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: (4R)-4-<(p-Nitrobenzoyl)oxy>-4-phenyl-1-butene
• 英文别名: [(1R)-1-phenylbut-3-enyl] 4-nitrobenzoate
• CAS: 154657-45-1
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: SJPOKAGVCDYICK-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-4-<(p-Nitrobenzoyl)oxy>-4-phenyl-1-butene 在 chromium(VI) oxide 、 sodium hydroxide 、 thexylborane 作用下， 以 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 (R)-4-苯基丁内酯
  参考文献：
  名称：

  Chiral Synthesis via Organoboranes. 39. A Facile Synthesis of .gamma.-Substituted-.gamma.-butyrolactones in Exceptionally High Enantiomeric Purity

  摘要：

  Optically active homoallylic alcohols of exceptionally high enantiomeric purity (98-greater than or equal to 99 % ee) readily available via asymmetric allylboration were converted into p-nitrobenzoate esters and subjected to hydroboration followed by oxidation with CrO3 in aqueous acetic acid (10% H2O) to obtain the corresponding carboxylic acids with the same number of carbon atoms. The protecting ester group was hydrolyzed and the product lactonized in situ to the gamma-substituted gamma-butyrolactones 5 (R = Me, Pr, i-Pr, t-Bu, Ph, (E)-CH=CHCH3) usually without racemization and in good yields. The method is convenient and potentially valuable for. the synthesis of highly functionalized gamma-butyrolactones in high optical purity.

  DOI：

  10.1021/jo00081a014
• 作为产物：
  描述：

  (R)-1-Phenylbut-3-en-1-ol 、 4-硝基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到(4R)-4-<(p-Nitrobenzoyl)oxy>-4-phenyl-1-butene
  参考文献：
  名称：

  Chiral Synthesis via Organoboranes. 39. A Facile Synthesis of .gamma.-Substituted-.gamma.-butyrolactones in Exceptionally High Enantiomeric Purity

  摘要：

  Optically active homoallylic alcohols of exceptionally high enantiomeric purity (98-greater than or equal to 99 % ee) readily available via asymmetric allylboration were converted into p-nitrobenzoate esters and subjected to hydroboration followed by oxidation with CrO3 in aqueous acetic acid (10% H2O) to obtain the corresponding carboxylic acids with the same number of carbon atoms. The protecting ester group was hydrolyzed and the product lactonized in situ to the gamma-substituted gamma-butyrolactones 5 (R = Me, Pr, i-Pr, t-Bu, Ph, (E)-CH=CHCH3) usually without racemization and in good yields. The method is convenient and potentially valuable for. the synthesis of highly functionalized gamma-butyrolactones in high optical purity.

  DOI：

  10.1021/jo00081a014

文献信息

• Chiral Synthesis via Organoboranes. 39. A Facile Synthesis of .gamma.-Substituted-.gamma.-butyrolactones in Exceptionally High Enantiomeric Purity
  作者：Herbert C. Brown、Shekhar V. Kulkarni、Uday S. Racherla

  DOI：10.1021/jo00081a014

  日期：1994.1

  Optically active homoallylic alcohols of exceptionally high enantiomeric purity (98-greater than or equal to 99 % ee) readily available via asymmetric allylboration were converted into p-nitrobenzoate esters and subjected to hydroboration followed by oxidation with CrO3 in aqueous acetic acid (10% H2O) to obtain the corresponding carboxylic acids with the same number of carbon atoms. The protecting ester group was hydrolyzed and the product lactonized in situ to the gamma-substituted gamma-butyrolactones 5 (R = Me, Pr, i-Pr, t-Bu, Ph, (E)-CH=CHCH3) usually without racemization and in good yields. The method is convenient and potentially valuable for. the synthesis of highly functionalized gamma-butyrolactones in high optical purity.