[(2S)-pent-4-yn-2-yl] 2,4-dimethoxy-6-[3-[(4S,5S)-5-[methoxy(methyl)carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propyl]benzoate | 1269765-83-4

• 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: [(2S)-pent-4-yn-2-yl] 2,4-dimethoxy-6-[3-[(4S,5S)-5-[methoxy(methyl)carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propyl]benzoate
• CAS: 1269765-83-4
• 化学式: C₂₅H₃₅NO₈
• 分子量: 477.555
• InChiKey: CUOXVCSESDJEGD-BPXKWBHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S)-pent-4-yn-2-yl] 2,4-dimethoxy-6-[3-[(4S,5S)-5-[methoxy(methyl)carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propyl]benzoate 在 吡啶 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， -35.0~18.0 ℃ 、101.33 kPa 条件下， 反应 2.25h， 生成
  参考文献：
  名称：

  An Enantioselective Synthesis of the Resorcylic Acid Lactone L-783,277 via Addition of an Acetylide Anion to a Tethered Weinreb Amide

  摘要：

  Treatment of the terminal acetylene 12, readily obtained from the previously reported acid 10, with LiHMDS resulted in a novel macrocyclization reaction to give the cycloalkyne 13. Subjection of compound 13 to hydrogenation under Lindlar-type conditions afforded the Z-configured enone 14 that could be converted into the resorcylic acid lactone 4 upon treatment with BCl3 in CH2Cl2 at -78 degrees C.

  DOI：

  10.3987/com-10-s(e)67
• 作为产物：
  描述：

  在 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 氢气 、 三苯基膦 作用下， 以 甲苯 为溶剂， 18.0 ℃ 、344.75 kPa 条件下， 反应 52.0h， 生成 [(2S)-pent-4-yn-2-yl] 2,4-dimethoxy-6-[3-[(4S,5S)-5-[methoxy(methyl)carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propyl]benzoate
  参考文献：
  名称：

  An Enantioselective Synthesis of the Resorcylic Acid Lactone L-783,277 via Addition of an Acetylide Anion to a Tethered Weinreb Amide

  摘要：

  Treatment of the terminal acetylene 12, readily obtained from the previously reported acid 10, with LiHMDS resulted in a novel macrocyclization reaction to give the cycloalkyne 13. Subjection of compound 13 to hydrogenation under Lindlar-type conditions afforded the Z-configured enone 14 that could be converted into the resorcylic acid lactone 4 upon treatment with BCl3 in CH2Cl2 at -78 degrees C.

  DOI：

  10.3987/com-10-s(e)67

文献信息

• An Enantioselective Synthesis of the Resorcylic Acid Lactone L-783,277 via Addition of an Acetylide Anion to a Tethered Weinreb Amide
  作者：Martin G. Banwell、Andrew Lin、Anthony C. Willis

  DOI：10.3987/com-10-s(e)67

  日期：——

  Treatment of the terminal acetylene 12, readily obtained from the previously reported acid 10, with LiHMDS resulted in a novel macrocyclization reaction to give the cycloalkyne 13. Subjection of compound 13 to hydrogenation under Lindlar-type conditions afforded the Z-configured enone 14 that could be converted into the resorcylic acid lactone 4 upon treatment with BCl3 in CH2Cl2 at -78 degrees C.