(5S,9S,14S)-18,20-dimethoxy-7,7,14-trimethyl-6,8,15-trioxatricyclo[15.4.0.05,9]henicosa-1(17),18,20-trien-11-yne-10,16-dione | 1269765-84-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (5S,9S,14S)-18,20-dimethoxy-7,7,14-trimethyl-6,8,15-trioxatricyclo[15.4.0.05,9]henicosa-1(17),18,20-trien-11-yne-10,16-dione
• CAS: 1269765-84-5
• 化学式: C₂₃H₂₈O₇
• 分子量: 416.471
• InChiKey: ZVBKJIHYWGMOOB-DHUIEDIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S,9S,14S)-18,20-dimethoxy-7,7,14-trimethyl-6,8,15-trioxatricyclo[15.4.0.05,9]henicosa-1(17),18,20-trien-11-yne-10,16-dione 在 吡啶 、 氢气 作用下， 以 甲苯 为溶剂， 18.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以80%的产率得到
  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：

  2,4-dimethoxy-6-[3-[(4S,5S)-5-[methoxy(methyl)carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propyl]benzoic acid 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.25h， 生成 (5S,9S,14S)-18,20-dimethoxy-7,7,14-trimethyl-6,8,15-trioxatricyclo[15.4.0.05,9]henicosa-1(17),18,20-trien-11-yne-10,16-dione
  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.