(S,2E,4Z)-allyl 6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-hydroxy-2-methylhexa-2,4-dienoate | 1613221-32-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S,2E,4Z)-allyl 6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-hydroxy-2-methylhexa-2,4-dienoate
• CAS: 1613221-32-1
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: OZFVXXAJLPHJEI-XIBYAJADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S,2E,4Z)-allyl 6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-hydroxy-2-methylhexa-2,4-dienoate 、 trimethoxonium tetrafluoroborate 在 1,8-双二甲氨基萘 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(S,2E,4Z)-allyl 6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2-methylhexa-2,4-dienoate
  参考文献：
  名称：

  Total Synthesis of Herbimycin A

  摘要：

  Benzoquinone ansamycin antibiotic herbimycin A was synthesized in 19 linear steps and 4.2% yield. Highlighted is the design of a chiral γ-lactone as the C11-C15 synthon that enabled a facile catalytic asymmetric synthesis of the challenging C8-C20 fragment of the target molecule. The easy access to the stereogenic centers and high overall yield made the strategy applicable in the molecular editing of benzoquinone ansamycins.

  DOI：

  10.1021/ol5012899
• 作为产物：
  描述：

  (2E,4Z,6S,7R)-allyl 6,7,8-trihydroxy-2-methylocta-2,4-dienoate 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以71%的产率得到(S,2E,4Z)-allyl 6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-hydroxy-2-methylhexa-2,4-dienoate
  参考文献：
  名称：

  Total Synthesis of Herbimycin A

  摘要：

  Benzoquinone ansamycin antibiotic herbimycin A was synthesized in 19 linear steps and 4.2% yield. Highlighted is the design of a chiral γ-lactone as the C11-C15 synthon that enabled a facile catalytic asymmetric synthesis of the challenging C8-C20 fragment of the target molecule. The easy access to the stereogenic centers and high overall yield made the strategy applicable in the molecular editing of benzoquinone ansamycins.

  DOI：

  10.1021/ol5012899