(R)-1-{(4S,5S)-5-[(E)-3-{[(allyloxy)carbonyl]oxy}-2-methylbuta-1,3-dien-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-3-methylbut-3-en-2-yl benzoate | 1429033-80-6

• 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: (R)-1-{(4S,5S)-5-[(E)-3-{[(allyloxy)carbonyl]oxy}-2-methylbuta-1,3-dien-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-3-methylbut-3-en-2-yl benzoate
• CAS: 1429033-80-6
• 化学式: C₂₆H₃₂O₇
• 分子量: 456.536
• InChiKey: JBCVKUKMVDWORD-UPWUXJIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-1-{(4S,5S)-5-[(E)-3-{[(allyloxy)carbonyl]oxy}-2-methylbuta-1,3-dien-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-3-methylbut-3-en-2-yl benzoate 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 邻二氯苯 为溶剂， 反应 24.0h， 以52%的产率得到(3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl benzoate
  参考文献：
  名称：

  A Stereoconvergent Intramolecular Diels–Alder Cycloaddition Related to the Construction of the Decalin Core of neo-Clerodane Diterpenoids

  摘要：

  Several examples of a highly specific, stereoconvergent intramolecular Diels-Alder cycloaddition that led to the trans-decalin core of neo-clerodane diterpenoids are described. The relative configuration adjacent to the dienophile, which led to C4 of the decalin system, as well as the electron withdrawing effects of various substituents and conformational rigidity of the Diels-Alder precursors were explored.

  DOI：

  10.1021/jo400029u
• 作为产物：
  描述：

  (R)-1-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-yl benzoate 在 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 mineral oil 为溶剂， 反应 19.08h， 生成 (R)-1-{(4S,5S)-5-[(E)-3-{[(allyloxy)carbonyl]oxy}-2-methylbuta-1,3-dien-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-3-methylbut-3-en-2-yl benzoate
  参考文献：
  名称：

  A Stereoconvergent Intramolecular Diels–Alder Cycloaddition Related to the Construction of the Decalin Core of neo-Clerodane Diterpenoids

  摘要：

  Several examples of a highly specific, stereoconvergent intramolecular Diels-Alder cycloaddition that led to the trans-decalin core of neo-clerodane diterpenoids are described. The relative configuration adjacent to the dienophile, which led to C4 of the decalin system, as well as the electron withdrawing effects of various substituents and conformational rigidity of the Diels-Alder precursors were explored.

  DOI：

  10.1021/jo400029u