(6aR,7aS,9aS)-9,9-dichloro-6a,9a-dimethyl-6,6a,7,7a,9,9a-hexahydro-4H-cyclobuta[a]phenalen-8(5H)-one | 1527483-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (6aR,7aS,9aS)-9,9-dichloro-6a,9a-dimethyl-6,6a,7,7a,9,9a-hexahydro-4H-cyclobuta[a]phenalen-8(5H)-one
• CAS: 1527483-05-1
• 化学式: C₁₇H₁₈Cl₂O
• 分子量: 309.235
• InChiKey: QPFAEKSMENAOQL-DAXOMENPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (6aR,7aS,9aS)-9,9-dichloro-6a,9a-dimethyl-6,6a,7,7a,9,9a-hexahydro-4H-cyclobuta[a]phenalen-8(5H)-one 在 sodium hypochlorite 、 rhodium(III) chloride hydrate 作用下， 以 四氯化碳 、 水 为溶剂， 以85%的产率得到(6aR,7aS,10aS)-6a,10a-dimethyl-6,6a,7,7a-tetrahydro-4H-phenaleno[1,2-c]furan-8,10(5H,10aH)-dione
  参考文献：
  名称：

  Useful Catalytic Enantioselective Cationic Double Annulation Reactions Initiated at an Internal π-Bond: Method and Applications

  摘要：

  The 1:1 complex of o,o'-dichloro-R-BINOL and SbCl5 initiates the enantioselective cationic polycyclization of polyunsaturated substrates at a predictable pi-bond which may be either terminal or, as shown herein, internal. The extension of this powerful construction to internal pi-bonds expands the scope of this method and opens up very short pathways to numerous chiral polycyclic molecules, including natural products and their analogues. Especially simple synthetic routes are disclosed that provide access to dysideapalaunic acid, dehydroabietic acid, and epipodocarpic acid and illustrate, the value of this enantioselective approach.

  DOI：

  10.1021/ja4125093
• 作为产物：
  描述：

  1-(4,4-dibromobut-3-en-1-yl)-1-methyl-1,2,3,4-tetrahydronaphthalene 在 正丁基锂 、 三氟甲磺酸 、 copper(I) bromide 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (6aR,7aS,9aS)-9,9-dichloro-6a,9a-dimethyl-6,6a,7,7a,9,9a-hexahydro-4H-cyclobuta[a]phenalen-8(5H)-one
  参考文献：
  名称：

  Useful Catalytic Enantioselective Cationic Double Annulation Reactions Initiated at an Internal π-Bond: Method and Applications

  摘要：

  The 1:1 complex of o,o'-dichloro-R-BINOL and SbCl5 initiates the enantioselective cationic polycyclization of polyunsaturated substrates at a predictable pi-bond which may be either terminal or, as shown herein, internal. The extension of this powerful construction to internal pi-bonds expands the scope of this method and opens up very short pathways to numerous chiral polycyclic molecules, including natural products and their analogues. Especially simple synthetic routes are disclosed that provide access to dysideapalaunic acid, dehydroabietic acid, and epipodocarpic acid and illustrate, the value of this enantioselective approach.

  DOI：

  10.1021/ja4125093