3,3,5,6,8,8-hexamethyl-1,2,3,8-tetrahydropyrano[3,2-f]chromene | 138641-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,3,5,6,8,8-hexamethyl-1,2,3,8-tetrahydropyrano[3,2-f]chromene
• 英文别名: 3,3,5,6,8,8-hexamethyl-9,10-dihydropyrano[3,2-f]chromene
• CAS: 138641-74-4
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: YIXBWSUDDGSIEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  72-74 °C
• 沸点：
  374.3±42.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,3,5,6,8,8-hexamethyl-1,2,3,8-tetrahydropyrano[3,2-f]chromene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 3,3,5,6,8,8-hexamethyl-3,8-dihydropyrano[3,2-f]chromene
  参考文献：
  名称：

  Novel tocopherol derivatives. Part 32: On the bromination of pyrano[3,2-f]chromenes related to γ-tocopherol

  摘要：

  While bromination of gamma-tocopherol (2) with elemental bromine affords 5-bromo-gamma-tocopherol quantitatively (3), the analogous reaction of its truncated model compound, 2,2,7,8-tetramethylchromanol (2a) is known to be accompanied by side reactions and to produce hitherto unknown byproducts. These compounds originate from pyrano[3,2-f]chromene (6), a byproduct in the synthesis of model compound 2a, which affords bromochromene 7 as the major product. The reaction mechanism was shown to proceed via chromene 8 and its 1,2-dibromo addition compound 9, which eliminates HBr in an E1 process to finally afford 7. Analytical data including crystal structures of both 6 and 7 are reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.070
• 作为产物：
  描述：

  2-甲基-3-丁烯-2-醇 在 甲酸 、 溴 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 3,3,5,6,8,8-hexamethyl-1,2,3,8-tetrahydropyrano[3,2-f]chromene
  参考文献：
  名称：

  Novel tocopherol derivatives. Part 32: On the bromination of pyrano[3,2-f]chromenes related to γ-tocopherol

  摘要：

  While bromination of gamma-tocopherol (2) with elemental bromine affords 5-bromo-gamma-tocopherol quantitatively (3), the analogous reaction of its truncated model compound, 2,2,7,8-tetramethylchromanol (2a) is known to be accompanied by side reactions and to produce hitherto unknown byproducts. These compounds originate from pyrano[3,2-f]chromene (6), a byproduct in the synthesis of model compound 2a, which affords bromochromene 7 as the major product. The reaction mechanism was shown to proceed via chromene 8 and its 1,2-dibromo addition compound 9, which eliminates HBr in an E1 process to finally afford 7. Analytical data including crystal structures of both 6 and 7 are reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.070