-α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-1,3-dioxolo<4,5-g>isoquinoline-5-methanol | 131079-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-1,3-dioxolo<4,5-g>isoquinoline-5-methanol
• 英文别名: 1,3-benzodioxol-5-yl(5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanol
• CAS: 131079-59-9；131079-60-2；131079-61-3；131079-62-4
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: AQIIKVSJKPVIPE-UHFFFAOYSA-N

物化性质

• 熔点：
  153.5-155.0 °C
• 沸点：
  517.6±50.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.18
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-6-<4,5-dihydro-4-(1-methylethyl)-2-oxazolyl>-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以90%的产率得到-α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-1,3-dioxolo<4,5-g>isoquinoline-5-methanol
  参考文献：
  名称：

  Synthesis of the phthalide isoquinoline alkaloids (-)-egenine, (-)-corytensine, and (-)-bicuculline by asymmetric carbonyl addition of chiral dipole-stabilized organometallics

  摘要：

  The asymmetric addition of metalated [(methylenedioxy)isoquinolyl]oxazolines is 100% selective for the erythro (alpha-hydroxybenzyl)isoquinoline diastereomers, with 2:1 selectivity of the two possible erythro stereoisomers. Enrichment to 100% ee after removal of the auxiliary and conversion to (-)-bicuculline and (+)-bicuculline diol establish the absolute configuration of the major addition product. Inversion of the C-9 hydroxyl affords entry into the threo series as well. The asymmetric carbonyl addition was used to synthesize, for the first time, the phthalide-isoquinoline hemiacetals corytensine and egenine, confirming the previously assigned structures and absolute configurations, and establishing the identity of egenine with decumbensine and of corytensine with epi-alpha-decumbensine.

  DOI：

  10.1021/jo00004a041