(1S)-trans-1,5,6,10b-tetrahydro-1-(1,3-benzodioxol-5-yl)-3H-oxazolo<4,3-a>1,3-dioxolo<4,5-g>isoquinolin-3-one | 131589-16-7

• 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: (1S)-trans-1,5,6,10b-tetrahydro-1-(1,3-benzodioxol-5-yl)-3H-oxazolo<4,3-a>1,3-dioxolo<4,5-g>isoquinolin-3-one
• 英文别名: (2R,3R)-3-(1,3-benzodioxol-5-yl)-4,12,14-trioxa-6-azatetracyclo[7.7.0.02,6.011,15]hexadeca-1(16),9,11(15)-trien-5-one
• CAS: 131589-16-7；131681-60-2
• 化学式: C₁₉H₁₅NO₆
• 分子量: 353.331
• InChiKey: UYZDPUHWCMJERO-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S)-trans-1,5,6,10b-tetrahydro-1-(1,3-benzodioxol-5-yl)-3H-oxazolo<4,3-a>1,3-dioxolo<4,5-g>isoquinolin-3-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以86%的产率得到-α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-6-methyl-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
• 作为产物：
  描述：

  -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 生成 (1S)-trans-1,5,6,10b-tetrahydro-1-(1,3-benzodioxol-5-yl)-3H-oxazolo<4,3-a>1,3-dioxolo<4,5-g>isoquinolin-3-one
  参考文献：
  名称：

  REIN, KATHLEEN S.;GAWLEY, ROBERT E., J. ORG. CHEM., 56,(1991) N, C. 1564-1569

  摘要：

  DOI：

文献信息

• REIN, KATHLEEN S.;GAWLEY, ROBERT E., J. ORG. CHEM., 56,(1991) N, C. 1564-1569
  作者：REIN, KATHLEEN S.、GAWLEY, ROBERT E.

  DOI：——

  日期：——
• Synthesis of the phthalide isoquinoline alkaloids (-)-egenine, (-)-corytensine, and (-)-bicuculline by asymmetric carbonyl addition of chiral dipole-stabilized organometallics
  作者：Kathleen S. Rein、Robert E. Gawley

  DOI：10.1021/jo00004a041

  日期：1991.2

  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.