(S)-5,6,7,8-tetrahydro-6-<4,5-dihydro-4-(1-methylethyl)-2-oxazolyl>-1,3-dioxolo<4,5-g>isoquinoline | 131589-12-3

• 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: (S)-5,6,7,8-tetrahydro-6-<4,5-dihydro-4-(1-methylethyl)-2-oxazolyl>-1,3-dioxolo<4,5-g>isoquinoline
• 英文别名: 6-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline
• CAS: 131589-12-3
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: HLCSSSNUQXGHCD-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5,6,7,8-tetrahydro-6-<4,5-dihydro-4-(1-methylethyl)-2-oxazolyl>-1,3-dioxolo<4,5-g>isoquinoline 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (-)-egenine
  参考文献：
  名称：

  Synthesis of (−)-egenine (decumbensine) by asymmetric carbonyl addition

  摘要：

  DOI：

  10.1016/s0040-4039(00)97451-3
• 作为产物：
  描述：

  5,6,7,8-四氢-[1,3]二氧并[4,5-g]异喹啉 、 (S)-2-ethoxy-4,5-dihydro-4-(1-methylethyl)oxazole 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 6.0h， 以78%的产率得到(S)-5,6,7,8-tetrahydro-6-<4,5-dihydro-4-(1-methylethyl)-2-oxazolyl>-1,3-dioxolo<4,5-g>isoquinoline
  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

文献信息

• REIN, KATHLEEN S.;GAWLEY, ROBERT E., TETRAHEDRON LETT., 31,(1990) N6, C. 3711-3714
  作者：REIN, KATHLEEN S.、GAWLEY, ROBERT E.

  DOI：——

  日期：——
• 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：——