(2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydroisoquinoline | 393780-93-3

• 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: (2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 3,4-dihydro-1H-isoquinolin-2-yl-[(1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-6-yl]methanone
• CAS: 393780-93-3
• 化学式: C₂₁H₂₇NO₆
• 分子量: 389.448
• InChiKey: SXLJPAVRMCJXMR-GRXQJBFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydroisoquinoline 在 氢氧化钾 、 叔丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 98.25h， 生成 (R)-(+)-1-甲基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  Diastereoselective Alkylation of 2,3,4,6-Di-O-isopropylidene-2-keto-l-gulonic Amides. Application to the Asymmetric Synthesis of 1-Substituted-1,2,3,4-tetrahydroisoquinolines and 1-Substituted-1,2,3,4,-tetrahydro-β-carbolines

  摘要：

  The diastereoselective alkylation of amides 3a,b and 7a,b derived from gulonic acid is described. Substituted compounds are obtained in good yield and high diastereoselectivity. A mechanistic investigation establishes that the diastereoselectivity did not arise from an initial asymmetric deprotonation. The stereochemistry is then determined during the alkylation step.

  DOI：

  10.1021/jo0155658
• 作为产物：
  描述：

  四氢异喹啉 、 调呋酸 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到(2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Diastereoselective Alkylation of 2,3,4,6-Di-O-isopropylidene-2-keto-l-gulonic Amides. Application to the Asymmetric Synthesis of 1-Substituted-1,2,3,4-tetrahydroisoquinolines and 1-Substituted-1,2,3,4,-tetrahydro-β-carbolines

  摘要：

  The diastereoselective alkylation of amides 3a,b and 7a,b derived from gulonic acid is described. Substituted compounds are obtained in good yield and high diastereoselectivity. A mechanistic investigation establishes that the diastereoselectivity did not arise from an initial asymmetric deprotonation. The stereochemistry is then determined during the alkylation step.

  DOI：

  10.1021/jo0155658

文献信息

• Diastereoselective Alkylation of 2,3,4,6-Di-<i>O</i>-isopropylidene-2-keto-<scp>l</scp>-gulonic Amides. Application to the Asymmetric Synthesis of 1-Substituted-1,2,3,4-tetrahydroisoquinolines and 1-Substituted-1,2,3,4,-tetrahydro-β-carbolines
  作者：Stéphane Adam、Xavier Pannecoucke、Jean-Claude Combret、Jean-Charles Quirion

  DOI：10.1021/jo0155658

  日期：2001.12.1

  The diastereoselective alkylation of amides 3a,b and 7a,b derived from gulonic acid is described. Substituted compounds are obtained in good yield and high diastereoselectivity. A mechanistic investigation establishes that the diastereoselectivity did not arise from an initial asymmetric deprotonation. The stereochemistry is then determined during the alkylation step.