(2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydro-9-ethoxymethyl-pyrido[3,4]indole | 393781-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 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-tetrahydro-9-ethoxymethyl-pyrido[3,4]indole
• 英文别名: [9-(ethoxymethyl)-3,4-dihydro-1H-pyrido[3,4-b]indol-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: 393781-05-0
• 化学式: C₂₆H₃₄N₂O₇
• 分子量: 486.565
• InChiKey: DJWFKJIMQNIVHY-IMIIHFCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  80.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙基溴苯 、 (2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydro-9-ethoxymethyl-pyrido[3,4]indole 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 1-phenethyl-2-(2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydro-9-ethoxymethyl-pyrido[3,4]indole 、 1-phenethyl-2-(2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydro-9-ethoxymethyl-pyrido[3,4]indole
  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：

  1,2,3,4-四氢-9H-吡啶[3,4-B]并吲哚 在 N-甲基吗啉 、 四甲基乙二胺 、 potassium hydride 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2',2',5',5'-tetramethyl-tetrahydro-1',3',4',6',8'-pentaxocyclopenta[a]indene-8'a-carbonyl)-1,2,3,4-tetrahydro-9-ethoxymethyl-pyrido[3,4]indole
  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.