1-benzo[1,3]dioxol-5-yl-6,7-dimethoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline | 64881-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzo[1,3]dioxol-5-yl-6,7-dimethoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 1-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-2-(4-methylphenyl)sulfonyl-3,4-dihydro-1H-isoquinoline
• CAS: 64881-02-3
• 化学式: C₂₅H₂₅NO₆S
• 分子量: 467.543
• InChiKey: HZNORIXNEVDWOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-benzo[1,3]dioxol-5-yl-6,7-dimethoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 2.5h， 以86%的产率得到1-(3,4-methylenedioxyphenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Mild and Efficient Syntheses of 1-Aryl-3,4-dihydroisoquinolines and 1-Aryl-3,4-dihydro-β-carbolines via Regiospecific β-Eliminations of the CorrespondingN-Tosyl-1,2,3,4-tetrahydroisoquinolines andN-Tosyl-1,2,3,4-tetrahydro-β-carbolines

  摘要：

  Treatment of N-tosyl-1-aryl-1,2,3,4-tetrahydro-isoquinolines or N-tosyl-1-aryl-1, 2,3,4-tetrahydro-beta-carbolines with a strong base such as NaOH or KOH at 70 degrees C in dimethylsulfoxide (DMSO) produced 1-aryl-3,4-dihydroisoquinolines or 1-aryl-3,4-dihydro-beta-carbolines in good yields via mild and regiospecific beta-eliminations. A dramatic solvent effect was observed, DMSO was crucial for the reactions. The temperature is also crucial for the reactions and should be kept between 60 and 80 degrees C.

  DOI：

  10.1080/00397911.2011.568659
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 吡啶 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 1-benzo[1,3]dioxol-5-yl-6,7-dimethoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  Ito,K.; Tanaka,H., Chemical and pharmaceutical bulletin, 1977, vol. 25, # 7, p. 1732 - 1739

  摘要：

  DOI：

文献信息

• Efficient and Practical One-Pot Conversions of N-Tosyltetrahydroisoquinolines into Isoquinolines and of N-Tosyltetrahydro-β-carbolines into β-Carbolines through Tandem β-Elimination and Aromatization
  作者：Jing Dong、Xiao-Xin Shi、Jing-Jing Yan、Jing Xing、Qiang Zhang、Sen Xiao

  DOI：10.1002/ejoc.201001153

  日期：2010.12

  An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into β-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-β-carbolines as intermediates, and these were then oxidized in situ by

  描述了一种将 N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) 转化为异喹啉和将 N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) 转化为 β-咔啉的有效、实用和通用的方法。在二甲基亚砜中用碱处理 N-tosyl-THIQs 或 N-tosyl-THBCs 得到作为中间体的二氢异喹啉或二氢-β-咔啉，然后这些被分子氧原位氧化得到异喹啉或 β-咔啉。产量。两种一锅法转化都是通过串联β-消除和芳构化发生的。
• ITO K.; TANAKA H., CHEM. AND PHARM. BULL. <CPBT-AL>, 1977, 25, NO 7, 1732-1739
  作者：ITO K.、 TANAKA H.

  DOI：——

  日期：——
• Mild and Efficient Syntheses of 1-Aryl-3,4-dihydroisoquinolines and 1-Aryl-3,4-dihydro-β-carbolines via Regiospecific β-Eliminations of the Corresponding<i>N</i>-Tosyl-1,2,3,4-tetrahydroisoquinolines and<i>N</i>-Tosyl-1,2,3,4-tetrahydro-β-carbolines
  作者：Jing Dong、Xiao-Xin Shi、Jing Xing、Jing-Jing Yan

  DOI：10.1080/00397911.2011.568659

  日期：2012.10

  Treatment of N-tosyl-1-aryl-1,2,3,4-tetrahydro-isoquinolines or N-tosyl-1-aryl-1, 2,3,4-tetrahydro-beta-carbolines with a strong base such as NaOH or KOH at 70 degrees C in dimethylsulfoxide (DMSO) produced 1-aryl-3,4-dihydroisoquinolines or 1-aryl-3,4-dihydro-beta-carbolines in good yields via mild and regiospecific beta-eliminations. A dramatic solvent effect was observed, DMSO was crucial for the reactions. The temperature is also crucial for the reactions and should be kept between 60 and 80 degrees C.
• Ito,K.; Tanaka,H., Chemical and pharmaceutical bulletin, 1977, vol. 25, # 7, p. 1732 - 1739
  作者：Ito,K.、Tanaka,H.

  DOI：——

  日期：——