3-(4-isopropoxyphenyl)-7,8-dimethoxy-2-tosyl-1,2,3,4-tetrahydroisoquinoline | 1363394-54-0

• 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: 3-(4-isopropoxyphenyl)-7,8-dimethoxy-2-tosyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 7,8-dimethoxy-2-(4-methylphenyl)sulfonyl-3-(4-propan-2-yloxyphenyl)-3,4-dihydro-1H-isoquinoline
• CAS: 1363394-54-0
• 化学式: C₂₇H₃₁NO₅S
• 分子量: 481.613
• InChiKey: DPBZMVLUDRLQJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-isopropoxyphenyl)-7,8-dimethoxy-2-tosyl-1,2,3,4-tetrahydroisoquinoline 在 N-溴代丁二酰亚胺(NBS) 、 C₃₂H₂₁O₄P 、 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-bromo-4-(7,8-dimethoxy-2-tosyl-1,2,3,4-tetrahydroisoquinolin-3-yl)phenol
  参考文献：
  名称：

  Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine

  摘要：

  An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C-H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (+/-)-tetrahydropalmatine was achieved by exploiting this new transformation.

  DOI：

  10.1021/ol300180w
• 作为产物：
  描述：

  methyl 2,3-dimethoxy-6-(methoxymethoxy)benzoate 在 吡啶 、 盐酸 、 manganese(IV) oxide 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 四丁基碘化铵 、 三乙胺 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 187.0h， 生成 3-(4-isopropoxyphenyl)-7,8-dimethoxy-2-tosyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine

  摘要：

  An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C-H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (+/-)-tetrahydropalmatine was achieved by exploiting this new transformation.

  DOI：

  10.1021/ol300180w

文献信息

• Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine
  作者：Keiji Mori、Taro Kawasaki、Takahiko Akiyama

  DOI：10.1021/ol300180w

  日期：2012.3.16

  An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C-H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (+/-)-tetrahydropalmatine was achieved by exploiting this new transformation.