3,4-dimethoxy-6-iodo-N-methyl-N-(6,7-methylenedioxy-1-naphthyl)benzamide | 219782-01-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-dimethoxy-6-iodo-N-methyl-N-(6,7-methylenedioxy-1-naphthyl)benzamide
• 英文别名: 2-iodo-4,5-dimethoxy-N-methyl-N-(6,7-methylenedioxy-1-naphthyl)benzamide；N-benzo[f][1,3]benzodioxol-5-yl-2-iodo-4,5-dimethoxy-N-methylbenzamide
• CAS: 219782-01-1
• 化学式: C₂₁H₁₈INO₅
• 分子量: 491.282
• InChiKey: HXRUSSPERKFKOD-UHFFFAOYSA-N

物化性质

• 沸点：
  625.782±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.626±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxy-6-iodo-N-methyl-N-(6,7-methylenedioxy-1-naphthyl)benzamide 在 palladium diacetate 三(邻甲基苯基)磷 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以89%的产率得到oxynitidine
  参考文献：
  名称：

  Concise Synthesis of Nitidine by Palladium-assisted Biaryl Coupling Reaction

  摘要：

  Formal total synthesis of nitidine (1) was accomplished via oxynitidine (7) by the internal aryl-aryl coupling reaction of iodo-amide (6) using palladium-assisted cyclization reaction.

  DOI：

  10.3987/com-98-s15
• 作为产物：
  描述：

  4,5-dimethoxy-2-iodobenzoyl chloride 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 3,4-dimethoxy-6-iodo-N-methyl-N-(6,7-methylenedioxy-1-naphthyl)benzamide
  参考文献：
  名称：

  Concise Synthesis of Nitidine by Palladium-assisted Biaryl Coupling Reaction

  摘要：

  Formal total synthesis of nitidine (1) was accomplished via oxynitidine (7) by the internal aryl-aryl coupling reaction of iodo-amide (6) using palladium-assisted cyclization reaction.

  DOI：

  10.3987/com-98-s15

文献信息

• Synthesis of Benzo[<b><i>c</i></b>]Phenanthridine Alkaloids, Using a Novel Palladium-Phosphine Combination System - Pd(OAc)₂, DPPP, and Bu₃P
  作者：Takashi Harayama、Toshihiko Akiyama、Yuichiro Nakano、Kentaro Shibaike、Hisashi Akamatsu、Akihiro Hori、Hitoshi Abe、Yasuo Takeuchi

  DOI：10.1055/s-2002-19799

  日期：——

  Total synthesis of several benzo[c]phenanthridine alkaloids was accomplished via an aryl-aryl coupling reaction using a novel Pd reagent prepared from Pd(OAc) 2 , DPPP, and Bu 3 P. This is a versatile method for the coupling reactions of not only aryl triflates and arenes hut also aryl halides and arenes.

  使用由 Pd(OAc) 2 、DPPP 和 Bu 3 P 制备的新型 Pd 试剂，通过芳基-芳基偶联反应完成了几种苯并[c]菲啶生物碱的全合成。只有芳基三氟甲磺酸酯和芳烃，还有芳基卤化物和芳烃。
• Aryl-Aryl Coupling Reaction Catalyzed by a Palladium Reagent Prepared from Pd(OAc)2 and n-Bu3P
  作者：Takashi Harayama、Akihiro Hori、Yuichiro Nakano、Toshihiko Akiyama、Hitoshi Abe、Yasuo Takeuchi

  DOI：10.3987/com-01-s(m)3

  日期：——

  A palladium reagent prepared from Pd (OAc)(2) (0.2 eq) and n-Bu3P (0.6 eq) catalyzed an aryl-aryl coupling reaction. This procedure is effective for coupling reactions of aryl triflate possessing no oxygen groups with arene, and of aryl iodide with arene.
• Synthesis of Benzo[c]phenanthridine Alkaloids, Chelerythrine and Nitidine, Using a Novel Palladium-Phosphine Combination System - Pd(OAc)2, DPPP, and Bu3P -
  作者：Takashi Harayama、Toshihiko Akiyama、Yuichiro Nakano、Kentaro Shibaike

  DOI：10.3987/com-98-8284

  日期：——

  Total synthesis of chelerythrine (1) and nitidine (4) was accomplished via the aryl-aryl cyclization reaction using a novel Pd reagent prepared from Pd(OAc)(2), DPPP, and Bu3P. The present method was very versatile for coupling reaction not only between aromatic triflate and arene but also between aromatic halide and arene.