3-isopropoxy-4-methoxy-β-nitrostyrene | 1213240-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-isopropoxy-4-methoxy-β-nitrostyrene
• 英文别名: 1-methoxy-4-(2-nitroethenyl)-2-propan-2-yloxybenzene
• CAS: 1213240-88-0
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: YTFURKLVKBBCQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-isopropoxy-4-methoxy-β-nitrostyrene 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 silica gel 、 四氯化钛 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 异丙醇 为溶剂， 反应 16.5h， 生成 7-甲氧基-1,2,3,4-四氢异喹啉-6-醇
  参考文献：
  名称：

  Isolation, Structure Characterization, and Synthesis of Stabilized 1,2,3,4-Tetrahydroisoquinoline Marine Natural Product from Potassium Cyanide Pretreated Thai Tunicate, Ecteinascidia thurstoni

  摘要：

  A simple 1,2,3,4-tetrahydroisoquinoline marine natural product (2a) together with two known compounds (3 and 4) was isolated from a low polar fraction of the crude extract of KCN pretreated Thai tunicate Ecteinascidia thurstoni. The structure of 2a was determined by X-ray crystallographic analysis. We also reported an eight-step large-scale preparation of 2a from isovanillin (9).

  DOI：

  10.3987/com-13-s(s)32
• 作为产物：
  描述：

  异香兰素 在 ammonium acetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-isopropoxy-4-methoxy-β-nitrostyrene
  参考文献：
  名称：

  C-1 Alkynylation of N-Methyltetrahydroisoquinolines through CDC: A Direct Access to Phenethylisoquinoline Alkaloids

  摘要：

  本文介绍了一种使用CuI-DEAD的N-甲基四氢异喹啉与炔烃之间的直接交叉偶联反应，该反应以高产率选择性地生成了C-1位炔基化的产物。这种区域选择性与先前报道的N,N-二甲基苄胺反应结果形成鲜明对比，后者几乎完全或主要生成N-甲基炔基化产物。C-1位取代的丙炔基异喹啉能通过Pd/C催化轻易还原为苯乙基异喹啉。这一反应序列提供了一条合成甲氧啡啉、同劳丹诺素及其他苯乙基异喹啉生物碱的简捷途径。

  DOI：

  10.1055/s-0031-1290532

文献信息

• C-1 Alkynylation of N-Methyltetrahydroisoquinolines through CDC: A Direct Access to Phenethylisoquinoline Alkaloids
  作者：Kamal Singh、Paramjit Singh、Amarjit Kaur、Pushpinder Singh

  DOI：10.1055/s-0031-1290532

  日期：2012.3

  Direct cross-coupling between N-methyltetrahydroisoquinolines and alkynes using CuI-DEAD is presented. It affords the regioselective C-1-alkynylated products in good yield. This regio­selectivity is in contrast to the results reported earlier in the reaction of N,N-dimethylbenzyl amine where the N-methyl alkynylated product was formed exclusively or predominantly. The C-1-substituted propargylic isoquinolines were easily reduced to phenethylisoquinolines with Pd/C. This reaction sequence provides a short route to synthesize methopholine, homolaudanosine and other phenethylisoquinoline alkaloids.

  本文介绍了一种使用CuI-DEAD的N-甲基四氢异喹啉与炔烃之间的直接交叉偶联反应，该反应以高产率选择性地生成了C-1位炔基化的产物。这种区域选择性与先前报道的N,N-二甲基苄胺反应结果形成鲜明对比，后者几乎完全或主要生成N-甲基炔基化产物。C-1位取代的丙炔基异喹啉能通过Pd/C催化轻易还原为苯乙基异喹啉。这一反应序列提供了一条合成甲氧啡啉、同劳丹诺素及其他苯乙基异喹啉生物碱的简捷途径。
• Novel hybrids from lamellarin D and combretastatin A 4 as cytotoxic agents
  作者：Li Shen、Xiaochun Yang、Bo Yang、Qiaojun He、Yongzhou Hu

  DOI：10.1016/j.ejmech.2009.09.017

  日期：2010.1

  A new series of hybrids of lamellarin D and combretastatin A 4,1,2-diphenyl-5,6-dihydropyrrolo [2,1-a] isoquinolines, were designed as cytotoxic agents based on principles of combination in medicinal chemistry and taking the parent compounds' different anti-proliferative mechanisms into consideration. Twenty-two novel hybrids were synthesized through a convenient route, with a key step of core pyrrole formation and evaluated for their anti-proliferative activities in vitro against K-562, A-549, SMMC-7721, SGC-7901 and HCF-116 cancer cell lines. The results showed that some hybrids had good anti-proliferative activities in low IC50 ranges. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Isolation, Structure Characterization, and Synthesis of Stabilized 1,2,3,4-Tetrahydroisoquinoline Marine Natural Product from Potassium Cyanide Pretreated Thai Tunicate, Ecteinascidia thurstoni
  作者：Naoki Saito、Khanit Suwanborirux、Shinya Kimura、Waree Pangkruang、Masashi Yokoya、Amane Honda、Ploenthip Puthongking

  DOI：10.3987/com-13-s(s)32

  日期：——

  A simple 1,2,3,4-tetrahydroisoquinoline marine natural product (2a) together with two known compounds (3 and 4) was isolated from a low polar fraction of the crude extract of KCN pretreated Thai tunicate Ecteinascidia thurstoni. The structure of 2a was determined by X-ray crystallographic analysis. We also reported an eight-step large-scale preparation of 2a from isovanillin (9).