1-(4'-methoxyphenyl)acetoxy-2-methoxy-5-cyanomethylphenyl | 162470-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 1-(4'-methoxyphenyl)acetoxy-2-methoxy-5-cyanomethylphenyl
• 英文别名: [5-(Cyanomethyl)-2-methoxyphenyl] 2-(4-methoxyphenyl)acetate
• CAS: 162470-42-0
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: XUHGISSJGALWDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4'-methoxyphenyl)acetoxy-2-methoxy-5-cyanomethylphenyl 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 生成 (3-acetoxy-4-methoxy-phenyl)-acetonitrile
  参考文献：
  名称：

  光化学合成7,8-双加氧异喹啉生物碱

  摘要：

  报道了一种基于由3-羟基-4-甲氧基苯基乙腈衍生的酯的弗里斯-弗里斯重排而合成7,8-二加氧四氢异喹啉碱生物碱的新方法。该方法适用于生物碱Arizonine和1 -2-berbine生物碱的1-苄基四氢异喹啉碱的合成。

  DOI：

  10.1016/0040-4039(94)02448-k
• 作为产物：
  描述：

  3-hydroxy-4-methoxyphenylacetonitrile 、 4-甲氧基苯乙酰氯 在 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以76%的产率得到1-(4'-methoxyphenyl)acetoxy-2-methoxy-5-cyanomethylphenyl
  参考文献：
  名称：

  Syntheses of dopaminergic 1-cyclohexylmethyl-7,8-dioxygenated tetrahydroisoquinolines by selective heterogeneous tandem hydrogenation

  摘要：

  We describe the preparation in a 'one-pot' sequence I-cyclohexylmethyl 7,8-dioxygenated tetrahydroisoquinoline, substituted and unsubstituted in the C ring by application of the Photo-Fries transposition, followed by a tandem reduction-cyclization and further reduction. Indeed, we have accomplished for the first time regioselective hydrogenation of the benzylic ring of the tetrahydroisoquinoline systems. All I-cyclohexylmethyl THIQ synthesized were able to displace D-2 dopamine receptor from its specific binding site in rat striatal membranes, while the N-methylated derivatives showed also affinity for D-1 dopamine receptors. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)01403-5

文献信息

• Syntheses of dopaminergic 1-cyclohexylmethyl-7,8-dioxygenated tetrahydroisoquinolines by selective heterogeneous tandem hydrogenation
  作者：Inmaculada Andreu、Nuria Cabedo、Gregorio Torres、Abdeslam Chagraoui、M Carmen Ramı́rez de Arellano、Salvador Gil、Almudena Bermejo、Marı́a Valpuesta、Philippe Protais、Diego Cortes

  DOI：10.1016/s0040-4020(02)01403-5

  日期：2002.12

  We describe the preparation in a 'one-pot' sequence I-cyclohexylmethyl 7,8-dioxygenated tetrahydroisoquinoline, substituted and unsubstituted in the C ring by application of the Photo-Fries transposition, followed by a tandem reduction-cyclization and further reduction. Indeed, we have accomplished for the first time regioselective hydrogenation of the benzylic ring of the tetrahydroisoquinoline systems. All I-cyclohexylmethyl THIQ synthesized were able to displace D-2 dopamine receptor from its specific binding site in rat striatal membranes, while the N-methylated derivatives showed also affinity for D-1 dopamine receptors. (C) 2002 Published by Elsevier Science Ltd.
• Photochemical synthesis of 7,8-dioxygenated isoquinoline alkaloids
  作者：Rafael Suau、María Valpuesta、Gregorio Torres

  DOI：10.1016/0040-4039(94)02448-k

  日期：1995.2

  A new approach to the synthesis of 7,8-dioxygenated tetrahydroisoquinoline alkaloids based on the phot-Fries rearrangement of esters derived from 3-hydroxy-4-methoxy phenylacetonitrile is reported. The procedure was applied to the synthesis of the alkaloid Arizonine and 1-benzyl tetrahydroisoquinoline precursor of cularine and 1,2-berbine alkaloids.

  报道了一种基于由3-羟基-4-甲氧基苯基乙腈衍生的酯的弗里斯-弗里斯重排而合成7,8-二加氧四氢异喹啉碱生物碱的新方法。该方法适用于生物碱Arizonine和1 -2-berbine生物碱的1-苄基四氢异喹啉碱的合成。