1-(4-fluorophenyl)-6,7-dimethoxyisochroman | 893775-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-(4-fluorophenyl)-6,7-dimethoxyisochroman
• 英文别名: 1-(4-fluorophenyl)-6,7-dimethoxy-3,4-dihydro-1H-isochromene
• CAS: 893775-86-5
• 化学式: C₁₇H₁₇FO₃
• 分子量: 288.319
• InChiKey: ASCKBZIIPAEFJW-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  398.0±42.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-6,7-dimethoxyisochroman 在 chromium(VI) oxide 、 硫酸 、 一水合肼 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 1-(4-Fluorophenyl)-7,8-dimethoxy-3,5-dihydro-2,3-benzodiazepin-4-one
  参考文献：
  名称：

  Design and development of 2,3-benzodiazepine (CFM) noncompetitive AMPA receptor antagonists

  摘要：

  2,3-Benzodiazepines represent a class of heterocyclic compounds that interact with AMPA-type glutamate receptors in a noncompetitive manner. These compounds have attracted great interest for their pharmacological effects against acute and chronic neurodegenerative diseases, such as ischemia and epilepsy. We synthesized a large number of 2,3-benzodiazepine derivatives, which showed anticonvulsant properties in different seizure models and a noncompetitive blockade of AMPA receptor. This article will briefly mention our work in this field and the main SAR considerations. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01186-7
• 作为产物：
  描述：

  对氟苯甲醛 、 3,4-二甲氧基苯乙醇 在 2H⁽¹⁺⁾*Mo₁₂O₄₀P^(3-)*C₈H₁₄NOS⁽¹⁺⁾ 作用下， 反应 0.33h， 以95%的产率得到1-(4-fluorophenyl)-6,7-dimethoxyisochroman
  参考文献：
  名称：

  杂多酸离子液体在碳酸二甲酯中通过oxa-Pictet-Spengler环化非均相催化合成异色满

  摘要：

  基于 Keggin 型多金属氧酸盐 (H 3 PMo 12 O 40 ) 和维生素 B1 类似物 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium (HEMT)合成的可回收且高效的多相绿色催化剂)，即制备[HEMTH]H 2 [PMo 12 O 40 ]。使用碳酸二甲酯 (DMC) 作为绿色溶剂，催化芳基乙醇和醛的 Oxa-Pictet-Spengler 环化，在中等条件下以优异的收率提供各种取代的异色烷。此外，该协议适用于克级反应，催化剂可以循环使用八次，而不会显着丧失活性。

  DOI：

  10.1039/d1ra01004b

文献信息

• Oxa-Pictet–Spengler reaction in water. Synthesis of some (±)-1-aryl-6,7-dimethoxyisochromans
  作者：Aamer Saeed

  DOI：10.1016/j.cclet.2009.11.009

  日期：2010.3

  Abstract An acid catalyzed oxa-Pictet–Spengler reaction ‘on water’ leading to the synthesis of a variety of 1-aryl-6,7-dimethoxyisochromans is described. The aqueous chemistry is a much cleaner, efficient, cheaper and simple method for synthesis. The scope of reactions was extended to thia-Pictet–Spengler reaction to afford the some isothiochromans.

  摘要描述了一种酸催化的“ oxa-Pictet-Spengler反应在水上”反应，该反应导致合成各种1-芳基-6,7-二甲氧基异色满。水性化学物质是一种更清洁，有效，便宜且简单的合成方法。反应范围扩大到了硫杂-皮格特-斯宾格勒反应，得到了一些异硫氰酸盐。
• Synthesis of isochromans via Fe(OTf)2-catalyzed Oxa-Pictet–Spengler cyclization
  作者：Jimei Zhou、Chao Wang、Dong Xue、Weijun Tang、Jianliang Xiao、Chaoqun Li

  DOI：10.1016/j.tet.2018.10.028

  日期：2018.12

  Fe(OTf)2 has been found to be an efficient catalyst for the Oxa-Pictet–Spengler cyclization reaction leading to isochromans. A series of substituted isochromans were obtained with good to excellent isolated yields by coupling β-arylethanols with aldehydes or ketals under the catalysis of 1 mol% of Fe(OTf)2 at 70 °C. Using a cheap, less-toxic catalyst with water as the only byproduct, this iron-catalyzed

  已发现Fe（OTf）2是导致异色团的Oxa-Pictet-Spengler环化反应的有效催化剂。通过 在70℃下1摩尔％的Fe（OTf）2催化下，将β-芳基乙醇与醛或缩酮偶联，可以得到一系列具有良好分离效果的取代异色满。使用廉价的，毒性较小的催化剂，水是唯一的副产物，这种铁催化的Oxa-Pictet-Spengler反应可以被认为对环境友好且经济实惠。
• Design and development of 2,3-benzodiazepine (CFM) noncompetitive AMPA receptor antagonists
  作者：Rosaria Gitto、Maria Zappalà、Giovambattista De Sarro、Alba Chimirri

  DOI：10.1016/s0014-827x(01)01186-7

  日期：2002.2

  2,3-Benzodiazepines represent a class of heterocyclic compounds that interact with AMPA-type glutamate receptors in a noncompetitive manner. These compounds have attracted great interest for their pharmacological effects against acute and chronic neurodegenerative diseases, such as ischemia and epilepsy. We synthesized a large number of 2,3-benzodiazepine derivatives, which showed anticonvulsant properties in different seizure models and a noncompetitive blockade of AMPA receptor. This article will briefly mention our work in this field and the main SAR considerations. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Heteropolyacid ionic liquid heterogeneously catalyzed synthesis of isochromans <i>via</i> oxa-Pictet–Spengler cyclization in dimethyl carbonate
  作者：Guoping Yang、Ke Li、Kai Zeng、Yijin Li、Tao Yu、Yufeng Liu

  DOI：10.1039/d1ra01004b

  日期：——

  3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium (HEMT), i.e., [HEMTH]H2[PMo12O40] was prepared. Oxa-Pictet–Spengler cyclization of arylethanols and aldehydes were catalyzed to afford various substituted isochromans in moderate conditions with excellent yields using dimethyl carbonate (DMC) as a green solvent. Furthermore, this protocol was applicable in a gram-scale reaction, and the catalyst could

  基于 Keggin 型多金属氧酸盐 (H 3 PMo 12 O 40 ) 和维生素 B1 类似物 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium (HEMT)合成的可回收且高效的多相绿色催化剂)，即制备[HEMTH]H 2 [PMo 12 O 40 ]。使用碳酸二甲酯 (DMC) 作为绿色溶剂，催化芳基乙醇和醛的 Oxa-Pictet-Spengler 环化，在中等条件下以优异的收率提供各种取代的异色烷。此外，该协议适用于克级反应，催化剂可以循环使用八次，而不会显着丧失活性。