4-(3-methoxyphenylthio)-2,2-dimethyl-2H-chromene-3-carbaldehyde | 1343414-77-6

• 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: 4-(3-methoxyphenylthio)-2,2-dimethyl-2H-chromene-3-carbaldehyde
• CAS: 1343414-77-6
• 化学式: C₁₉H₁₈O₃S
• 分子量: 326.416
• InChiKey: LAKCEOJBNUGCPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(3-methoxyphenylthio)-2,2-dimethyl-2H-chromene-3-carbaldehyde 在 iron(III) chloride 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 10-methoxy-6,6,7-trimethyl-6,7-dihydrothiochromeno[3,2-c]chromene
  参考文献：
  名称：

  An efficient synthesis of 6H,7H-chromeno[4,3-b]chromenes and 6,7-dihydrothio chromeno[3,2-c]chromenes as 9-substituted xanthene like analogs

  摘要：

  An efficient synthetic route with good overall yields to access 7-aryl/heteroaryl/alkyl substituted 6H,7H-chromeno[4,3-b]chromene, and 6,7-dihydrothiochromeno[3,2-c]chromene scaffolds has been developed. The route to these xanthene-like analogs involves a three-step reaction sequence: (1) Michael addition of readily available phenol and thiophenol to 4-chloro-2,2-dimethyl-2H-chromene-3-carbaldehyde, (2) Grignard reaction of different aryl, heteroaryl and alkyl magnesium bromides on the resulting carbaldehydes followed by (3) FeCl3 catalyzed spontaneous intramolecular Friedel-Craft's reaction on the diarylmethyl carbinols. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.127
• 作为产物：
  描述：

  2,2-二甲基-苯并二氢吡喃-4-酮 在 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 25.5h， 生成 4-(3-methoxyphenylthio)-2,2-dimethyl-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  An efficient synthesis of 6H,7H-chromeno[4,3-b]chromenes and 6,7-dihydrothio chromeno[3,2-c]chromenes as 9-substituted xanthene like analogs

  摘要：

  An efficient synthetic route with good overall yields to access 7-aryl/heteroaryl/alkyl substituted 6H,7H-chromeno[4,3-b]chromene, and 6,7-dihydrothiochromeno[3,2-c]chromene scaffolds has been developed. The route to these xanthene-like analogs involves a three-step reaction sequence: (1) Michael addition of readily available phenol and thiophenol to 4-chloro-2,2-dimethyl-2H-chromene-3-carbaldehyde, (2) Grignard reaction of different aryl, heteroaryl and alkyl magnesium bromides on the resulting carbaldehydes followed by (3) FeCl3 catalyzed spontaneous intramolecular Friedel-Craft's reaction on the diarylmethyl carbinols. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.127

文献信息

• [RuCl2(p-cymene)2]2 catalyzed cross dehydrogenative coupling (CDC) toward xanthone and fluorenone analogs through intramolecular C–H bond functionalization reaction
  作者：Sudipta Kumar Manna、Srinivas Lavanya Kumar Manda、Gautam Panda

  DOI：10.1016/j.tetlet.2014.08.062

  日期：2014.10

  A synthetic approach toward xanthone and fluorenone derivatives through ruthenium catalyzed intramolecular C-H bond functionalization using an external oxidant has been developed. In the presence of [RuCl2(p-cymene)(2)](2), a variety of substituted ortho-aryloxy/aryl benzaldehydes underwent cross dehydrogenative coupling to afford the corresponding analogs in moderate to good yields. (C) 2014 Elsevier Ltd. All rights reserved.