3-(2-hydroxyphenyl)-1-(thiophen-2-yl)propan-1-one | 1330048-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-hydroxyphenyl)-1-(thiophen-2-yl)propan-1-one
• 英文别名: 3-(2-Hydroxyphenyl)-1-thiophen-2-ylpropan-1-one；3-(2-hydroxyphenyl)-1-thiophen-2-ylpropan-1-one
• CAS: 1330048-57-1
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: FSVIEVITZPEKMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxyphenyl)-1-(thiophen-2-yl)propan-1-one 在 potassium carbonate 、 对甲苯磺酰肼 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到2-(thiophen-2-yl)chroman
  参考文献：
  名称：

  Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans

  摘要：

  Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.027
• 作为产物：
  描述：

  3-(2-thienyl)-1-(2-hydroxyphenyl)-2-propen-1-one 在 sodium tetrahydroborate 、 chloroauric acid 、 水 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 24.0h， 生成 3-(2-hydroxyphenyl)-1-(thiophen-2-yl)propan-1-one
  参考文献：
  名称：

  An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4

  摘要：

  2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.117

文献信息

• An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4
  作者：Gourhari Maiti、Utpal Kayal、Rajiv Karmakar、Rudraksha N. Bhattacharya

  DOI：10.1016/j.tetlet.2012.08.117

  日期：2012.11

  2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.
• Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans
  作者：Xuyang Shang、Xiaomeng Zhou、Wei Zhang、Changfeng Wan、Junmin Chen

  DOI：10.1016/j.tet.2015.08.027

  日期：2015.10

  Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable. (C) 2015 Elsevier Ltd. All rights reserved.