3-(2-hydroxyphenyl)-1-p-tolylpropan-1-one | 1329810-25-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(2-hydroxyphenyl)-1-p-tolylpropan-1-one
• 英文别名: 3-(2-Hydroxyphenyl)-1-(4-methylphenyl)propan-1-one；3-(2-hydroxyphenyl)-1-(4-methylphenyl)propan-1-one
• CAS: 1329810-25-4
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: HXXPXRMLFNLMBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxyphenyl)-1-p-tolylpropan-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81%的产率得到2-(4-methylphenyl)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：

  2-hydroxy-4'-methyl-chalcone 在 三乙基硅烷 、 indium(III) chloride 作用下， 以 乙醚 为溶剂， 以80%的产率得到3-(2-hydroxyphenyl)-1-p-tolylpropan-1-one
  参考文献：
  名称：

  通过切换溶剂，使用InCl 3 / Et 3 SiH系统一锅法合成O-杂环或芳基酮

  摘要：

  使用Int 3 SiH的Et 3 SiH通过转换溶剂进行顺序离子氢化反应，可以在InCl 3存在下实现O-杂环或芳基酮的有效一锅合成。该方法可用于轻松构建C–O键并制备共轭物还原产物，包括苯并二氢吡喃，四氢呋喃，四氢吡喃，二氢异苯并呋喃，二氢查耳酮和1,4-二酮。另外，通过实验研究证实了涉及共轭物还原和串联还原性环化的新型合理机制。

  DOI：

  10.1021/acs.joc.9b00140

文献信息

• Rh-Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A-E
  作者：Maddali L. N. Rao、Boddu S. Ramakrishna

  DOI：10.1002/ejoc.201901314

  日期：2019.12.15

  A Rh‐catalyzed decarbonylative addition of salicylaldehydes with vinyl ketones was developed for the synthesis of o‐hydroxydihydrochalcones in good yields. This protocol was applied in the synthesis of taccabulin family of natural products.

  开发了水杨醛与乙烯基酮进行Rh催化的羰基脱羰加成反应，以高收率合成邻羟基二氢查耳酮。该方案被应用于天然产物他卡布林家族的合成。
• Brønsted Acid Catalyzed Intramolecular Allylic Substitution Reaction of Allylic Alcohols: A Facile Synthesis of 2-Vinylchromans
  作者：Chang-Hua Ding、Bin Xu、Yun-Fan Li、Yu-Ting Xi、Kai-Ji Hu、Qitao Tan

  DOI：10.1055/a-2301-9223

  日期：——

  Brønsted acid catalyzed intramolecular allylic substitution reaction of secondary and tertiary allylic alcohols has been developed. A variety of 2-vinylchromans were efficiently prepared in moderate to excellent yields. The given method features wide substrate scope, operational simplicity, and mild, metal-free reaction conditions. The practicability of the method was demonstrated by a gram-scale reaction

  已开发出布朗斯台德酸催化仲烯丙醇和叔烯丙醇的分子内烯丙取代反应。多种 2-乙烯基苯并二氢吡喃以中等至优异的产率有效制备。该方法具有底物范围广、操作简单、反应条件温和、无金属等特点。通过克级反应和产物的进一步衍生证明了该方法的实用性。还对催化不对称反应进行了初步研究。
• 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.
• One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl₃/Et₃SiH System by Switching the Solvent
  作者：Wenqiang Jia、Qiumu Xi、Tianqi Liu、Minjian Yang、Yonghui Chen、Dali Yin、Xiaojian Wang

  DOI：10.1021/acs.joc.9b00140

  日期：2019.5.3

  An efficient one-pot synthesis of O-heterocycles or aryl ketones has been achieved using Et3SiH in the presence of InCl3 via a sequential ionic hydrogenation reaction by switching the solvent. This methodology can be used to construct C–O bonds and to prepare conjugate reduction products, including chromans, tetrahydrofurans, tetrahydropyrans, dihydroisobenzofurans, dihydrochalcones, and 1,4-diones

  使用Int 3 SiH的Et 3 SiH通过转换溶剂进行顺序离子氢化反应，可以在InCl 3存在下实现O-杂环或芳基酮的有效一锅合成。该方法可用于轻松构建C–O键并制备共轭物还原产物，包括苯并二氢吡喃，四氢呋喃，四氢吡喃，二氢异苯并呋喃，二氢查耳酮和1,4-二酮。另外，通过实验研究证实了涉及共轭物还原和串联还原性环化的新型合理机制。
• 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.