5-bromo-2-hydroxy-2-phenyl-3,4-dihydronaphthalen-1(2H)-one | 1354727-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-bromo-2-hydroxy-2-phenyl-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 5-Bromo-2-hydroxy-2-phenyl-3,4-dihydronaphthalen-1-one；5-bromo-2-hydroxy-2-phenyl-3,4-dihydronaphthalen-1-one
• CAS: 1354727-94-8
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: GFQXHFXHJDGBFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  5-bromo-2-hydroxy-2-phenyl-3,4-dihydronaphthalen-1(2H)-one 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以71%的产率得到5-Bromo-2-phenylnaphthalen-1-ol
  参考文献：
  名称：

  Synthesis of substituted α-tetralones and substituted 1-naphthols via regioselective ring expansion of 1-acyl-1-indanol skeleton

  摘要：

  Substituted 1-acyl-1-indanols were prepared using the corresponding readily commercially available substituted indanones as starting materials. Treatment of each 1-acyl-1-indanol derivative with sodium methoxide in hot methanol furnished a regiospecific 2-hydroxy-alpha-tetralone derivative, which was an alpha-keto rearrangement product. Each substituted 2-hydroxy-alpha-tetralone then underwent dehydration to afford the corresponding 1-naphthol derivative. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.103
• 作为产物：
  描述：

  4-溴-1-茚酮 在 sodium hypochlorite 、 四氧化锇 、 正丁基锂 、 2,2,6,6-四甲基哌啶氧化物 、 十二/十四烷基二甲基氧化胺 、 水 、 sodium methylate 、 碳酸氢钠 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 42.75h， 生成 5-bromo-2-hydroxy-2-phenyl-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Synthesis of substituted α-tetralones and substituted 1-naphthols via regioselective ring expansion of 1-acyl-1-indanol skeleton

  摘要：

  Substituted 1-acyl-1-indanols were prepared using the corresponding readily commercially available substituted indanones as starting materials. Treatment of each 1-acyl-1-indanol derivative with sodium methoxide in hot methanol furnished a regiospecific 2-hydroxy-alpha-tetralone derivative, which was an alpha-keto rearrangement product. Each substituted 2-hydroxy-alpha-tetralone then underwent dehydration to afford the corresponding 1-naphthol derivative. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.103

文献信息

• In(OTf)3 catalyzed regioselective acyloin rearrangement of 1-acyl-1-indanols
  作者：Zhe-Yao Huang、Hong Yang、Zi-Yu Jiang、Lin Zhou、Qing-Han Li、Zhi-Gang Zhao

  DOI：10.1016/j.tetlet.2022.153987

  日期：2022.8

  A highly regioselective catalytic acyloin rearrangement of 1-acyl-1-indanols has been successfully developed. A series of α-hydroxyl carbonyl derivatives have been obtained in moderate to good yields (up to 91%) in the presence of 5 mol% of In(OTf)3.

  1-酰基-1-茚满醇的高度区域选择性催化偶氨酸重排已被成功开发。在 5 mol% 的 In(OTf) 3存在下，一系列 α-羟基羰基衍生物以中等至良好的产率（高达 91%）获得。
• Synthesis of substituted α-tetralones and substituted 1-naphthols via regioselective ring expansion of 1-acyl-1-indanol skeleton
  作者：Te-Fang Yang、Kuan-Yu Wang、Hsuan-Wei Li、Yang-Chan Tseng、Tai-Chen Lien

  DOI：10.1016/j.tetlet.2011.11.103

  日期：2012.2

  Substituted 1-acyl-1-indanols were prepared using the corresponding readily commercially available substituted indanones as starting materials. Treatment of each 1-acyl-1-indanol derivative with sodium methoxide in hot methanol furnished a regiospecific 2-hydroxy-alpha-tetralone derivative, which was an alpha-keto rearrangement product. Each substituted 2-hydroxy-alpha-tetralone then underwent dehydration to afford the corresponding 1-naphthol derivative. (C) 2011 Elsevier Ltd. All rights reserved.