2-(hydroxymethyl)-2'-methoxy-5,5-dimethyl-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one | 1424289-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(hydroxymethyl)-2'-methoxy-5,5-dimethyl-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one
• 英文别名: 2-(Hydroxymethyl)-3-(2-methoxyphenyl)-5,5-dimethylcyclohex-2-en-1-one；2-(hydroxymethyl)-3-(2-methoxyphenyl)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 1424289-38-2
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: SWNZYAPFBAFKDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-2'-methoxy-5,5-dimethyl-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 14.08h， 以69%的产率得到5-methoxy-3,3-dimethyl-4,9-dihydro-2H-fluoren-1-one
  参考文献：
  名称：

  Approach to the core structure of abeo-abietanes and gibberellins via Stork–Danheiser sequence followed by Friedel–Crafts alkylations

  摘要：

  A mild and efficient protocol for the synthesis of [6,5,6]-tricyclic framework (4) of abeo-abietanes (1) and gibberellins (2) via Stork-Danheiser sequence on a bicyclic vinylogous ester followed by Lewis acid-catalyzed Friedel-Crafts alkylations of 3-aryl-2-hydroxymethyl-2-cyclohexenones (5) is developed. A variety of 2-cyclohexenone derivatives (5) underwent smooth Friedel-Crafts alkylations to craft the [6,5,6]-tricyclic skeleton (4) in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.002
• 作为产物：
  描述：

  7,7-dimethyl-7,8-dihydro-4H-benzo[d][1,3]dioxin-5(6H)-one 、 2-Methoxyphenylmagnesium bromide 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以68%的产率得到2-(hydroxymethyl)-2'-methoxy-5,5-dimethyl-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one
  参考文献：
  名称：

  Approach to the core structure of abeo-abietanes and gibberellins via Stork–Danheiser sequence followed by Friedel–Crafts alkylations

  摘要：

  A mild and efficient protocol for the synthesis of [6,5,6]-tricyclic framework (4) of abeo-abietanes (1) and gibberellins (2) via Stork-Danheiser sequence on a bicyclic vinylogous ester followed by Lewis acid-catalyzed Friedel-Crafts alkylations of 3-aryl-2-hydroxymethyl-2-cyclohexenones (5) is developed. A variety of 2-cyclohexenone derivatives (5) underwent smooth Friedel-Crafts alkylations to craft the [6,5,6]-tricyclic skeleton (4) in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.002

文献信息

• Approach to the core structure of abeo-abietanes and gibberellins via Stork–Danheiser sequence followed by Friedel–Crafts alkylations
  作者：Badrinath N. Kakde、Subhajit Bhunia、Alakesh Bisai

  DOI：10.1016/j.tetlet.2013.01.002

  日期：2013.3

  A mild and efficient protocol for the synthesis of [6,5,6]-tricyclic framework (4) of abeo-abietanes (1) and gibberellins (2) via Stork-Danheiser sequence on a bicyclic vinylogous ester followed by Lewis acid-catalyzed Friedel-Crafts alkylations of 3-aryl-2-hydroxymethyl-2-cyclohexenones (5) is developed. A variety of 2-cyclohexenone derivatives (5) underwent smooth Friedel-Crafts alkylations to craft the [6,5,6]-tricyclic skeleton (4) in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.