2-methoxymethyl-α-phenylbenzyl alcohol | 108683-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxymethyl-α-phenylbenzyl alcohol
• 英文别名: [2-(Methoxymethyl)phenyl]-phenylmethanol
• CAS: 108683-08-5
• 化学式: C₁₅H₁₆O₂
• mdl: MFCD21033862
• 分子量: 228.291
• InChiKey: GGRKTBDUKKMESC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxymethyl-α-phenylbenzyl alcohol 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到(2-(methoxymethyl)phenyl)(phenyl)methanone
  参考文献：
  名称：

  A Convenient Method for the Synthesis of9-Aryl-4-methoxynaphtho[2,3-c]furan-1(3H)-ones

  摘要：

  A three-step procedure for the synthesis of the title lignan lactone derivatives is described. The route involves a tandem Michael addition/cyclization reaction between o-aroyl-alpha-methoxybenzyllithiums, which are generated in situ by the treatment of aryl 2-methoxymethylphenyl ketones with lithium diisopropylamide (LDA) in THF at -78 degrees C, and furan-2(5H)-one to give the corresponding 9-aryl-9-hydroxy-4-methoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1 (3H)-ones in moderate to good yields. These products are readily transformed into the title naphthofuranones by dehydration with thionyl. chloride in pyridine, followed by aromatization with palladium on activated carbon.

  DOI：

  10.3987/com-97-7864
• 作为产物：
  描述：

  1-溴-2-(甲氧基甲基)苯 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 生成 2-methoxymethyl-α-phenylbenzyl alcohol
  参考文献：
  名称：

  A Convenient Method for the Synthesis of9-Aryl-4-methoxynaphtho[2,3-c]furan-1(3H)-ones

  摘要：

  A three-step procedure for the synthesis of the title lignan lactone derivatives is described. The route involves a tandem Michael addition/cyclization reaction between o-aroyl-alpha-methoxybenzyllithiums, which are generated in situ by the treatment of aryl 2-methoxymethylphenyl ketones with lithium diisopropylamide (LDA) in THF at -78 degrees C, and furan-2(5H)-one to give the corresponding 9-aryl-9-hydroxy-4-methoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1 (3H)-ones in moderate to good yields. These products are readily transformed into the title naphthofuranones by dehydration with thionyl. chloride in pyridine, followed by aromatization with palladium on activated carbon.

  DOI：

  10.3987/com-97-7864

文献信息

• A Convenient Method for the Synthesis of9-Aryl-4-methoxynaphtho[2,3-c]furan-1(3H)-ones
  作者：Kazuhiro Kobayashi、Yasuhiro Kajimura、Kouji Maeda、Tomokazu Uneda、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.3987/com-97-7864

  日期：——

  A three-step procedure for the synthesis of the title lignan lactone derivatives is described. The route involves a tandem Michael addition/cyclization reaction between o-aroyl-alpha-methoxybenzyllithiums, which are generated in situ by the treatment of aryl 2-methoxymethylphenyl ketones with lithium diisopropylamide (LDA) in THF at -78 degrees C, and furan-2(5H)-one to give the corresponding 9-aryl-9-hydroxy-4-methoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1 (3H)-ones in moderate to good yields. These products are readily transformed into the title naphthofuranones by dehydration with thionyl. chloride in pyridine, followed by aromatization with palladium on activated carbon.