α,α-dibromomethyl-(3,4-dimethoxyphenyl)methanol | 115988-70-0

• 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: α,α-dibromomethyl-(3,4-dimethoxyphenyl)methanol
• 英文别名: 2,2-dibromo-1-(3,4-dimethoxyphenyl)ethanol；1-Dibromo-2-hydroxy-2-(3,4-dimethoxyphenyl)ethane
• CAS: 115988-70-0
• 化学式: C₁₀H₁₂Br₂O₃
• 分子量: 340.011
• InChiKey: CFUNERRLQGTLPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 α,α-dibromomethyl-(3,4-dimethoxyphenyl)methanol 在 氢氧化钾 作用下， 生成 2,2-dimethoxy-1-(3,4-dimethoxyphenyl)ethanol
  参考文献：
  名称：

  Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation

  摘要：

  A facile and efficient synthesis of optically active alpha-methoxyaryl acetic acids (up to 95% ee), alpha-methoxyaryl ethanols (up to 93% ee) and alpha-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, alpha-hydroxyaryl acetaldehyde acetals. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.023
• 作为产物：
  描述：

  3,4-dimethoxy-β-bromostyrene 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙腈 为溶剂， 以100%的产率得到α,α-dibromomethyl-(3,4-dimethoxyphenyl)methanol
  参考文献：
  名称：

  Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation

  摘要：

  A facile and efficient synthesis of optically active alpha-methoxyaryl acetic acids (up to 95% ee), alpha-methoxyaryl ethanols (up to 93% ee) and alpha-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, alpha-hydroxyaryl acetaldehyde acetals. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.023

文献信息

• Rapid synthesis of the tetrahydroquinoline alkaloids: angustureine, cuspareine and galipinine
  作者：Aisling O'Byrne、Paul Evans

  DOI：10.1016/j.tet.2008.06.073

  日期：2008.8

  A one-pot method for the preparation of 1,2-substituted dihydroquinolines is described. This method features the C-2 addition of a range of organolithium reagents to quinoline followed by the in-situ addition of an electrophile. Standard palladium-catalysed hydrogenation, of the resultant 1,2-disubstituted dihydroquinoline adducts, generates the corresponding 1,2-disubstituted tetrahydroquinoline. A series of such compounds have been synthesised including the natural products; (+/-)-angustureine 1, cuspareine 2 and galipinine 3. (C) 2008 Elsevier Ltd. All rights reserved.