2-(2-bromo-6-methoxy-4-methylphenyl)ethanol | 630120-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-bromo-6-methoxy-4-methylphenyl)ethanol
• CAS: 630120-22-8
• 化学式: C₁₀H₁₃BrO₂
• 分子量: 245.116
• InChiKey: MRABZXWVGHJVIN-UHFFFAOYSA-N

物化性质

• 沸点：
  315.7±37.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-(2-bromo-6-methoxy-4-methylphenyl)ethanol 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 四氧化锇 、 N-甲基吲哚酮 、 叔丁基锂 、 二异丁基氢化铝 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 、 叔丁醇 为溶剂， 反应 156.25h， 生成 (3aR,4R,5S)-4,5-bis(tert-butyldimethylsilanyloxy)-1-isopropyl-6-methoxy-3a,8-dimethyl-4,5-dihydro-3aH-cyclopenta[a]naphthalene
  参考文献：
  名称：

  Synthesis of natural (−)-hamigeran B

  摘要：

  Alkylation of lactam 10, first with iodide 15 and then with MeI, gave mainly (18:1) lactam 18. This was converted by treatment with t-BuLi and then with aqueous base into enone 4, which was elaborated into (-)-hamigeran B. A key feature of the last part of the synthesis is the use of t-BuMe2Si-groups (as in intermediate 24) both to direct hydrogenation from the appropriate face and to protect the benzylic C-O bond from hydrogenolysis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.089
• 作为产物：
  描述：

  2-bromo-6-methoxy-4-methylbenzaldehyde 在 9-borabicyclo[3.3.1]nonane dimer 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.5h， 生成 2-(2-bromo-6-methoxy-4-methylphenyl)ethanol
  参考文献：
  名称：

  Synthesis of natural (−)-hamigeran B

  摘要：

  Alkylation of lactam 10, first with iodide 15 and then with MeI, gave mainly (18:1) lactam 18. This was converted by treatment with t-BuLi and then with aqueous base into enone 4, which was elaborated into (-)-hamigeran B. A key feature of the last part of the synthesis is the use of t-BuMe2Si-groups (as in intermediate 24) both to direct hydrogenation from the appropriate face and to protect the benzylic C-O bond from hydrogenolysis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.089

文献信息

• Synthesis of natural (−)-hamigeran B
  作者：Derrick L.J. Clive、Jian Wang

  DOI：10.1016/j.tetlet.2003.08.089

  日期：2003.10

  Alkylation of lactam 10, first with iodide 15 and then with MeI, gave mainly (18:1) lactam 18. This was converted by treatment with t-BuLi and then with aqueous base into enone 4, which was elaborated into (-)-hamigeran B. A key feature of the last part of the synthesis is the use of t-BuMe2Si-groups (as in intermediate 24) both to direct hydrogenation from the appropriate face and to protect the benzylic C-O bond from hydrogenolysis. (C) 2003 Elsevier Ltd. All rights reserved.
• Clive, Derrick L J; Wang, Jian, Journal of Organic Chemistry, 2004, vol. 69, # 8, p. 2773 - 2784
  作者：Clive, Derrick L J、Wang, Jian

  DOI：——

  日期：——