1,2-Dihydro-5-methoxybenzocyclobuten-1-ol | 55171-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-Dihydro-5-methoxybenzocyclobuten-1-ol
• 英文别名: 4-Methoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-ol；4-methoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-ol
• CAS: 55171-79-4
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: ZBAYUHVPFCTOSP-UHFFFAOYSA-N

物化性质

• 沸点：
  282.7±40.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1,2-Dihydro-5-methoxybenzocyclobuten-1-ol 、 富马酸二乙酯 在 溴丁基-镁 、 L-(+)-酒石酸二异丙酯 、 二异丙基锌 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 96.5h， 生成 、 diethyl (1S,2S,3R)-1-hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate 、 diethyl (1S,2R,3S)-1-hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate 、 diethyl (1R,2R,3S)-1-hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate
  参考文献：
  名称：

  Enantioselective Diels–Alder reaction of o-quinodimethanes by utilizing tartaric acid ester as a chiral auxiliary

  摘要：

  The asymmetric Diels-Alder reaction of o-quinodimethanes, generated from benzocyclobutenols in situ, with fumaric acid esters was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active 1,2-cis-substituted 1-hydroxy tetrahydronaphthalene derivatives with enantioselectivities up to 83% ee. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.05.025

文献信息

• Enantioselective Diels–Alder reaction of o-quinodimethanes by utilizing tartaric acid ester as a chiral auxiliary
  作者：Motoki Takinami、Yutaka Ukaji、Katsuhiko Inomata

  DOI：10.1016/j.tetasy.2006.05.025

  日期：2006.6

  The asymmetric Diels-Alder reaction of o-quinodimethanes, generated from benzocyclobutenols in situ, with fumaric acid esters was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active 1,2-cis-substituted 1-hydroxy tetrahydronaphthalene derivatives with enantioselectivities up to 83% ee. (c) 2006 Elsevier Ltd. All rights reserved.