Acetic acid 3-bromo-4-tert-butoxy-phenyl ester | 854937-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: Acetic acid 3-bromo-4-tert-butoxy-phenyl ester
• CAS: 854937-69-2
• 化学式: C₁₂H₁₅BrO₃
• 分子量: 287.153
• InChiKey: WPVVWDWKHMSVBU-UHFFFAOYSA-N

物化性质

• 沸点：
  331.2±32.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Acetic acid 3-bromo-4-tert-butoxy-phenyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以99%的产率得到3-Bromo-4-(tert-butoxy)phenol
  参考文献：
  名称：

  Avoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3′-disubstituted derivatives

  摘要：

  The Ullmann coupling of 1 (R = H) gives a 2:1 mixture of diastereomers 2 (R = H) in 81% yield that are easily separated by silica gel chromatography. This procedure avoids the generally cumbersome and sometimes difficult resolution step with DBTA. Similar Ullmann couplings and separation of the corresponding diastereomers are employed with other derivatives of I (R = OtBu, iPr, Ph, and mesityl) ultimately affording a new series of 3,3'-disubsituted-MeO-BIPHEP derivatives. The use of these new derivatives in palladium-catalyzed asymmetric Heck reaction, Pd-catalyzed polyene cyclizations and rhodium-catalyzed hydrogenations is also reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.183
• 作为产物：
  描述：

  对苯二酚 在 三氟甲磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Acetic acid 3-bromo-4-tert-butoxy-phenyl ester
  参考文献：
  名称：

  Avoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3′-disubstituted derivatives

  摘要：

  The Ullmann coupling of 1 (R = H) gives a 2:1 mixture of diastereomers 2 (R = H) in 81% yield that are easily separated by silica gel chromatography. This procedure avoids the generally cumbersome and sometimes difficult resolution step with DBTA. Similar Ullmann couplings and separation of the corresponding diastereomers are employed with other derivatives of I (R = OtBu, iPr, Ph, and mesityl) ultimately affording a new series of 3,3'-disubsituted-MeO-BIPHEP derivatives. The use of these new derivatives in palladium-catalyzed asymmetric Heck reaction, Pd-catalyzed polyene cyclizations and rhodium-catalyzed hydrogenations is also reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.183