carbonic acid 2-bromo-4-heptyl-3-hydroxy-phenyl ester tert-butyl ester | 680997-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: carbonic acid 2-bromo-4-heptyl-3-hydroxy-phenyl ester tert-butyl ester
• CAS: 680997-61-9
• 化学式: C₁₈H₂₇BrO₄
• 分子量: 387.314
• InChiKey: OAJFZDAJIZEDGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  carbonic acid 2-bromo-4-heptyl-3-hydroxy-phenyl ester tert-butyl ester 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 [双(三氟乙酰氧基)碘]苯 、 zinc dibromide 作用下， 以 乙醚 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 4.33h， 生成 5-bromo-8a-heptyl-3-methyl-8aH-benzo[1,4]dioxine-2,6-dione
  参考文献：
  名称：

  Diastereoselective Dearomatization of Resorcinols Directed by a Lactic Acid Tether:  Unprecedented Enantioselective Access to p-Quinols

  摘要：

  An operationally simple oxidative dearomatization of resorcinol derivatives is reported that employs an inexpensive chiral directing group. The method provides access to a variety of p-quinol derivatives in good yield and diastereoselectivity. A short reductive process affords 4-hydroxy-4-alkylcyclohexenone derivatives in excellent yields and enantiomeric excesses.

  DOI：

  10.1021/ol0498592
• 作为产物：
  描述：

  3-bromo-2,4-dihydroxybenzaldehyde 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.17h， 生成 carbonic acid 2-bromo-4-heptyl-3-hydroxy-phenyl ester tert-butyl ester
  参考文献：
  名称：

  Diastereoselective Dearomatization of Resorcinols Directed by a Lactic Acid Tether:  Unprecedented Enantioselective Access to p-Quinols

  摘要：

  An operationally simple oxidative dearomatization of resorcinol derivatives is reported that employs an inexpensive chiral directing group. The method provides access to a variety of p-quinol derivatives in good yield and diastereoselectivity. A short reductive process affords 4-hydroxy-4-alkylcyclohexenone derivatives in excellent yields and enantiomeric excesses.

  DOI：

  10.1021/ol0498592

文献信息

• Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones
  作者：Todd A. Wenderski、Christophe Hoarau、Lupe Mejorado、Thomas R.R. Pettus

  DOI：10.1016/j.tet.2010.05.041

  日期：2010.7

  The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized chiral six and seven-membered ring systems. Herein, we report a multitude of remarkable and unexpected diastereoselective transformations stemming from these cyclohexadienone adducts. Published by Elsevier Ltd.