methyl 2-bromo-2-(1-hydroxycyclopent-2-enyl)cyclopropanecarboxylate | 269060-35-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-bromo-2-(1-hydroxycyclopent-2-enyl)cyclopropanecarboxylate
• 英文别名: methyl 2-bromo-2-(1-hydroxycyclopent-2-en-1-yl)cyclopropane-1-carboxylate
• CAS: 269060-35-7
• 化学式: C₁₀H₁₃BrO₃
• 分子量: 261.115
• InChiKey: HDSJUHRRMJMEAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-bromo-2-(1-hydroxycyclopent-2-enyl)cyclopropanecarboxylate 在 aluminum oxide 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 methyl 7,8-dihydrocalicene-7-carboxylate
  参考文献：
  名称：

  摘要：

  Cyclopent-2-en-1-one is a versatile electrophilic cyclopentadiene equivalent in reactions with 1-bromo-1-lithiocyclopropanes. The synthetic sequence (outlined in Scheme 1) has been applied to the synthesis of functionalized 7-X-7,8-dihydrocalicenes 13c (Scheme 3) and 13d (Scheme 4). 7-Bromo-7,8-dihydrocalicene (13d) is considered to be a promising precursor of the so far unknown parent calicene (2). A similar sequence has been realized for 7-(chloromethyl)-7,8-dihydrocalicene (21a, Scheme 5) which, under appropriate conditions, could give 7-methylcalicene (16).

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<571::aid-hlca571>3.0.co;2-m
• 作为产物：
  描述：

  2-环戊烯酮 、 methyl 2,2-dibromocyclopropanecarboxylate 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 以32%的产率得到methyl 2-bromo-2-(1-hydroxycyclopent-2-enyl)cyclopropanecarboxylate
  参考文献：
  名称：

  摘要：

  Cyclopent-2-en-1-one is a versatile electrophilic cyclopentadiene equivalent in reactions with 1-bromo-1-lithiocyclopropanes. The synthetic sequence (outlined in Scheme 1) has been applied to the synthesis of functionalized 7-X-7,8-dihydrocalicenes 13c (Scheme 3) and 13d (Scheme 4). 7-Bromo-7,8-dihydrocalicene (13d) is considered to be a promising precursor of the so far unknown parent calicene (2). A similar sequence has been realized for 7-(chloromethyl)-7,8-dihydrocalicene (21a, Scheme 5) which, under appropriate conditions, could give 7-methylcalicene (16).

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<571::aid-hlca571>3.0.co;2-m

文献信息

• ——
  作者：Ahmad Al-Dulayymi、Xiaoming Li、Markus Neuenschwander

  DOI：10.1002/(sici)1522-2675(20000315)83:3<571::aid-hlca571>3.0.co;2-m

  日期：2000.3.15

  Cyclopent-2-en-1-one is a versatile electrophilic cyclopentadiene equivalent in reactions with 1-bromo-1-lithiocyclopropanes. The synthetic sequence (outlined in Scheme 1) has been applied to the synthesis of functionalized 7-X-7,8-dihydrocalicenes 13c (Scheme 3) and 13d (Scheme 4). 7-Bromo-7,8-dihydrocalicene (13d) is considered to be a promising precursor of the so far unknown parent calicene (2). A similar sequence has been realized for 7-(chloromethyl)-7,8-dihydrocalicene (21a, Scheme 5) which, under appropriate conditions, could give 7-methylcalicene (16).