methyl 3-(1-ethylcyclopropyl)methoxy-5-methylbenzoate | 1194258-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-(1-ethylcyclopropyl)methoxy-5-methylbenzoate
• 英文别名: DY-4-101；Methyl 3-[(1-ethylcyclopropyl)methoxy]-5-methylbenzoate
• CAS: 1194258-30-4
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: ICYZYZDMRULSBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(1-ethylcyclopropyl)methoxy-5-methylbenzoate 、 特戊酸碘甲酯 在 氨 、 lithium 作用下， 以 叔丁醇 、 反-1,3-戊二烯 为溶剂， 反应 3.0h， 生成 methyl 3-((1-ethylcyclopropyl)methoxy)-5-methyl-1-((pivaloyloxy)methyl)cyclohexa-2,5-diene-1-carboxylate
  参考文献：
  名称：

  Two Approaches to Diverting the Course of a Free-Radical Cyclization: Application of Cyclopropylcarbinyl Radical Fragmentations and Allenes as Radical Acceptors

  摘要：

  Free radical cyclization of 4 and 7 gave the expected cyclization-reduction products (5 and 8) along with considerable amounts of products derived from a cyclization-atom transfer-secondary cyclization process (6 and 9). Two approaches to avoiding these unexpected products were explored. Use of a cyclopropylcarbinyl fragmentation avoided the secondary cyclization reaction (25 or 43 -> 26 or 44), whereas use of an allene as a radical acceptor avoided the atom-transfer reaction altogether (49 -> 52).

  DOI：

  10.1021/jo901834q
• 作为产物：
  描述：

  (1-ethylcyclopropyl)methanol 、 3-羟基-5-碘苯甲酸甲酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以57%的产率得到methyl 3-(1-ethylcyclopropyl)methoxy-5-methylbenzoate
  参考文献：
  名称：

  Two Approaches to Diverting the Course of a Free-Radical Cyclization: Application of Cyclopropylcarbinyl Radical Fragmentations and Allenes as Radical Acceptors

  摘要：

  Free radical cyclization of 4 and 7 gave the expected cyclization-reduction products (5 and 8) along with considerable amounts of products derived from a cyclization-atom transfer-secondary cyclization process (6 and 9). Two approaches to avoiding these unexpected products were explored. Use of a cyclopropylcarbinyl fragmentation avoided the secondary cyclization reaction (25 or 43 -> 26 or 44), whereas use of an allene as a radical acceptor avoided the atom-transfer reaction altogether (49 -> 52).

  DOI：

  10.1021/jo901834q

文献信息

• Two Approaches to Diverting the Course of a Free-Radical Cyclization: Application of Cyclopropylcarbinyl Radical Fragmentations and Allenes as Radical Acceptors
  作者：Dexi Yang、Valerie Cwynar、Matthew G. Donahue、David J. Hart、Grace Mbogo

  DOI：10.1021/jo901834q

  日期：2009.11.20

  Free radical cyclization of 4 and 7 gave the expected cyclization-reduction products (5 and 8) along with considerable amounts of products derived from a cyclization-atom transfer-secondary cyclization process (6 and 9). Two approaches to avoiding these unexpected products were explored. Use of a cyclopropylcarbinyl fragmentation avoided the secondary cyclization reaction (25 or 43 -> 26 or 44), whereas use of an allene as a radical acceptor avoided the atom-transfer reaction altogether (49 -> 52).