1-(2-hydroxyphenyl)heptane-1,6-dione | 1237740-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxyphenyl)heptane-1,6-dione
• 英文别名: 1-(2-Hydroxyphenyl)-1,6-heptanedione
• CAS: 1237740-92-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: ORDUKSMMXGXPBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)heptane-1,6-dione 在 四氢吡咯 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以87%的产率得到1,2,3,3a-tetrahydro-3a-methylcyclopenta[b]chromen-9(9aH)-one
  参考文献：
  名称：

  Synthesis of Substituted Chromanones: An Organocatalytic Aldol/oxa-Michael Reaction

  摘要：

  A diastereoselective organocatalytic aldol/oxa-Michael reaction has been developed to efficiently deliver medicinally relevant 2,3-ring-substituted chromanones. Development of this synthetic strategy revealed an unexpected kinetic anti-Saytzeff elimination; an origin for the observed selectivity is suggested on the basis of the results of quantum chemical calculations. This unusual kinetic selectivity necessitated an isomerization protocol that in turn led to the discovery of an intriguing Pd-mediated isomerization/intramolecular Friedel-Crafts-type alkylation.

  DOI：

  10.1021/ol101221c
• 作为产物：
  描述：

  2-(2-methylcyclohex-1-enyl)phenol 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以89%的产率得到1-(2-hydroxyphenyl)heptane-1,6-dione
  参考文献：
  名称：

  Synthesis of Substituted Chromanones: An Organocatalytic Aldol/oxa-Michael Reaction

  摘要：

  A diastereoselective organocatalytic aldol/oxa-Michael reaction has been developed to efficiently deliver medicinally relevant 2,3-ring-substituted chromanones. Development of this synthetic strategy revealed an unexpected kinetic anti-Saytzeff elimination; an origin for the observed selectivity is suggested on the basis of the results of quantum chemical calculations. This unusual kinetic selectivity necessitated an isomerization protocol that in turn led to the discovery of an intriguing Pd-mediated isomerization/intramolecular Friedel-Crafts-type alkylation.

  DOI：

  10.1021/ol101221c

文献信息

• Synthesis of Substituted Chromanones: An Organocatalytic Aldol/oxa-Michael Reaction
  作者：Jeffrey D. Butler、Wayne E. Conrad、Michael W. Lodewyk、James C. Fettinger、Dean J. Tantillo、Mark J. Kurth

  DOI：10.1021/ol101221c

  日期：2010.8.6

  A diastereoselective organocatalytic aldol/oxa-Michael reaction has been developed to efficiently deliver medicinally relevant 2,3-ring-substituted chromanones. Development of this synthetic strategy revealed an unexpected kinetic anti-Saytzeff elimination; an origin for the observed selectivity is suggested on the basis of the results of quantum chemical calculations. This unusual kinetic selectivity necessitated an isomerization protocol that in turn led to the discovery of an intriguing Pd-mediated isomerization/intramolecular Friedel-Crafts-type alkylation.