1,4,7,10,13,16,19-heptaoxacyclotricos-21-ene-20,23-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 1,4,7,10,13,16,19-heptaoxacyclotricos-21-ene-20,23-dione
• 英文别名: (21Z)-1,4,7,10,13,16,19-heptaoxacyclotricos-21-ene-20,23-dione
• 化学式: C₁₆H₂₆O₉
• 分子量: 362.377
• InChiKey: QILVJJVQXXJJAY-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  六甘醇 在 [Ru(2,6-Cl2tpp)CO] 对甲苯磺酰叠氮 、 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 33.0h， 生成 1,4,7,10,13,16,19-heptaoxacyclotricos-21-ene-20,23-dione
  参考文献：
  名称：

  Highly Selective Intra- and Intermolecular Coupling Reactions of Diazo Compounds to Form cis-Alkenes Using a Ruthenium Porphyrin Catalyst

  摘要：

  [Ru(2,6-Cl2TPP)(CO)] catalyzed intramolecular coupling reactions of bisdiazoacetates and intermolecular coupling reactions of monodiazoacetates to afford the coupling products in up to 76% and 93% yields, respectively. Only the cis isomers were obtained from the reactions. Employing such a ruthenium-catalyzed coupling reaction of a diazo compound as a key step allowed the synthesis of Patulolide B in 67% yield with a ratio of >40:1 against its trans isomer.

  DOI：

  10.1021/ol049626a

文献信息

• A New Approach to Macrocyclization via Alkene Formation in Catalytic Diazo Decomposition. Synthesis of Patulolides A and B
  作者：Michael P. Doyle、Wenhao Hu、Iain M. Phillips、Andrew G. H. Wee

  DOI：10.1021/ol005983j

  日期：2000.6.1

  [GRAPHICS]Effective synthetic uses of bisdiazocarbonyl compounds for the selective construction of diverse macrocycles, including the synthesis of patulolides A and a, by catalytic "carbene dimer" formation are reported. Control of stereochemistry and efficient methods for product isomerization or kinetic isomer differentiation have been achieved.
• Highly Selective Intra- and Intermolecular Coupling Reactions of Diazo Compounds to Form <i>cis</i>-Alkenes Using a Ruthenium Porphyrin Catalyst
  作者：Gong-Yong Li、Chi-Ming Che

  DOI：10.1021/ol049626a

  日期：2004.5.1

  [Ru(2,6-Cl2TPP)(CO)] catalyzed intramolecular coupling reactions of bisdiazoacetates and intermolecular coupling reactions of monodiazoacetates to afford the coupling products in up to 76% and 93% yields, respectively. Only the cis isomers were obtained from the reactions. Employing such a ruthenium-catalyzed coupling reaction of a diazo compound as a key step allowed the synthesis of Patulolide B in 67% yield with a ratio of >40:1 against its trans isomer.