2-{2-[2-(2-{2-[2-(2-diazoacetoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}ethyl diazoacetate | 282532-09-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-{2-[2-(2-{2-[2-(2-diazoacetoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}ethyl diazoacetate
• 英文别名: 2-[2-[2-[2-[2-[2-(2-Diazoacetyl)oxyethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 2-diazoacetate；2-[2-[2-[2-[2-[2-(2-diazoacetyl)oxyethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 2-diazoacetate
• CAS: 282532-09-6
• 化学式: C₁₆H₂₆N₄O₉
• 分子量: 418.404
• InChiKey: YSERFCNKUZUPIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  29
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-{2-[2-(2-{2-[2-(2-diazoacetoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}ethyl diazoacetate 在 [Ru(2,6-Cl2tpp)CO] 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 21.0h， 以65%的产率得到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
• 作为产物：
  描述：

  六甘醇 在 对甲苯磺酰叠氮 、 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 生成 2-{2-[2-(2-{2-[2-(2-diazoacetoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}ethyl diazoacetate
  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.