2-[2-[2-(2-Diazoacetyl)oxyethoxy]ethoxy]ethyl 2-diazoacetate | 700865-77-6

• 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-Diazoacetyl)oxyethoxy]ethoxy]ethyl 2-diazoacetate
• 英文别名: 2-[2-[2-(2-diazoacetyl)oxyethoxy]ethoxy]ethyl 2-diazoacetate
• CAS: 700865-77-6
• 化学式: C₁₀H₁₄N₄O₆
• 分子量: 286.244
• InChiKey: VGUHGCWWDFJDPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[2-[2-(2-Diazoacetyl)oxyethoxy]ethoxy]ethyl 2-diazoacetate 在 chloro[(2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)di-tert-butylphosphine]gold(I) 、 四(3,5-二(三氟甲基)苯基)硼酸钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以62%的产率得到(12Z)-1,4,7,10-tetraoxacyclotetradec-12-ene-11,14-dione
  参考文献：
  名称：

  Gold-catalyzed intramolecular diazo coupling: an efficient macrocyclization towards cyclic olefins

  摘要：

  一种利用金催化的合成中等到大环烯烃的方法已经开发出来了。

  DOI：

  10.1039/c5cc04830c
• 作为产物：
  描述：

  3,6-dioxaocta-1,8-diyl bis(3-oxobutanoate) 在 对甲苯磺酰叠氮 、 三乙胺 、 lithium hydroxide 作用下， 以 乙腈 、 水 为溶剂， 反应 10.0h， 以83%的产率得到2-[2-[2-(2-Diazoacetyl)oxyethoxy]ethoxy]ethyl 2-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

• 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.
• Gold-catalyzed intramolecular diazo coupling: an efficient macrocyclization towards cyclic olefins
  作者：Chenghao Zhu、Guangyang Xu、Kai Liu、Lin Qiu、Shiyong Peng、Jiangtao Sun

  DOI：10.1039/c5cc04830c

  日期：——

  A gold-catalyzed synthesis of medium to large membered cyclic olefins has been developed.

  一种利用金催化的合成中等到大环烯烃的方法已经开发出来了。