(2Z,4Z)-8,11,14,17-tetraoxa-cycloheptadeca-2,4-diene-1,6-dione | 251961-52-1

• 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: (2Z,4Z)-8,11,14,17-tetraoxa-cycloheptadeca-2,4-diene-1,6-dione
• 英文别名: (12Z,14Z)-1,4,7,10-tetraoxacycloheptadeca-12,14-diene-11,16-dione
• CAS: 251961-52-1
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: NLHSRISKHCTXSO-CCAGOZQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2Z,4Z)-8,11,14,17-tetraoxa-cycloheptadeca-2,4-diene-1,6-dione 在 碘 作用下， 以 氘代氯仿 为溶剂， 反应 0.33h， 以100%的产率得到(2Z,4E)-8,11,14,17-tetraoxa-cycloheptadeca-2,4-diene-1,6-dione
  参考文献：
  名称：

  Catalytic Intramolecular Addition of Metal Carbenes to Remote Furans

  摘要：

  [GRAPHICS]Diazo esters and diazo ketones linked to a furan undergo catalytic intramolecular addition of an intermediate metal carbene to the remote furan to form diendiones with ring sizes up to 17. Regioselectivity is catalyst dependent with addition to either the more or less substituted double bond. The high product yields and absence of need for high dilution suggest that this methodology is general for macrocycle preparations.

  DOI：

  10.1021/ol990168t
• 作为产物：
  描述：

  8-(furfuryloxy)-3,6-dioxa-1-octyl diazoacetate 在 rhodium(II) acetate dimer 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到(2E,4Z)-8,11,14,17-tetraoxa-cycloheptadeca-2,4-diene-1,6-dione
  参考文献：
  名称：

  Catalytic Intramolecular Addition of Metal Carbenes to Remote Furans

  摘要：

  [GRAPHICS]Diazo esters and diazo ketones linked to a furan undergo catalytic intramolecular addition of an intermediate metal carbene to the remote furan to form diendiones with ring sizes up to 17. Regioselectivity is catalyst dependent with addition to either the more or less substituted double bond. The high product yields and absence of need for high dilution suggest that this methodology is general for macrocycle preparations.

  DOI：

  10.1021/ol990168t

文献信息

• Reactivities and selectivities in macrocyclic addition reactions with diazoacetates using copper(I) and rhodium(II) catalysts
  作者：Michael P. Doyle、Wenhao Hu

  DOI：10.1016/s0040-4039(00)01075-3

  日期：2000.8

  Reactions of diazoacetates linked through three ethylene glycol units to allyl, methallyl, propargyl, or furfuryl, catalyzed by copper(I) and rhodium(II) compounds, are investigated for chemoselectivity, diastereoselectivity, and enantioselectivity. The most reactive catalysts show the highest preference for addition over carbon–hydrogen insertion. Addition is favored in the order: prapargyl>furfuyl>methallyl

  研究了通过三个乙二醇单元连接的重氮乙酸酯与烯丙基，甲基烯丙基，炔丙基或糠基的反应，该反应由铜（I）和铑（II）化合物催化，具有化学选择性，非对映选择性和对映选择性。与碳氢插入相比，反应性最高的催化剂显示出最高的添加偏好。按顺序优选加料：prapargyl>糠基>甲基烯丙基，烯丙基。