ethyl [5-iodo-6-(perfluorooctyl)-3,3-bis-carboethoxy]hexanoate | 674786-73-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl [5-iodo-6-(perfluorooctyl)-3,3-bis-carboethoxy]hexanoate
• CAS: 674786-73-3
• 化学式: C₂₂H₂₂F₁₇IO₆
• 分子量: 832.29
• InChiKey: XLYGLQPVGKHQIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  466.9±45.0 °C(Predicted)
• 密度：
  1.618±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.65
• 重原子数：
  46.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl [5-iodo-6-(perfluorooctyl)-3,3-bis-carboethoxy]hexanoate 142.0 ℃ 、6.67 Pa 条件下， 生成 3-(乙氧甲酰)-3-(甲基乙氧甲酰)-5-(1H,1H-全氟壬基)-丁内酯
  参考文献：
  名称：

  Radical addition of RFI to alkenylsuccinic anhydrides and gem-substituted alkenyl triesters

  摘要：

  Radical addition of RFI to alkenylsuccinic anhydrides affords omega-(perfluoroalkyl)-delta-iodoalkyl-2-butane-1,4-dioc acid anhydrides, and these adducts are reductively dehalogenated and esterified by zinc and acid in ethanol without lactonization. However, the RFI adducts react with KOH in ethanol to give the alkenyl half esters (but no gamma-lactone), which convert to the gamma-lactones by acid catalysis. When treated with water, ethanol, Zn and 48% HBr, the RFI adduct from but-3-en-2-yl-succinic anhydride converts to the iodo half ester, RFCH2CHICH(CH3)CH(CO2H)CH2CO2Et, which undergoes Zn induced (S(H)i) conversion to gamma-lactone. RFI (AIBN) and the triester CH2=CHCH2C(CO2Et)(2)CH2CO2Et yield RFCH2CHICH2C(CO2Et)(2)CH2CO2Et (95%). When heated to 140 degreesC, the adduct loses iodoethane and cyclizes to diester gamma-lactones (94%). With benzoyl peroxide, RFI and the triester at 99 degreesC, spontaneous radical cyclization of the adduct to lactone occurs. Evidently, the gem-disubstituted triester readily forms a five-membered lactone as a consequence of steric compression in the open chain form. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00160-x
• 作为产物：
  描述：

  1,1,2-乙烷三羧酸三乙酯 在 偶氮二异丁腈 、 sodium 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 ethyl [5-iodo-6-(perfluorooctyl)-3,3-bis-carboethoxy]hexanoate
  参考文献：
  名称：

  Radical addition of RFI to alkenylsuccinic anhydrides and gem-substituted alkenyl triesters

  摘要：

  Radical addition of RFI to alkenylsuccinic anhydrides affords omega-(perfluoroalkyl)-delta-iodoalkyl-2-butane-1,4-dioc acid anhydrides, and these adducts are reductively dehalogenated and esterified by zinc and acid in ethanol without lactonization. However, the RFI adducts react with KOH in ethanol to give the alkenyl half esters (but no gamma-lactone), which convert to the gamma-lactones by acid catalysis. When treated with water, ethanol, Zn and 48% HBr, the RFI adduct from but-3-en-2-yl-succinic anhydride converts to the iodo half ester, RFCH2CHICH(CH3)CH(CO2H)CH2CO2Et, which undergoes Zn induced (S(H)i) conversion to gamma-lactone. RFI (AIBN) and the triester CH2=CHCH2C(CO2Et)(2)CH2CO2Et yield RFCH2CHICH2C(CO2Et)(2)CH2CO2Et (95%). When heated to 140 degreesC, the adduct loses iodoethane and cyclizes to diester gamma-lactones (94%). With benzoyl peroxide, RFI and the triester at 99 degreesC, spontaneous radical cyclization of the adduct to lactone occurs. Evidently, the gem-disubstituted triester readily forms a five-membered lactone as a consequence of steric compression in the open chain form. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00160-x