3-(乙氧甲酰)-3-(甲基乙氧甲酰)-5-(1H,1H-全氟壬基)-丁内酯 | 674786-75-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-(乙氧甲酰)-3-(甲基乙氧甲酰)-5-(1H,1H-全氟壬基)-丁内酯
• 英文名称: cis/trans-4-(perfluorooctyl)methyl-2-carboethoxymethyl-2-carboethoxy-4-hydroxy-butanoic acid γ-lactone
• 英文别名: Ethyl 3-(2-ethoxy-2-oxoethyl)-5-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl)-2-oxooxolane-3-carboxylate
• CAS: 674786-75-5
• 化学式: C₂₀H₁₇F₁₇O₆
• 分子量: 676.324
• InChiKey: ZXPKQENNVJKVQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  23

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-(乙氧甲酰)-3-(甲基乙氧甲酰)-5-(1H,1H-全氟壬基)-丁内酯 在 氢氧化钾 作用下， 反应 7.0h， 生成 2-carboxymethyl-2-carboxy-4-hydroxy-4-(perfluorooctyl)methyl-butanoic acid γ-lactone 、 2-carboxymethyl-2-carboxy-4-hydroxy-4-(perfluorooctyl)methyl-butanoic acid γ-lactone
  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 sodium 、 过氧化苯甲酰 作用下， 以 乙醇 为溶剂， 反应 4.5h， 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

文献信息

• Radical addition of RFI to alkenylsuccinic anhydrides and gem-substituted alkenyl triesters
  作者：Neal O Brace

  DOI：10.1016/s0022-1139(03)00160-x

  日期：2003.10

  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.