dimethyl 2,15-difluoro-3,3,14,14-tetramethylhexadecanedioate | 122332-96-1

• 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: dimethyl 2,15-difluoro-3,3,14,14-tetramethylhexadecanedioate
• CAS: 122332-96-1
• 化学式: C₂₂H₄₀F₂O₄
• 分子量: 406.554
• InChiKey: NTKWYIDLDKMUHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  28.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2,15-difluoro-3,3,14,14-tetramethylhexadecanedioate 在 四丁基氟化铵 作用下， 反应 16.0h， 以38%的产率得到2,15-difluoro-3,3,14,14-tetramethylhexadecanedioic acid
  参考文献：
  名称：

  Synthesis and hypolipidemic and antidiabetogenic activities of .beta.,.beta.,.beta.',.beta.'-tetrasubstituted, long-chain dioic acids

  摘要：

  beta,beta,beta',beta'-Tetrasubstituted, long-chain dioic acids of the general formula HOOC-C(XY)-C(R2)-Q-C-(R2)-C(XY)-COOH have been synthesized and evaluated as hypotriglyceridemic-hypocholesterolemic agents in rats and as antidiabetogenic agents in ob/ob diabetic mice. The free carboxyl function of analogues of the series was mandatory for their hypolipidemic-antidiabetogenic effect while nonhydrolyzable diesters were inactive. Other structure-activity relationships were determined as a function of the overall chain length (C12-C22), alpha,alpha'-substitutions (X, Y = H, F, Cl, Br, OH, CN), beta, beta'-substitutions (R = CH3, C6H5), and core substitutions [Q = (CH2)10, (CH2)4CH = CH(CH2)4, 1,4-C6H10[(CH2)3]2, 1,4-C6H4[(CH2)3]2, 1,4-C6H4(CH = CHCH2)2, CH2(OCH2CH2)3OCH2)]. The most effective hypolipidemic-antidiabetogenic members of the series were alpha,alpha'-nonsubstituted, beta,beta'-methyl-substituted analogues of 14-18-carbon chains having either a saturated aliphatic core or a 1,4-bis(propenyl)benzene core in the cis/trans configuration. The hypotriglyceridemic rather than the hypocholesterolemic capacity of members of the series was found to correlate with their respective capacities as liver peroxisomal proliferators in rats.

  DOI：

  10.1021/jm00129a010
• 作为产物：
  描述：

  3,3,14,14-tetramethyl-1,16-hexadecanedioic acid chloride 在 甲醇 、 硫酸 、 四丁基氟化铵 、 溴 作用下， 以 四氯化碳 为溶剂， 反应 40.0h， 生成 dimethyl 2,15-difluoro-3,3,14,14-tetramethylhexadecanedioate
  参考文献：
  名称：

  Synthesis and hypolipidemic and antidiabetogenic activities of .beta.,.beta.,.beta.',.beta.'-tetrasubstituted, long-chain dioic acids

  摘要：

  beta,beta,beta',beta'-Tetrasubstituted, long-chain dioic acids of the general formula HOOC-C(XY)-C(R2)-Q-C-(R2)-C(XY)-COOH have been synthesized and evaluated as hypotriglyceridemic-hypocholesterolemic agents in rats and as antidiabetogenic agents in ob/ob diabetic mice. The free carboxyl function of analogues of the series was mandatory for their hypolipidemic-antidiabetogenic effect while nonhydrolyzable diesters were inactive. Other structure-activity relationships were determined as a function of the overall chain length (C12-C22), alpha,alpha'-substitutions (X, Y = H, F, Cl, Br, OH, CN), beta, beta'-substitutions (R = CH3, C6H5), and core substitutions [Q = (CH2)10, (CH2)4CH = CH(CH2)4, 1,4-C6H10[(CH2)3]2, 1,4-C6H4[(CH2)3]2, 1,4-C6H4(CH = CHCH2)2, CH2(OCH2CH2)3OCH2)]. The most effective hypolipidemic-antidiabetogenic members of the series were alpha,alpha'-nonsubstituted, beta,beta'-methyl-substituted analogues of 14-18-carbon chains having either a saturated aliphatic core or a 1,4-bis(propenyl)benzene core in the cis/trans configuration. The hypotriglyceridemic rather than the hypocholesterolemic capacity of members of the series was found to correlate with their respective capacities as liver peroxisomal proliferators in rats.

  DOI：

  10.1021/jm00129a010

文献信息

• BAR-TANA, JACOB;BEN-SHOSHAN, SHOSHANA;BLUM, JOCHANAN;MIGRON, YOELIT;HERTZ+, J. MED. CHEM., 32,(1989) N, C. 2072-2084
  作者：BAR-TANA, JACOB、BEN-SHOSHAN, SHOSHANA、BLUM, JOCHANAN、MIGRON, YOELIT、HERTZ+

  DOI：——

  日期：——