3,3,14,14-tetramethyl-1,16-hexadecanedioic acid chloride | 87272-31-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 3,3,14,14-tetramethyl-1,16-hexadecanedioic acid chloride
• 英文别名: 3,3,14,14-tetramethylhexadecanedioyl dichloride
• CAS: 87272-31-9
• 化学式: C₂₀H₃₆Cl₂O₂
• 分子量: 379.411
• InChiKey: QAUPJBVGLNCXIV-UHFFFAOYSA-N

物化性质

• 沸点：
  430.9±18.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  24.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3,3,14,14-四甲基十六烷二酸 在 氯化亚砜 作用下， 反应 1.0h， 生成 3,3,14,14-tetramethyl-1,16-hexadecanedioic acid chloride
  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

• A facile synthesis of α,α,ω,ω-tetrahalo-α,ω-dicarboxylic esters
  作者：Yoelit Migron、Jochanan Blum、Jacob Bar-Tana

  DOI：10.1016/s0040-4020(01)89964-6

  日期：1987.1

  synthesis of some α,α,ω,ω-tetrachloro and tetrabromo-derivatives of the hypolipidemic 3,3,14,14-tetramethylhexadecanedioic acid from α,ω-dihalo-esters, carbon tetrahalides and lithium diisopropyl amide has been described. Interaction of α,ω-dichloro esters with CBr4 was shown to give the expected α,ω-dibromo-α,ω-dichloro compounds, but treatment of bis(l-methylethyl) 2,15-dibromo-3,3,14,14-tetramethyl

  已经描述了由α，ω-二卤代酯，四卤化碳和二异丙基氨基锂合成一些降血脂性3，3，14，14-四甲基十六烷二酸的α，α，ω，ω-四氯和四溴衍生物。研究表明，α，ω-二氯酯与CBr 4的相互作用产生了预期的α，ω-二溴-α，ω-二氯化合物，但处理了双（1-甲基乙基）2,15-dibromo-3,3,14发现具有CCl 4的14，4-四甲基六癸二酸酯导致卤素交换，产生四氯二酯作为主要产物。
• WO2008/18877
  申请人：——

  公开号：——

  公开（公告）日：——
• 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：——