2,15-dibromo-3,3,14,14-tetramethyl hexadecane-1,16-dioyl chloride | 87272-25-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 2,15-dibromo-3,3,14,14-tetramethyl hexadecane-1,16-dioyl chloride
• 英文别名: 2,15-Dibromo-3,3,14,14-tetramethylhexadecanedioyl dichloride
• CAS: 87272-25-1
• 化学式: C₂₀H₃₄Br₂Cl₂O₂
• 分子量: 537.203
• InChiKey: KPHPVCBJEYOVIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,15-dibromo-3,3,14,14-tetramethyl hexadecane-1,16-dioyl chloride 在 水 作用下， 反应 20.0h， 以60%的产率得到2,15-dibromo-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 溴 作用下， 以 四氯化碳 为溶剂， 反应 20.0h， 以84%的产率得到2,15-dibromo-3,3,14,14-tetramethyl hexadecane-1,16-dioyl 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

• Long-chain .alpha.,.omega.-dicarboxylic acids and derivatives thereof
  申请人：Epis S.A.

  公开号：US04689344A1

  公开（公告）日：1987-08-25

  A novel class of compounds has been found to be effective in blocking cholesterol and neutral lipid synthesis in-vivo without adversely affecting energy metabolism, useful for the treatment of obesity, hyperlipidemia and maturity-onset diabetes. The active compounds have the general formula ##STR1## or in-vivo hydrolyzable functional derivatives of the carboxylic groups thereof, wherein R.sub.1 and R.sub.2 each independently represents an unsubstituted or substituted hydrocarbyl or hetercyclyl radical; X and Y each independently represents hydrogen, optionally substituted lower alkyl, halogen, cyano, carboxy, lower alkoxycarbonyl or carbamoyl; and Q represents a diradical consisting of a linear chain of 8 to 14 carbon atoms, one or more of which may be replaced by heteroatoms, said chain being optionally substituted by inert substituents and one or more of said carbon or heteratom chain members optionally forming part of a ring structure.

  一种新的化合物类别已经发现在体内有效地阻断胆固醇和中性脂质合成，而不会对能量代谢产生不良影响，对于治疗肥胖、高脂血症和成人发病型糖尿病非常有用。这些活性化合物具有一般结构式##STR1## 或其体内可水解的羧基官能衍生物，其中R.sub.1和R.sub.2分别独立地代表未取代或取代的烃基或杂环烷基基团；X和Y各自独立地代表氢、可选择取代的较低烷基、卤素、氰基、羧基、较低烷氧羰基或氨基甲酰基；Q代表由8至14个碳原子组成的线性链的双基团，其中一个或多个碳原子可以被杂原子取代，该链可选择地被惰性取代基取代，其中一个或多个碳或杂原子链成员可选择地构成环结构的一部分。
• 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：——
• US4689344A
  申请人：——

  公开号：US4689344A

  公开（公告）日：1987-08-25
• Synthesis and hypolipidemic and antidiabetogenic activities of .beta.,.beta.,.beta.',.beta.'-tetrasubstituted, long-chain dioic acids
  作者：Jacob Bar-Tana、Shoshana Ben-Shoshan、Jochanan Blum、Yoelit Migron、Rachel Hertz、Johannes Pill、Gene Rose-Kahn、Ernst Christian Witte

  DOI：10.1021/jm00129a010

  日期：1989.9

  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.