4,4'-亚丁基二[2,6-二甲苯酚] | 82583-52-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 4,4'-亚丁基二[2,6-二甲苯酚]
• 中文别名: 3,7,12-三羟基-27-羧甲基胆甾烷-26-酸
• 英文名称: 3α,7α,12α-trihydroxy-27-carboxymethyl-5β-cholestan-26-oic acid
• 英文别名: 3alpha,7alpha,12alpha-Trihydroxy-27a,27b-dihomo-5beta-cholestane-26,27b-dioic acid；2-[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl]pentanedioic acid
• CAS: 82583-52-6
• 化学式: C₂₉H₄₈O₇
• 分子量: 508.696
• InChiKey: CQHKNYMWDYUNDN-WDNAKNDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4'-亚丁基二[2,6-二甲苯酚] 、 2,2-二甲氧基丙烷 在 盐酸 、 甲醇 作用下， 以0.8 g的产率得到methyl 3α,7α,12α-trihydroxy-27-carbomethoxymethyl-5β-cholestan-26-oate
  参考文献：
  名称：

  Synthesis and 29-14C-labeling of 3α,7α,12α-trihydroxy-27-carboxymethyl-5β-cholestan-26-oic acid. A bile acid occurring in peroxisomal diseases

  摘要：

  The synthesis and C-14-labeling of 3alpha, 7alpha, 12alpha-trihydroxy-27-carboxymethyl-5beta-cholestan-26-oic acid by two different approaches is described. One of them involves chain elongation of cholic acid via Wittig-Horner condensation of its formylated 24-aldehyde with tetraethyl phosphonoglutarate. The resulting cholestenoate, on deprotection and hydrogenation, affords the unusual C29 bile acid in good yield. An alternative procedure consists in a malonic ester synthesis starting from the formylated 24-alcohol which, after conversion into a mesylate, is reacted with sodium salt of 2-carboethoxy-gamma-butyrolactone. Alkaline hydrolysis, decarboxylation, esterification with diazomethane and selective tosylation of the newly introduced primary hydroxyl function give a C28 precursor, which is easily chain-elongated into a labeled or unlabeled C29 bile acid by reaction with cyanide and hydrolysis. Due to the easy lactonization of some of the C28 intermediates, the latter method provides a better way for introducing a C-29 label than the sequence usually employed for carboxyl labeling of bile acids and consisting in a decarboxylative halogenation of the parent acid followed by substitution of the norhalogenide with [C-14]cyanide and hydrolysis. The structure of the synthesized acid or its dimethyl ester is confirmed by C-14 nuclear magnetic resonance spectroscopy and mass spectrometry, and is also shown by gas liquid chromatography to be identical with an authentic sample of biosynthetic C29 dioic bile acid extracted from body fluids of Zellweger patients.

  DOI：

  10.1016/0039-128x(93)90037-n
• 作为产物：
  描述：

  3α,7α,12α-trihydroxy-27-carboxymethyl-5β-cholest-24-en-26-oic acid 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 4,4'-亚丁基二[2,6-二甲苯酚]
  参考文献：
  名称：

  Synthesis and 29-14C-labeling of 3α,7α,12α-trihydroxy-27-carboxymethyl-5β-cholestan-26-oic acid. A bile acid occurring in peroxisomal diseases

  摘要：

  The synthesis and C-14-labeling of 3alpha, 7alpha, 12alpha-trihydroxy-27-carboxymethyl-5beta-cholestan-26-oic acid by two different approaches is described. One of them involves chain elongation of cholic acid via Wittig-Horner condensation of its formylated 24-aldehyde with tetraethyl phosphonoglutarate. The resulting cholestenoate, on deprotection and hydrogenation, affords the unusual C29 bile acid in good yield. An alternative procedure consists in a malonic ester synthesis starting from the formylated 24-alcohol which, after conversion into a mesylate, is reacted with sodium salt of 2-carboethoxy-gamma-butyrolactone. Alkaline hydrolysis, decarboxylation, esterification with diazomethane and selective tosylation of the newly introduced primary hydroxyl function give a C28 precursor, which is easily chain-elongated into a labeled or unlabeled C29 bile acid by reaction with cyanide and hydrolysis. Due to the easy lactonization of some of the C28 intermediates, the latter method provides a better way for introducing a C-29 label than the sequence usually employed for carboxyl labeling of bile acids and consisting in a decarboxylative halogenation of the parent acid followed by substitution of the norhalogenide with [C-14]cyanide and hydrolysis. The structure of the synthesized acid or its dimethyl ester is confirmed by C-14 nuclear magnetic resonance spectroscopy and mass spectrometry, and is also shown by gas liquid chromatography to be identical with an authentic sample of biosynthetic C29 dioic bile acid extracted from body fluids of Zellweger patients.

  DOI：

  10.1016/0039-128x(93)90037-n

文献信息

• Synthesis and 29-14C-labeling of 3α,7α,12α-trihydroxy-27-carboxymethyl-5β-cholestan-26-oic acid. A bile acid occurring in peroxisomal diseases
  作者：Guido G. Parmentier、Roger H. Busson、Gerard A. Janssen、Guy P. Mannaerts、Hendrik J. Eyssen

  DOI：10.1016/0039-128x(93)90037-n

  日期：1993.8

  The synthesis and C-14-labeling of 3alpha, 7alpha, 12alpha-trihydroxy-27-carboxymethyl-5beta-cholestan-26-oic acid by two different approaches is described. One of them involves chain elongation of cholic acid via Wittig-Horner condensation of its formylated 24-aldehyde with tetraethyl phosphonoglutarate. The resulting cholestenoate, on deprotection and hydrogenation, affords the unusual C29 bile acid in good yield. An alternative procedure consists in a malonic ester synthesis starting from the formylated 24-alcohol which, after conversion into a mesylate, is reacted with sodium salt of 2-carboethoxy-gamma-butyrolactone. Alkaline hydrolysis, decarboxylation, esterification with diazomethane and selective tosylation of the newly introduced primary hydroxyl function give a C28 precursor, which is easily chain-elongated into a labeled or unlabeled C29 bile acid by reaction with cyanide and hydrolysis. Due to the easy lactonization of some of the C28 intermediates, the latter method provides a better way for introducing a C-29 label than the sequence usually employed for carboxyl labeling of bile acids and consisting in a decarboxylative halogenation of the parent acid followed by substitution of the norhalogenide with [C-14]cyanide and hydrolysis. The structure of the synthesized acid or its dimethyl ester is confirmed by C-14 nuclear magnetic resonance spectroscopy and mass spectrometry, and is also shown by gas liquid chromatography to be identical with an authentic sample of biosynthetic C29 dioic bile acid extracted from body fluids of Zellweger patients.