N'-羟基-6-甲氧基-1-苯并呋喃-2-碳杂氧杂脒 | 84965-66-2

• 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: N'-羟基-6-甲氧基-1-苯并呋喃-2-碳杂氧杂脒
• 英文名称: 3α,7α,12α-triformyloxy-5β-cholan-24-al
• 英文别名: 3,7,12-Triformoxycholan-24-al；[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-diformyloxy-10,13-dimethyl-17-[(2R)-5-oxopentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] formate
• CAS: 84965-66-2
• 化学式: C₂₇H₄₀O₇
• 分子量: 476.61
• InChiKey: ZTRYXNAUTGXGCK-XJZYBRFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N'-羟基-6-甲氧基-1-苯并呋喃-2-碳杂氧杂脒 在 氢氧化钾 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 3α,7α,12α-Trihydroxy-5β-cholesten-24-26-saeure
  参考文献：
  名称：

  胆汁酸。LXXXI。取代甲基羟基-5β-cholest-24-en-26-oates 的 E/Z 异构体的合成和结构分配

  摘要：

  甲基 3 alpha-,3 alpha,7 alpha-,3 alpha,12 alpha-和 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholest-24-en-26-的 E 和 Z 异构体的合成报告了燕麦。质谱研究显示碎片模式支持指定为 E 或 Z 异构体，尤其是侧链损失的差异。色谱程序，主要是气相色谱和高效液相色谱，支持这些分配。E 异构体在两种合成方法中的任何一种中占主导地位。

  DOI：

  10.1016/0039-128x(91)90115-c
• 作为产物：
  描述：

  3α,7α,12α-triformyloxy-5β-cholan-24-ol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以87%的产率得到N'-羟基-6-甲氧基-1-苯并呋喃-2-碳杂氧杂脒
  参考文献：
  名称：

  Improved synthesis of 5β-cholestane-3α,7α,12α, 26(27)-tetrol isomers from cholic acid

  摘要：

  Synthesis of a mixture of the 25(R) and 25(S) isomers of 5 beta-cholestane-3 alpha,7 alpha,12 alpha, 26(27)-tetrol from cholic acid in four steps, including a Wittig reaction, is described.

  DOI：

  10.1016/0039-128x(84)90027-8

文献信息

• Improved synthesis of 3α,7α,12α,24ξ -tetrahydroxy-5 β -cholestan-26-oic acid
  作者：A.K. Batta、G.S. Tint、B. Dayal、S. Shefer、G. Salen

  DOI：10.1016/0039-128x(82)90140-4

  日期：1982.6

  protected hydroxyl groups. The first method involves lithium aluminum hydride reduction of the tetrahydropyranyl ether of methyl cholate and oxidation of the resulting primary alcohol with pyridinium chlorochromate. The second method employs diborane for the reduction of the -COOH group to the -CH 2 OH group, while the third method involves the reduction of 3α, 7α, 12α -triformyloxy-5β -cholan-24-oic acid

  摘要 本文介绍了将胆酸转化为羟基受保护的胆醛的三种简单快捷的方法。第一种方法包括氢化铝锂还原胆酸甲酯的四氢吡喃醚，并用氯铬酸吡啶鎓氧化所得伯醇。第二种方法使用乙硼烷将 -COOH 基团还原为 -CH 2 OH 基团，而第三种方法涉及将 3α, 7α, 12α -triformyloxy-5β -cholan-24-oic酸（作为酰氯) 与 TMA-铁化物（四甲基氢化铁四羰基铵）直接转化为 3α, 7α, 12α -triformyloxy-5β -cholan-24-al。通过上述任何一种方法获得的醛与α-溴丙酸乙酯进行平稳的Reformatsky反应，得到3α、7α、12α、24ξ-四羟基-5β-胆甾醇-26-油酸。
• 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.
• Hadacek; Vondracek, 1947, vol. 22, p. 197,199
  作者：Hadacek、Vondracek

  DOI：——

  日期：——
• Hadacek; Vondracek, 1947, vol. 22, p. 197,200
  作者：Hadacek、Vondracek

  DOI：——

  日期：——
• Improved synthesis of 5β-cholestane-3α,7α,12α, 26(27)-tetrol isomers from cholic acid
  作者：R. Somanathan、S. Krisans

  DOI：10.1016/0039-128x(84)90027-8

  日期：1984.6

  Synthesis of a mixture of the 25(R) and 25(S) isomers of 5 beta-cholestane-3 alpha,7 alpha,12 alpha, 26(27)-tetrol from cholic acid in four steps, including a Wittig reaction, is described.