24-<2-(4,4-dimethyl)-2-oxazolinyl>-5β-25,26,27-trinor-cholestane-3α,6α-diol | 95511-28-7

• 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
• 英文名称: 24-<2-(4,4-dimethyl)-2-oxazolinyl>-5β-25,26,27-trinor-cholestane-3α,6α-diol
• 英文别名: 2-(3α,6α-dihydroxy-24-nor-5β-cholanyl)-4,4-dimethyl-2-oxazoline；24-[2-(4,4-dimethyl)-2-oxazolinyl]-5β-25,26,27-trinor-cholestane-3α,6α-diol；Hyodeoxyoxazoline；(3R,5R,6S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)butan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
• CAS: 95511-28-7
• 化学式: C₂₈H₄₇NO₃
• 分子量: 445.686
• InChiKey: GDHKZXQQQIMYAM-UYYKWOEPSA-N

物化性质

• 沸点：
  547.0±25.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  24-<2-(4,4-dimethyl)-2-oxazolinyl>-5β-25,26,27-trinor-cholestane-3α,6α-diol 在 吡啶 、 苯亚硒酸 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 33.0h， 生成 methyl 22,23-didehydrohyodeoxycholate
  参考文献：
  名称：

  Studies on steroidal plant-growth regulator 25. Concise stereoselective construction of sidechain of brassinosteroid from the intact sidechain of hyodeoxycholic acid: formal syntheses of brassinolide, 25-methylbrassinolide, 26, 27-bisnorbrassinolide and their related compounds

  摘要：

  A concise stereoselective construction of sidechain of brassinolide (1), 25-methylbrassinolide (3) and 26,27-bisnorbrassinolide (4), which involves beta-alkylative 1,3- carbonyl transposition of the alpha,beta-unsaturated ketones 11 and 34 and alpha, beta-unsaturated methyl ester 26, using the intact sidechain of hyodeoxycholic acid (2) as starting material, is described. The formal syntheses of 1, 3 and 4 were accomplished. In the mean time, 25-methylcastasterone (21), 26,27-bisnortyphasterol (6) and the new 25-methyltyphasterol (5) were also syntehesized.

  DOI：

  10.1016/s0040-4020(01)88509-4
• 作为产物：
  描述：

  猪去氧胆酸 在 sodium hydroxide 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 24-<2-(4,4-dimethyl)-2-oxazolinyl>-5β-25,26,27-trinor-cholestane-3α,6α-diol
  参考文献：
  名称：

  胆汁酰胺和恶唑啉的制备。二。熊去氧胆酸，脱氧胆酸，猪去氧胆酸和胆酸的酰胺和恶唑啉的合成。

  摘要：

  胆汁酰胺和恶唑啉是通过一系列步骤合成的，这些步骤包括游离胆汁酸与甲酸反应生成甲酰氧基衍生物，制备甲酰氧基酰氯，酰氯与2-氨基-2-甲基-氯的缩合。 1-丙醇得到酰胺，最后用亚硫酰氯将酰胺环化得到恶唑啉。通过物理常数，薄层色谱和气液色谱法对恶唑啉进行表征，并通过元素分析和气液色谱-质谱法对其进行鉴定。一些胆汁酸恶唑啉衍生物可在体外改变细菌7-脱羟基酶的活性，并在纯培养物中抑制某些厌氧菌的生长。

  DOI：

  10.1016/0039-128x(82)90011-3

文献信息

• Studies on steroidal plant-growth regulator 25. Concise stereoselective construction of sidechain of brassinosteroid from the intact sidechain of hyodeoxycholic acid: formal syntheses of brassinolide, 25-methylbrassinolide, 26, 27-bisnorbrassinolide and their related compounds
  作者：Wei-Shan Zhou、Liang-Fu Huang

  DOI：10.1016/s0040-4020(01)88509-4

  日期：1992.1

  A concise stereoselective construction of sidechain of brassinolide (1), 25-methylbrassinolide (3) and 26,27-bisnorbrassinolide (4), which involves beta-alkylative 1,3- carbonyl transposition of the alpha,beta-unsaturated ketones 11 and 34 and alpha, beta-unsaturated methyl ester 26, using the intact sidechain of hyodeoxycholic acid (2) as starting material, is described. The formal syntheses of 1, 3 and 4 were accomplished. In the mean time, 25-methylcastasterone (21), 26,27-bisnortyphasterol (6) and the new 25-methyltyphasterol (5) were also syntehesized.
• The preparation of bile acid amides and oxazolines, II, the synthesis of the amides and oxazolines of ursodeoxycholic acid, deoxycholic acid, hyodeoxycholic acid and cholic acid
  作者：Bertram I. Cohen、Patricia S. May、Charles K. McSherry、Erwin H. Mosbach

  DOI：10.1016/0039-128x(82)90011-3

  日期：1982.12

  Bile acid amides and oxazolines were synthesized by a sequence of steps involving the reaction of the free bile acid with formic acid to yield the formyloxy derivative, preparation of the formyloxy acid chloride, condensation of the acid chloride with 2-amino-2-methyl-1-propanol to give the amide and, finally, cyclization of the amide with thionyl chloride to give the oxazoline. The oxazolines were

  胆汁酰胺和恶唑啉是通过一系列步骤合成的，这些步骤包括游离胆汁酸与甲酸反应生成甲酰氧基衍生物，制备甲酰氧基酰氯，酰氯与2-氨基-2-甲基-氯的缩合。 1-丙醇得到酰胺，最后用亚硫酰氯将酰胺环化得到恶唑啉。通过物理常数，薄层色谱和气液色谱法对恶唑啉进行表征，并通过元素分析和气液色谱-质谱法对其进行鉴定。一些胆汁酸恶唑啉衍生物可在体外改变细菌7-脱羟基酶的活性，并在纯培养物中抑制某些厌氧菌的生长。