3α,7α,12α-triacetoxycholanic acid chloride | 141022-98-2

• 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
• 英文名称: 3α,7α,12α-triacetoxycholanic acid chloride
• 英文别名: 3α,7α,12α-triacetoxy-5β-cholan-24-oyl chloride；[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-diacetyloxy-17-[(2R)-5-chloro-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 141022-98-2
• 化学式: C₃₀H₄₅ClO₇
• 分子量: 553.136
• InChiKey: WHEAJCZANFWTTE-SMSYYINHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  3α,7α,12α-triacetoxycholanic acid chloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 9-[2-[[4-(3α,7α,12α-bis(acetyloxy)-5β-cholan-24-oyl)-1-piperazinyl]carbonyl]phenyl]-3,6-bis(diethylamino)xanthylium chloride
  参考文献：
  名称：

  Converting bile acids into mitocans

  摘要：

  DOI：

  10.1016/j.steroids.2022.109148
• 作为产物：
  描述：

  胆酸 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 反应 24.0h， 生成 3α,7α,12α-triacetoxycholanic acid chloride
  参考文献：
  名称：

  Converting bile acids into mitocans

  摘要：

  DOI：

  10.1016/j.steroids.2022.109148

文献信息

• A convergent approach to γ-carbonyl vinyl boronates
  作者：Markus R. Heinrich、Lisa A. Sharp、Samir Z. Zard

  DOI：10.1039/b502885j

  日期：——

  γ-Carbonyl vinyl boronates can be prepared by a visible light induced radical chain addition of an S-acyl dithiocarbonate (xanthate) to the pinacol ester of vinyl boronic acid, followed by treatment with base.

  γ-碳基乙烯硼酸酯可以通过可见光诱导的自由基链加成反应，将S-酰基二硫碳酸酯（黄药）与乙烯硼酸的匹卡醇酯反应，接着再用碱处理。
• A new and efficient synthesis of trifluoromethyl ketones from carboxylic acids. Part I
  作者：Jean Boivin、Laurent El Kaim、Samir Z Zard

  DOI：10.1016/0040-4020(95)00006-t

  日期：1995.2

  Trifluoromethyl ketones can be prepared in good yield from primary carboxylic acid chlorides by reaction with pyridine and trifluoroacetin anhydride followed by aqueous work up.

  通过与吡啶和三氟乙炔酸酐反应，然后进行水性后处理，可以由伯羧酸氯化物以高收率制备三氟甲基酮。
• Synthesis of Several Hydroxylated 23-(Benzimidazol-2-yl-, Benzoxazol-2-yl and Benzothiazol-2-yl)norcholanes and Some Related Compounds
  作者：Thi Thu Huong Nguyen、Jiří Urban、Eva Klinotová、Jan Sejbal、Jiří Protiva、Pavel Drašar、Miroslav Protiva

  DOI：10.1135/cccc19950257

  日期：——

  The bile acids Ia - Id (lithocholic, chenodeoxycholic, deoxycholic, cholic) and their derivatives (O-acetylated acids and O-acetylated acid chlorides) reacted under various conditions with 1,2-diaminobenzene, 2-aminophenol and 2-aminothiophenol and afforded the title benzimidazoles II and VII, benzoxazoles V and benzothiazoles VI. Alkylation of the benzimidazole derivative IIa with 2-dimethylaminoethyl chloride resulted in 3α-hydroxy-23-[1-(2-dimethylaminoethyl)ben zimidazol-2-yl]- norcholane (IVa). The use of 1,2-diamino-4-methylbenzene enabled the preparation of 3α-acetoxy-23-[5(6)-methylbenzimidazol-2-y l]norcholane (VIII). Reactions of the 3α-hydroxy compounds IVa, Va and VIa with succinic anhydride resulted in the hemisuccinates IVi - VIi. The boric acid mediated condensation of O-acetyllithocholic acid (Ie) with 3,4-diaminopyridine gave compound X which was transformed to 3α-acetoxy-23-[1H-imidazo(4,5- c)pyridin-2-yl]norcholane (IX). The structure of the products was corroborated by the mass, IR, ¹H NMR and ¹³C NMR spectra. Some of the compounds were tested for antileukemic and for the anti-HIV activity in vitro.

  胆汁酸Ia - Id（石胆酸、烯二氧胆酸、去氧胆酸、胆酸）及其衍生物（O-乙酰化酸和O-乙酰化酸氯化物）在不同条件下与1,2-二氨基苯、2-氨基苯酚和2-氨基噻吩反应，得到了标题苯并咪唑II和VII，苯并噁唑V和苯并噻唑VI。苯并咪唑衍生物IIa与2-二甲基氨基乙基氯化物烷基化，得到3α-羟基-23-[1-(2-二甲基氨基乙基)苯并咪唑-2-基]-诺胆烷（IVa）。使用1,2-二氨基-4-甲基苯使得制备3α-乙酰氧基-23-[5(6)-甲基苯并咪唑-2-基]诺胆烷（VIII）。3α-羟基化合物IVa，Va和VIa与琥珀酸酐反应，得到半琥珀酸酯IVi - VIi。硼酸介导的O-乙酰化石胆酸（Ie）与3,4-二氨基吡啶的缩合反应产生化合物X，转化为3α-乙酰氧基-23-[1H-咪唑(4,5-c)吡啶-2-基]诺胆烷（IX）。通过质谱、红外光谱、1H核磁共振和13C核磁共振谱证实了产物的结构。部分化合物在体外进行了抗白血病和抗HIV活性测试。
• BILE ALCOHOL AND DRUG CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：TSUMURA CO., LTD.

  公开号：EP0489933A1

  公开（公告）日：1992-06-17

  A novel bile alcohol of general formula (I), having an efficacious physiological activity and being specified in the configurations of particularly the 20-, 24- and 25-positions; formula (I) wherein one of the groups R₁ and R₂ represents a group of formula (A) or (B) while the other represents -OH or -H; R₃ and R₄ represent each -CH₂OH, -CH₃ or -CH₂OSO₃Na; or alternatively R₂ and R₃ are combined together to represent -OCH₂-, R₂ and R₄ are combined together to represent -OCH₂-, or R₃ and R₄ are combined together to represent -CH₂OCH₂-; provided that R₃ and R₄ do not represent -CH₃ at the same time and that R₁ represents -OH or -H and R₂ represents the group of formula (A) or (B) when R₃ and R₄ represent -CH₂OH at the same time. A drug containing the bile alcohol, including those wherein R₃ and R₄ in the above formula (I) represent each -H, -CH₂OH, -CH₃ or -CH₂OSO₃Na (except for the case where both R₃ and R₄ represent -H at the same time), and 3α 7α, 12α, 24-tetrahydroxy-5α- or -5β-cholane is efficacious as a cerebral function protective agent, cholagogue, cell activator, microcirculation improver, antiarteriosclerotic agent, antihyperlipemia drug, hepatic function improver, anti-inflammatory drug, antithrombotic drug and hypertensive.

  通式（I）的新胆醇具有有效的生理活性，特别是在20、24和25位的构型中进行了指定。其中，R₁和R₂中的一个代表公式（A）或（B）的基团，而另一个代表-OH或-H；R₃和R₄分别代表-CH₂OH、-CH₃或-CH₂OSO₃Na；或者R₂和R₃结合在一起代表-OCH₂-，R₂和R₄结合在一起代表-OCH₂-，或者R₃和R₄结合在一起代表-CH₂OCH₂-；前提是R₃和R₄不能同时表示-CH₃，而且当R₃和R₄同时表示-CH₂OH时，R₁表示-OH或-H，R₂表示公式（A）或（B）的基团。含有胆醇的药物，包括上述公式（I）中R₃和R₄分别表示-H、-CH₂OH、-CH₃或-CH₂OSO₃Na的药物（除了R₃和R₄同时表示-H的情况），以及3α 7α，12α，24-四羟基-5α-或-5β-胆烷作为脑功能保护剂、胆汁促进剂、细胞活化剂、微循环改善剂、抗动脉硬化药、降脂药、肝功能改善剂、抗炎药、抗血栓药和降压药具有有效性。
• Amiet, R. Gary; Kalafatis, Nicole; Macrides, Theodore, Australian Journal of Chemistry, 1993, vol. 46, # 9, p. 1347 - 1354
  作者：Amiet, R. Gary、Kalafatis, Nicole、Macrides, Theodore

  DOI：——

  日期：——