3α-formyloxy-5β-cholan-24-oic acid chloride | 4966-78-3

• 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-formyloxy-5β-cholan-24-oic acid chloride
• 英文别名: 3α-formyloxy-5β-cholan-24-oyl chloride；3α-(formyloxy)cholan-24-oyl chloride；3α-O-formylcholic acid；3α-formyloxy-5β-cholanoyl chloride-(24)；3α-Formyloxy-5β-cholansaeure-(24)-chlorid；[(3R,5R,8R,9S,10S,13R,14S,17R)-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] formate
• CAS: 4966-78-3
• 化学式: C₂₅H₃₉ClO₃
• 分子量: 423.036
• InChiKey: MCNZNCHZNIGTEH-ULCLHEGSSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  488.7±14.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-formyloxy-5β-cholan-24-oic acid chloride 在 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(3α-formyloxy-24-nor-5β-cholanyl)-4,4-dimethyl-2-oxazoline
  参考文献：
  名称：

  胆汁酰胺和恶唑啉的制备。

  摘要：

  DOI：

  10.1016/0039-128x(81)90068-4
• 作为产物：
  描述：

  3α-formyloxy-5β-cholan-24-oic acid 在 咪唑 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3α-formyloxy-5β-cholan-24-oic acid chloride
  参考文献：
  名称：

  长效避孕药：炔诺酮的胆汁酸酯

  摘要：

  描述了炔诺酮 (17 α-ethynyl-17 beta-hydroxyestr-4-en-3-one) 与三种胆汁酸的酯的合成和炔诺酮的胆甾醇碳酸酯的合成。

  DOI：

  10.1016/0039-128x(83)90103-4

文献信息

• Steroid and bile acids amide conjugates with D-glucosamine
  作者：Zdena Nováková、Jana Tomanová、Lucie Štěrbová、Pavel Drašar

  DOI：10.1135/cccc2010105

  日期：——

  New type of amide conjugates of steroid and bile acids with D-glucosamine 1 and 2 were prepared. Title compounds are prepared via acid chloride or using N-[([(1E)-1-cyano-2-ethoxy-2-oxoethylidene]amino}oxy)(dimethylamino)methylidene]-N-methylmethanaminium tetrafluoroborate as condensation agent. They were examined for gelation properties with negative results. Per-O-acetylated D-glucosamine hydrochloride was prepared in one step procedure from D-glucosamine hydrochloride by acetylation in a mixture of acetyl chloride and acetic acid.

  新型酰胺共轭物，包括类固醇和胆汁酸与D-葡萄糖胺1和2，已经制备。标题化合物是通过酸氯化物或使用N-[([(1E)-1-氰基-2-乙氧基-2-氧基乙基]氨基氧}(二甲氨基)甲基亚甲基]-N-甲基甲胺四氟硼酸盐作为缩聚剂制备的。它们被检查了凝胶化性能，结果为阴性。经过过氧化的D-葡萄糖胺盐酸盐通过在乙酸氯和乙酸混合物中乙酰化一步法从D-葡萄糖胺盐酸盐制备而成。
• Chemical synthesis
  申请人：Beth Israel Medical Center

  公开号：US04460509A1

  公开（公告）日：1984-07-17

  This invention relates to steroid compounds having a D-ring side chain structure of the formula, ##STR1## wherein R.sub.1 may be ##STR2## or --C.sub.n H.sub.2n --, wherein n is an integer from 0 to 8; Y may be S, N, or O; x is and integer of from 1 to 3; and each Z may be the same or different and is selected from the group consisting of H, OH, alkyl, aryl, aralkyl, acyloxy, cycloalkyl, substituted alkyl, substituted aryl or substituted cycloalkyl.

  这项发明涉及具有D环侧链结构的类固醇化合物，其化学式为，其中R.sub.1可以是或--C.sub.n H.sub.2n --，其中n是从0到8的整数；Y可以是S、N或O；x是1到3的整数；每个Z可以相同也可以不同，选自H、OH、烷基、芳基、芳基烷基、酰氧基、环烷基、取代烷基、取代芳基或取代环烷基的基团。
• Amphiphilic Porphinatoirons Having Steroid Groups and Their Oxygen-Adduct Formation in an Aqueous Medium
  作者：Eishun Tsuchida、Teruyuki Komatsu、Takeshi Babe、Taisaku Nakata、Hiroyuki Nishide、Hidenari Inoue

  DOI：10.1246/bcsj.63.2323

  日期：1990.8

  Amphiphilic heme derivatives having four steroid groups (steroid-heme), 5,10,15,20-tetrakis[α,α,α,α-o-[2,2-dimethyl-8-(3α-hydroxycholan-24-oyloxy)octanamido]phenyl]porphinatoiron (1b) and 5,10,15,20-tetrakis[α,α,α,α-o-(3-acetoxycholan-24-oylamino)phenyl]porphinatoiron (2b), were synthesized as a model of an oxygen carrier. They were efficiently embedded in the bilayer of a phospholipid liposome based on their high compatibility with the lipid. The oxygen-binding ability of 1b was compared with those of hemoglobin (Hb) and myoglobin (Mb). The dioxygen adduct of 1b was also characterized by Mössbauer and infrared spectroscopy.

  具有四个类固醇基团的两亲血红素衍生物（类固醇血红素），5,10,15,20-四[α,α,α,α-o-[2,2-二甲基-8-(3α-羟基胆烷-24-酰氧基)辛酰氨基]苯基]卟吩藤铁（1b）和 5、10、15、20-四[α,α,α,α-o-(3-乙酰氧基胆烷-24-酰氨基)苯基]卟吩他铁(2b)，作为氧载体的模型。由于它们与脂质高度相容，因此能有效地嵌入磷脂脂质体的双分子层中。将 1b 的氧结合能力与血红蛋白（Hb）和肌红蛋白（Mb）进行了比较。1b 的二氧加合物也通过莫斯鲍尔和红外光谱进行了表征。
• Azobenzene-bridged bile acid dimers: an interesting class of conjugates with conformation-controlled bioactivity
  作者：Weina Li、Yan Li、Xianpeng Yin、Yun Liang、Jian Li、Chen Wang、Yue Lan、Hui Wang、Yong Ju、Guangtao Li

  DOI：10.1016/j.tetlet.2016.04.107

  日期：2016.6

  The synergetic combination of the distinct properties of azobenzene and bile acid could afford stable tweezer-like conformation with tunable hydrophilic and hydrophobic channels, thus increasing their antimicrobial activity toward both Gram-positive and Gram-negative bacteria, which can be conveniently switched off when the conformation turn back to the extended state. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis and binding ability of bile acid-based receptors for recognition of flavin analogues
  作者：Prosenjit Chattopadhyay、Pramod S. Pandey

  DOI：10.1016/j.tet.2006.06.029

  日期：2006.9

  Novel cholaphanes 6a,b, based on lithocholic and deoxycholic acids, were synthesised through 3a,b by a sequence of reactions involving Cs-salt methodology of macrocyclisation. Cholaphanes 6a,b and acyclic steroidal receptors 3a,b bind flavin analogues via three hydrogen bonds in CHCl3. (c) 2006 Elsevier Ltd. All rights reserved.