cholic acid triformate | 2097-89-4

• 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: cholic acid triformate
• 英文别名: 3α,7α,12α-triformyloxy-5β-cholan-24-oic acid；(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-triformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 2097-89-4
• 化学式: C₂₇H₄₀O₈
• 分子量: 492.61
• InChiKey: OHJFKWAMNYLNEV-OCCHXLOTSA-N

物化性质

• 熔点：
  201-203 °C
• 沸点：
  593.7±50.0 °C(Predicted)
• 密度：
  1.21

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 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：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cholic acid triformate 在 lithium tri(t-butoxy)aluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 3α,7α,12α-triformyloxy-5β-cholan-24-ol
  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：

  胆酸 在 甲酸 作用下， 生成 cholic acid triformate
  参考文献：
  名称：

  Labelled bile acids

  摘要：

  本发明提供具有一般式##STR1##的化合物，其中R为##STR2##，A为0或1，B为0至4，C为0至4，Z为Se或Te，R.sup.6为--OH或氨基酸残基，R.sup.7为氢或饱和的C.sub.1至C.sub.4烷基基团，当A为1时，R.sup.8为氢或饱和的C.sub.1至C.sub.4烷基基团，N为0或1，R.sup.2、r.sup.3、r.sup.4和R.sup.5独立地为氢或α-或β-羟基团，或酮基，H.sup.5为α-或β-H。这些化合物，特别是γ放射性同位素，在研究机体功能方面具有用处。

  公开号：

  US04172085A1

文献信息

• 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。
• 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。
• Metal-Free Efficient, General and Facile Iododecarboxylation Method with Biodegradable Co-Products
  作者：Kseniya Kulbitski、Gennady Nisnevich、Mark Gandelman

  DOI：10.1002/adsc.201100145

  日期：2011.6

  The development of a novel, efficient and robust method for the general conversion of aliphatic and aromatic carboxylic acids to organic iodides without the use of heavy metals or strong oxidizing agents is reported. Commercially available N‐iodoamides were used for both initiation and halogen donation under irradiative conditions. Isolation of the product is extremely simple and the major co‐product

  据报道，在不使用重金属或强氧化剂的情况下，将脂肪族和芳香族羧酸一般转化为有机碘化物的新颖，有效和鲁棒的方法的开发。在辐照条件下，可商购获得的N-碘酰胺既用于引发反应，又用于卤素的捐赠。产品的分离非常简单，主要副产物作为水溶性生物可降解材料被去除。
• Perfluoroalkyl bile esters: a new class of efficient gelators of organic and aqueous–organic media
  作者：Supratim Banerjee、V. M. Vidya、A. J. Savyasachi、Uday Maitra

  DOI：10.1039/c1jm11912e

  日期：——

  A new class of fluorinated gelators derived from bile acids is reported. Perfluoroalkyl chains were attached to the bile acids through two different ester linkages and were synthesized following simple transformations. The gelation property of these derivatives is a function of the bile acid moiety, the spacer and the fluoroalkyl chain length. By varying these parameters, gels were obtained in aromatic hydrocarbons, DMSO and DMSO/DMF–H2O mixtures of different proportions. Several derivatives of deoxycholic and lithocholic acids were found to be efficient organogelators, while the reported bile-acid based organogelators are mostly derived from the cholic acid moiety. The efficient gelators among these compounds formed gels well below 1.0% (w/v) and hence they can be termed as supergelators. The mechanical properties of these gels could be modulated by changing either the bile acid moiety or by varying the length of the fluoroalkyl segment. The presence of CO2-philic perfluoroalkyl groups is also expected to enhance their solubility in supercritical CO2 and hence these compounds are promising candidates for making aerogels.

  报告了一类源自胆汁酸的新型氟化凝胶剂。全氟烷基链通过两种不同的酯键连接到胆汁酸，经过简单转化合成。这些衍生物的凝胶性能取决于胆汁酸部分、间隔链和氟烷基链的长度。通过改变这些参数，可以在芳香烃、DMSO以及不同比例的DMSO/DMF-H2O混合物中获得凝胶。发现几种脱氧胆酸和石胆酸的衍生物是高效的有机凝胶剂，而现有的基于胆汁酸的有机凝胶剂大多源于胆酸部分。这些化合物中高效的凝胶剂在低于1.0%（w/v）的浓度下即可形成凝胶，因此可以称之为超凝胶剂。通过改变胆汁酸部分或氟烷基段的长度，可以调节这些凝胶的机械性能。CO₂亲和的全氟烷基团的存在也预计将增强其在超临界CO₂中的溶解度，因此这些化合物在制作气凝胶方面具有很大的潜力。
• 24-nor-5β-chol-22-enes derived from the major bile acids by oxidative decarboxylation
  作者：Gerald L. Carlson、Don T.E. Belobaba、Alan F. Hofmann、Yuri Wedmid

  DOI：10.1016/s0039-128x(77)80024-x

  日期：1977.12

  The preparation of 24-nor-5beta-chol-22-enes from formyloxy-5beta-cholanic acids by oxidative decarboxylation with lead tetraacetate is described. NMR data is presented with other physical constants for the norcholenes derived from cholic, chenodeoxycholic, ursodeoxycholic, hyodeoxycholic, and deoxycholic acids. The facile synthesis of these norcholenes demonstrates the applicability of the formyloxy

  描述了通过用四乙酸铅氧化脱羧从甲酰氧基-5β-胆酸制备24-nor-5β-chol-22-烯。NMR数据与衍生自胆酸，鹅去氧胆酸，熊去氧胆酸，猪去氧胆酸和脱氧胆酸的降冰片烯的其他物理常数一起显示。这些降冰片烯的简便合成证明了甲酰氧基保护基在胆汁酸系列中对氧化脱羧的适用性。