3β-Acetamidocholest-5-en | 14412-92-1

• 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: 3β-Acetamidocholest-5-en
• 英文别名: N-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]acetamide
• CAS: 14412-92-1
• 化学式: C₂₉H₄₉NO
• 分子量: 427.714
• InChiKey: NIJKPJNXBCARQP-VEVYEIKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3β-Acetamidocholest-5-en 在 氢氧化钾 作用下， 生成 (3b)-胆甾-5-烯-3-胺
  参考文献：
  名称：

  conessine的组成。第八部分 胆固醇甲苯-对磺酸盐与液氨的反应

  摘要：

  DOI：

  10.1039/jr9550000986
• 作为产物：
  描述：

  (NZ)-N-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]hydroxylamine 在 乙醇 、 sodium 作用下， 生成 3β-Acetamidocholest-5-en
  参考文献：
  名称：

  Adverse reactions associated with echinacea: the Australian experience

  摘要：

  Background: Fifty percent of Australians use complementary and alternative medicines (other than vitamins) in any 12-month period, of which echinacea-containing products are increasingly popular. Recent reports have highlighted the risk of allergic reactions to complementary medicines in atopic patients.Objective: To determine the characteristics of adverse reactions linked to use of the popular herbal remedy echinacea.Methods: Five privately referred patients were evaluated by the authors in their office practice via skin prick testing (SPT) on the volar aspect of the forearm and radioallergosorbent test after adverse reactions to echinacea. As there was little published information on adverse reactions to echinacea, reports to the Australian Adverse Drug Reactions Advisory Committee were reviewed. Those suggestive of possible allergic reactions were evaluated in greater detail by anonymously surveying the healthcare professionals who had reported the cases and from one unreported case. Serum was collected for further analysis where possible.Results: Five cases of adverse reactions to echinacea were personally evaluated by the authors. Two patients suffered anaphylaxis and a third had an acute asthma attack 10 minutes after their first ever dose of echinacea. The fourth patient suffered recurrent episodes of mild asthma each time echinacea was ingested, and the fifth developed a maculopapular rash within 2 days of ingestion which recurred when rechallenged. Three of the patients had positive SPT results. Three reported repeated spontaneous "challenges" and symptoms after further ingestion of echinacea. Fifty-one Australian adverse drug reports implicating echinacea were also reviewed. There were 26 cases suggestive of possible immumoglobulin E-mediated hypersensitivity (4 anaphylaxis, 12 acute asthma, 10 urticaria/angioedema). Of these 26 patients, age ranged from 2 to 58 years, 78% were female and >50% were known to be atopic. Four were hospitalized, 4 reacted after their first known exposure, and I patient suffered multiple progressive systemic reactions. Twenty percent of 100 atopic subjects who had never taken echinacea also had positive SPT results to this substance when tested by one of the authors in his office practice.Conclusion: Some atopic subjects have positive SPT results to echinacea in the absence of known exposure. Atopic subjects are also overrepresented in those experiencing reactions to echinacea. The possibility that cross-reactivity between echinacea and other environmental allergens may trigger allergic reactions in "echinacea-naYve" subjects is supported by the Australian data. Given its widespread (and largely unsupervised) community use, even rare adverse events become inevitable. Atopic patients should be cautioned appropriately.

  DOI：

  10.1016/s1081-1206(10)63591-0

文献信息

• Der dipolar aprotisch-protische Lösungsmitteleffekt bei der nucleophilen Substitution des Cholesteryltosylats
  作者：Alfred Bertho

  DOI：10.1002/jlac.19687140116

  日期：1968.7.23

  Die nucleophile Substitution des Cholesteryltosylats (1) durch die Nucleophile N3⊖, SCN⊖, Br⊖, J⊖ und Dimethylamin in protischen und aprotischen Medien wird untersucht. Der aprotisch-protische Effekt wird bei N3⊖ und SCN⊖ beobachtet; er ist bei Dimethylamin wahrscheinlich, fehlt aber bei Br⊖ und J⊖. – Unter den Nebenprodukten der Substitution finden sich Steroid-Verbindungen (Tabb. 1–5 ), die zum Teil

  胆甾醇的亲核取代甲苯磺酸酯（1）通过亲核试剂Ñ 3 ⊖，SCN ⊖，溴⊖，J ⊖和在质子和非质子媒体二甲胺进行了研究。非质子-质子作用与N-观察到3 ⊖和SCN ⊖ ; 它很可能为二甲胺，但缺少溴⊖和J ⊖。-取代的副产物包括类固醇化合物（表1-5），其中一些以新的形成形式出现。-将结果与有关阴离子的可溶性和非质子溶剂对阳离子的可溶性的信息进行比较。
• STEROIDS: III. THE EPIMERIC N-ACETYL-3-AMINOCHOLEST-4- AND -5-ENES
  作者：R. A. B. Bannard、A. F. McKay

  DOI：10.1139/v55-137

  日期：1955.6.1

  Lithium aluminum hydride reduction of the oximes of 3-ketocholest-4- and -5-enes gave mixtures of amines. These amines on acetylation and separation gave respectively N-acetyI-3(α)-aminocholest-5-ene, N-acetyl-3(β) aminocholest-5-ene, N-acetyl-3(α)-aminocholest-4-ene, and N-acetyl-3(β)-aminocholest-4-ene. The N-acetyl-3(α)-aminocholest-5-ene (m.p. 184.5 °C.) was shown to be identical with the cholesterylacetamide obtained by the acetylation of the degradation product from N-benzyl-3(α)-aminocholest-5-ene (m.p. 90-91 °C).

  3-酮胆甾-4-烯和-5-烯的肟经过氢化铝锂还原后，产生了混合胺。这些胺在乙酰化和分离后分别得到N-乙酰基-3（α）-氨基胆甾-5-烯，N-乙酰基-3（β）氨基胆甾-5-烯，N-乙酰基-3（α）-氨基胆甾-4-烯和N-乙酰基-3（β）-氨基胆甾-4-烯。N-乙酰基-3（α）-氨基胆甾-5-烯（熔点184.5℃）被证明与从N-苯甲基-3（α）-氨基胆甾-5-烯（熔点90-91℃）的降解产物乙酰化得到的胆固醇乙酰胺相同。
• Unusual electrochemical oxidation of cholesterol
  作者：Jan Kowalski、Zenon Łotowski、Jacek W. Morzycki、Jolanta Płoszyńska、Andrzej Sobkowiak、Agnieszka Z. Wilczewska

  DOI：10.1016/j.steroids.2008.01.014

  日期：2008.5

  It has been found that cholesterol undergoes direct electrochemical oxidation on platinum electrode in dichloromethane. Voltammetric measurements show that the process is controlled by the rate of electron transfer and the height of the oxidation peak is linear us. concentration of cholesterol. Preparative electrolysis with separated cathodic and anodic compartments afforded dicholesteryl ether in a relatively high material yield. Depending on electrolysis conditions (composition of supporting electrolyte and electrolytic cell construction) various by-products with a 3 beta-chloro, 3 beta-acetoxy, or 3 beta-acetylamino group were obtained. (C) 2008 Elsevier Inc. All rights reserved.
• Barton,D.H.R. et al., Journal of the Chemical Society. Perkin transactions I, 1974, p. 2101 - 2107
  作者：Barton,D.H.R. et al.

  DOI：——

  日期：——
• Steroids and walden inversion. Part XXII. The configuration of cholesterylamine
  作者：J. H. Pierce、C. W. Shoppee、G. H. R. Summers

  DOI：10.1039/jr9550000690

  日期：——