3β-Benzamido-5-cholesten | 19595-23-4

• 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: 3β-Benzamido-5-cholesten
• 英文别名: 3β-Benzoylaminocholest-5-en；β-Benzamido-cholest-5-en；N-[(3β)-cholest-5-en-3-yl]benzamide；N-cholesteryl-benzamide；3β-Benzylamino-cholesten-(5)；N-Cholesteryl-benzamid；Benzamide, N-[(3beta)-cholest-5-en-3-yl]-；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]benzamide
• CAS: 19595-23-4
• 化学式: C₃₄H₅₁NO
• 分子量: 489.785
• InChiKey: SIRXRNBKOSZLRS-LLHZKFLPSA-N

物化性质

• 沸点：
  615.3±34.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  胆固醇 在 氯化亚砜 、 四氟化钛 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3β-Benzamido-5-cholesten
  参考文献：
  名称：

  环醇直接立体保持合成酰胺

  摘要：

  使用亚硫酰氯原位制备的亚硫酸盐与氟化钛 (IV) 的腈络合物反应，将醇一锅法转化为酰胺。首次从具有立体保留的环醇中获得酰胺。设计这些新的 Ti(IV) 反应的关键是使用很少探索的 Ti(IV) 腈配合物，这些配合物被认为可以螯合过渡态的氯亚硫酸盐以产生碳正离子，该碳正离子可通过前缘快速被腈亲核试剂捕获侧攻击机制。

  DOI：

  10.1002/ejoc.201101165

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。
• Adverse reactions associated with echinacea: the Australian experience
  作者：Raymond J. Mullins、Robert Heddle

  DOI：10.1016/s1081-1206(10)63591-0

  日期：2002.1

  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.
• 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：——
• Ryan,R.J. et al., Bulletin de la Societe Chimique de France, 1972, p. 1415 - 1419
  作者：Ryan,R.J. et al.

  DOI：——

  日期：——
• A Direct and Stereoretentive Synthesis of Amides from Cyclic Alcohols
  作者：Deboprosad Mondal、Luca Bellucci、Salvatore D. Lepore

  DOI：10.1002/ejoc.201101165

  日期：2011.12

  Chlorosulfites prepared in situ using thionyl chloride react with nitrile complexes of titanium (IV) fluoride to give a one-pot conversion of alcohols into amides. For the first time, amides are obtained from cyclic alcohols with stereoretention. Critical to the design of these new Ti(IV) reactions has been the use of little explored Ti(IV) nitrile complexes which are thought to chelate chlorosulfites

  使用亚硫酰氯原位制备的亚硫酸盐与氟化钛 (IV) 的腈络合物反应，将醇一锅法转化为酰胺。首次从具有立体保留的环醇中获得酰胺。设计这些新的 Ti(IV) 反应的关键是使用很少探索的 Ti(IV) 腈配合物，这些配合物被认为可以螯合过渡态的氯亚硫酸盐以产生碳正离子，该碳正离子可通过前缘快速被腈亲核试剂捕获侧攻击机制。