dicholest-5-en-3β-yl disulfide | 39879-87-3

• 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: dicholest-5-en-3β-yl disulfide
• 英文别名: cholesteryl disulfide；dicholesteryl disulfide；Dicholesteryl-disulfid；Dicholesterylsulfid；(3S,8S,9S,10R,13R,14S,17R)-3-[[(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]disulfanyl]-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]phenanthrene
• CAS: 39879-87-3
• 化学式: C₅₄H₉₀S₂
• 分子量: 803.441
• InChiKey: APEMORXGJOVAIW-MALNHOFLSA-N

物化性质

• 熔点：
  141-143 °C
• 沸点：
  780.9±40.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.19
• 重原子数：
  56.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  dicholest-5-en-3β-yl disulfide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以219 mg的产率得到(3S,8S,9S,10R,13R,14S,17R)-3-[[(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]sulfinylsulfanyl]-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]phenanthrene
  参考文献：
  名称：

  A new procedure for the conversion of thiols into reactive sulfenylating agents

  摘要：

  Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3. Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with beta-diketones to afford sulfides. This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise reactive thiols.

  DOI：

  10.1021/jo00023a039
• 作为产物：
  描述：

  hexafluoro-l6-phosphane, 2-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)disulfaneyl)-1-ethylpyridin-1-ium salt 在 四丁基碘化铵 作用下， 以80%的产率得到dicholest-5-en-3β-yl disulfide
  参考文献：
  名称：

  A new procedure for the conversion of thiols into reactive sulfenylating agents

  摘要：

  Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3. Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with beta-diketones to afford sulfides. This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise reactive thiols.

  DOI：

  10.1021/jo00023a039

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。
• Benn et al., Journal of the Chemical Society, 1958, p. 2800,2804
  作者：Benn et al.

  DOI：——

  日期：——
• Electrochemical synthesis of glycoconjugates from activated sterol derivatives
  作者：Aneta M. Tomkiel、Jan Kowalski、Jolanta Płoszyńska、Leszek Siergiejczyk、Zenon Łotowski、Andrzej Sobkowiak、Jacek W. Morzycki

  DOI：10.1016/j.steroids.2014.01.007

  日期：2014.4

  Several derivatives of cholesterol and other 3 beta-hydroxy-Delta(5)-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors. (C) 2014 Elsevier Inc. All rights reserved.
• Wagner-Jauregg; Lennartz, Chemische Berichte, 1941, vol. 74, p. 27,31
  作者：Wagner-Jauregg、Lennartz

  DOI：——

  日期：——
• Transvesicular reactions of thiols with Ellman's reagent
  作者：Robert A. Moss、Shanti Swarup

  DOI：10.1021/jo00260a013

  日期：1988.12