5α-cholestan-3α-yl benzoate | 6030-70-2

• 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: 5α-cholestan-3α-yl benzoate
• 英文别名: 3α-benzoyloxy-5α-cholestane；3α-Benzoyloxy-5α-cholestan；Benzoesaeure-(5α-cholestanyl-(3α)-ester)；[(3R,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] benzoate
• CAS: 6030-70-2
• 化学式: C₃₄H₅₂O₂
• 分子量: 492.786
• InChiKey: YVXZAWFNDQLXBU-JYDYAICYSA-N

物化性质

• 熔点：
  100-101 °C(Solv: ethanol (64-17-5))
• 沸点：
  556.5±19.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5α-cholestan-3α-yl benzoate 在 氢氧化钾 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到5α（H）-Cholestan-3α醇
  参考文献：
  名称：

  （烷氧基亚甲基）二甲基氯化铵用羧酸盐的亲核取代：构型反转合成酯的简便方法

  摘要：

  仲醇通过与（氯亚甲基）二甲基氯化铵和苯甲酸钾的顺序反应，转化构型而转化为苯甲酸酯。

  DOI：

  10.1039/c39950001403
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 吡啶 、 乙醚 、 铂 、 苯 作用下， 生成 5α-cholestan-3α-yl benzoate
  参考文献：
  名称：

  Vavon; Jakubowicz, Bulletin de la Societe Chimique de France, 1933, vol. <4> 53, p. 581,584

  摘要：

  DOI：

文献信息

• Nucleophilic Substitution Reactions of (Alkoxymethylene)dimethylammonium Chloride
  作者：Anthony G. M. Barrett、D. Christopher Braddock、Rachel A. James、Nobuyuki Koike、Panayiotis A. Procopiou

  DOI：10.1021/jo980583j

  日期：1998.9.1

  The use of imidate esters as potential replacements for diethyl azodicarboxylate and triphenylphosphine in the Mitsunobu reaction is described. A series of secondary alcohols were allowed to react with (chloromethylene)dimethylammonium chloride, generated from dimethylformamide (DMF) and oxalyl chloride, to give imidate esters. Reaction of these salts with potassium benzoate or potassium phthalimide

  描述了在Mitsunobu反应中使用亚氨酸酯作为偶氮二羧酸二乙酯和三苯基膦的潜在替代物。使一系列仲醇与由二甲基甲酰胺（DMF）和草酰氯生成的（氯亚甲基）二甲基氯化铵反应，得到亚氨酸酯。这些盐与苯甲酸钾或邻苯二甲酰亚胺钾的反应以极好的收率得到了S（N）2取代的产物，且立体化学清晰易懂。讨论了反应条件的优化，作为通过减少所需亲核试剂的量来增加该方法的原子经济性的手段。
• 13C NMR spectral assignment of five epimeric 3α-versus 3β-functionalized cholestane pairs
  作者：S. S. Ramos、L. Santos、P. Almeida、W. B. Motherwell、M. C. Costa

  DOI：10.1002/mrc.1635

  日期：2005.10

  NMR chemical shift assignments of five α‐ and β‐ epimeric pairs of cholestanes functionalized at C‐3 are presented. Empirical increment estimations proved to be a valuable tool for the unequivocal structural elucidation when compared with the chemical shift values of cholestanes derivatized by introduction of N‐ and S‐containing groups at C‐3 in equatorial and axial positions. Moreover, the possibility

  显示了在 C-3 官能化的胆甾烷的五个 α- 和 β-差向异构对的 13C NMR 化学位移分配。与通过在赤道和轴向位置的 C-3 处引入含 N 和 S 基团而衍生的胆甾烷的化学位移值相比，经验增量估计被证明是明确结构阐明的宝贵工具。此外，证明了预期 OC(S)R 取代基在环 A 骨架的相邻碳原子上的影响的可能性。版权所有 © 2005 John Wiley & Sons, Ltd.
• Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NR′COOH
  作者：Xiao-Xin Shi、Chun-Li Shen、Jian-Zhong Yao、Liang-Deng Nie、Na Quan

  DOI：10.1016/j.tetasy.2009.12.028

  日期：2010.3

  The S(N)2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R'COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR'COOH is crucial for the S(N)2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields. (C) 2010 Elsevier Ltd. All rights reserved.
• Grochowski, Edward, Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1980, vol. 28, # 7-8, p. 489 - 497
  作者：Grochowski, Edward

  DOI：——

  日期：——
• Desorption chemical ionization mass spectrometry of epimeric 3-hydroxysteroids and derivatives. Stereoselectivity and nucleophilic substitution with ammonia
  作者：Pierre Tecon、Yutaka Hirano、Carl Djerassi

  DOI：10.1002/oms.1210170608

  日期：1982.6

  AbstractThe desorption chemical ionization mass spectra, using ammonia as reagent gas, of several epimeric 3‐hydroxysteroids and their ether and carboxylic acid ester derivatives are reported. In the case of steroids possessing a Δ4‐ or Δ5‐3α‐benzoate moiety, stereospecific stabilization of the protonated molecular ion [M+H]+ is observed. This behavior is rationalized in terms of interaction of the double bond and the protonated benzoate group at C‐3. Nucleophilic substitution by NH3 is observed when a double bond is present in the vicinity of the substitution center. The nature and the stereochemistry of the leaving group influence this substitution reaction. Our results seem to indicate the operation of a two‐step mechanism (e.g. SN1 type reaction) rather than a SN2 type mechanism for the formation of the substitution ion [MOR+NH3]+.