(3S)-3α-cholestanethiol | 80312-90-9

• 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: (3S)-3α-cholestanethiol
• 英文别名: cholest-5-ene-3α-thiol；Cholest-5-en-3α-thiol；(3R,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]phenanthrene-3-thiol
• CAS: 80312-90-9
• 化学式: C₂₇H₄₆S
• 分子量: 402.728
• InChiKey: QGVQZRDQPDLHHV-VEIPTCAHSA-N

物化性质

• 熔点：
  103 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))
• 沸点：
  482.4±24.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S)-3α-cholestanethiol 在 噻吩-2-甲酸亚铜(I) 、 potassium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.08h， 生成 4-((((3R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((S)-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)thio)methyl)-1-tosyl-1H-1,2,3-triazole
  参考文献：
  名称：

  A Rh-catalyzed 1,2-sulfur migration/aza-Diels–Alder cascade initiated by aza-vinyl carbenoids from sulfur-tethered N-sulfonyl-1,2,3-triazoles

  摘要：

  一种新颖的Rh(II)催化的分子内1,2-硫迁移/分子间氮-Diels-Alder级联反应已经开发出来，有效地提供含硫的四氢吡啶衍生物。

  DOI：

  10.1039/c4cc08829h
• 作为产物：
  描述：

  3β-p-toluenesulfonyl-5α-cholest-6-one 在 吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氯氧磷 作用下， 生成 (3S)-3α-cholestanethiol
  参考文献：
  名称：

  Bourdon, Bulletin de la Societe Chimique de France, 1958, p. 1117

  摘要：

  DOI：

文献信息

• Stereoselective Synthesis of δ-Lactones from 5-Oxoalkanals via One-Pot Sequential Acetalization, Tishchenko Reaction, and Lactonization by Cooperative Catalysis of Samarium Ion and Mercaptan
  作者：Jue-Liang Hsu、Jim-Min Fang

  DOI：10.1021/jo016058t

  日期：2001.12.1

  sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis

  通过sa离子和硫醇的协同催化，一系列5-氧代烷醛以有效和立体选择性的方式转化为（取代的）δ-内酯。这一一锅法包括一系列缩醛化，Tishchenko反应和内酯化。与醇相比，有意使用硫醇有利于促进催化循环。提出了反应机理和立体化学，并得到了一些实验证据的支持。sa离子/硫醇共催化反应显示出远程控制的特征，适用于旋光性δ-内酯的不对称合成。这项研究还证明了两种昆虫信息素（2S，5R）-2-甲基己内酯和（R）-十六烷内酯的合成，
• NEW SYNTHETIC REACTIONS BASED ON 1-METHYL-2-FLUOROPYRIDINIUM SALTS. STEREOSPECIFIC PREPARATION OF THIOALCOHOLS FROM ALCOHOLS
  作者：Ko Hojo、Hiroshi Yoshino、Teruaki Mukaiyama

  DOI：10.1246/cl.1977.437

  日期：1977.4.5

  Treatment of various alcohols with 1-methyl-2-fluoropyridinium salt and sodium N,N-dimethyldithiocarbamate afforded alkykl N,N-dimethyldithiocarbamates of inverted configuration. The latter compounds were converted to thioalcohols with retention.

  用 1-甲基-2-氟吡啶鎓盐和 N,N-二甲基二硫代氨基甲酸钠处理各种醇类，可得到倒置构型的 N,N-二甲基二硫代氨基甲酸烷基酯。后一种化合物被转化为硫醇并保留下来。
• Metal-free reductive desulfurization of C-sp³-substituted thiols using phosphite catalysis
  作者：Rana M. I. Morsy、Ganesh Samala、Ankur Jalan、Michael E. Kopach、Naresh M. Venneti、Jennifer L. Stockdill

  DOI：10.1039/d3sc00045a

  日期：——

  that is catalytic in phosphine/phosphite has not been reported. Here, we report the successful merging of two thermal radical processes: the desulfurization of unactivated and activated alkyl thiols and the reduction of P(V) = S to P(III) by reaction with a silyl radical species. We employ catalytic trimethyl phosphite, catalytic azo-bis(cyclohexyl)nitrile, and two equivalents of tris(trimethylsilyl)silane

  由于 P S 键的强度，膦和亚磷酸盐是非金属脱硫方法的关键工具。这些方法的首要前提是反应需要化学计量（或过量）的 P( III ) 试剂。尽管经过了数十年的研究，但在磷化氢/亚磷酸盐中催化的脱硫过程尚未见报道。在这里，我们报告了两个热自由基过程的成功合并：未活化和活化烷基硫醇的脱硫以及通过与甲硅烷基自由基反应将 P( V ) = S还原为 P( III )。我们采用催化亚磷酸三甲酯、催化偶氮双(环己基)腈和两当量的三(三甲基甲硅烷基)硅烷作为化学计量还原剂和硫原子清除剂。该方法能够耐受常见的有机官能团，并且能够以良好至优异的产率提供产品。
• Dimerization Inhibitors of HIV-1 Protease Based on a Bicyclic Guanidinium Subunit
  作者：Perla Breccia、Nicole Boggetto、Ruth Pérez-Fernández、Michiel Van Gool、Masayuki Takahashi、Loïc René、Pilar Prados、Bernard Badet、Michèle Reboud-Ravaux、Javier de Mendoza

  DOI：10.1021/jm030871u

  日期：2003.11.1

  Original inhibitors of HIV-1 protease based on a chiral bicyclic guanidinium scaffold linked to short peptidic mimics of the terminal protease sequences and to a lipophilic group were designed. These inhibitors prevent dimerization of the native protease by an interfacial structure at the highly conserved antiparallel beta-strand involving both the N and C termini that substantially account for dimerization. The preorganized guanidinium spacer introduces additional electrostatic hydrogen-bonding interactions with the C-terminal Phe-99 carboxylate. Lipophilic residues linked to side chains and the guanidinium scaffold are essential for dimerization inhibition as ascertained by Zhang kinetics (4, K-id = 290 nM; 6 or 6', K-id = 150 nM; 8, K-id = 400 nM) combined with a circular dichroism study on the enzyme thermal stability. Remarkably, less hydrophobic compounds result in mixed dimerization (1a and 3) or active site inhibitors (5). Removal of the guanidinium hydrophobic groups leads to less active or inactive ligands.
• VOLANTE R. P., TETRAHEDRON LETT., 1981, 22, NO 33, 3119-3122
  作者：VOLANTE R. P.

  DOI：——

  日期：——