3β-methyl-5α-cholestan-3α-ol | 1251-59-8

• 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-methyl-5α-cholestan-3α-ol
• 英文别名: 3-β-methyl-5α-cholestan-3α-ol；3β-methylcholestan-3a-ol；3β-methyl-5α-cholestanol-(3α)；(10S)-3t-Hydroxy-3c.10r.13c-trimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3α-Hydroxy-3β.10.13-trimethyl-17β-((R)-1.5-dimethyl-hexyl)-5α-gonan；Cholestan-3-ol, 3-methyl-, (3alpha,5alpha)-；(3R,5S,8R,9S,10S,13R,14S,17R)-3,10,13-trimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ol
• CAS: 1251-59-8
• 化学式: C₂₈H₅₀O
• 分子量: 402.704
• InChiKey: OSPYNJYSTBNWEX-FYCZTJPTSA-N

物化性质

• 熔点：
  126-127 °C
• 沸点：
  459.7±13.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3β-methyl-5α-cholestan-3α-ol 在 盐酸 、 苯 作用下， 生成 3α-chloro-3β-methyl-5α-cholestane
  参考文献：
  名称：

  Carman; Deeth, Australian Journal of Chemistry, 1970, vol. 23, p. 1053

  摘要：

  DOI：
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 4,4'-二叔丁基苯并 、 potassium tert-butylate 、 lithium 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 5.67h， 生成 3β-methyl-5α-cholestan-3α-ol
  参考文献：
  名称：

  Synthesis of functionalised enantiopure steroids from estrone and cholestanone through organolithium intermediates

  摘要：

  The reaction of epoxides I and 8 derived from estrone and cholestanone, respectively. with an excess of lithium and a catalytic amount of DTBB (7 mol%) in THF at -78 degreesC led to formation of the correlsponding beta -oxido-functionalised organolithium intermediates 2 and 9, respectively, in a regio- and stereoselective manner. Treatment of these intermediates with different electrophiles [H2O, D2O, PhCHO, Me2CO, Et2CO, (CH2)(5)CO, CO2] at -78 to 20 degreesC afforded, after hydrolysis with water. enantiomerically purr derivatives 3 and 10. respectively. When protected ketones 5 and 6 derived from D-glucose and D-fructose were used as the electrophile. the reaction with 2 gave the expected mixed products 3g and 3h, respectively. which consist of a steroid and a carbohydrate fragment. The fraction of O-protected estrone 4 as the electrophilic component and intermediate 2 afforded the C-2-symmetric steroid dimer 3f. The stereochemistry of the products was unambiguously determined by correlation with X-ray data for compound 3d and by comparison with the known compound 6a. Finally. thr addition of the dianions 13, resulting from the DTBB-catalysed lithiation of phthalan 12a and isochroman 12b, to the O-protected estrone 4 and to cholestanone 9 led to the Formation of the diols 14, 15 and 16. Diols 14 were cyclised under Mitsunobu reaction conditions to the corresponding heterocycles 17. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00121-5

文献信息

• Carboxylate-Assisted Iridium-Catalyzed C−H Amination of Arenes with Biologically Relevant Alkyl Azides
  作者：Tao Zhang、Xuejiao Hu、Zhen Wang、Tiantian Yang、Hao Sun、Guigen Li、Hongjian Lu

  DOI：10.1002/chem.201504880

  日期：2016.2.24

  wide substrate scope is reported. Benzamides with electron‐donating and ‐withdrawing groups and linear, branched, and cyclic alkyl azides are all applicable. Cesium carboxylate is crucial for both reactivity and regioselectivity of the reactions. Many biologically relevant molecules, such as amino acid, peptide, steroid, sugar, and thymidine derivatives can be introduced to arenes with high yields and

  据报道，铱催化的芳烃CHH胺化具有广泛的底物范围。具有给电子和吸电子基团以及线性，支化和环状烷基叠氮化物的苯甲酰胺均适用。羧酸铯对于反应的反应性和区域选择性都至关重要。许多生物学上相关的分子，例如氨基酸，肽，类固醇，糖和胸苷衍生物，都可以高收率和100％手性保留率引入芳烃。
• Montmorillonite K-10 and KSF as remarkable acetylation catalysts
  作者：Ai-Xiao Li、Tong-Shuang Li、Tian-Hui Ding

  DOI：10.1039/a703389c

  日期：——

  Montmorillonite K-10 and KSF catalyse the acetylation of alcohols, thiols, phenols and amines with acetic anhydride in excellent yield.

  蒙脱土K-10与KSF催化醇类、硫醇、酚类及胺类与乙酸酐的乙酰化反应，产率极佳。
• <i>p</i>-Toluenesulfonic Acid Adsorbed on Silica Gel: An Efficient Dehydrating Agent of Alcohols
  作者：Franco D'Onofrio、Arrigo Scettri

  DOI：10.1055/s-1985-31463

  日期：——

  Secondary and tertiary alcohols are efficiently dehydrated by reaction with p-toluenesulfonic acid supported on silica gel. In particular, the procedure allows the direct conversion of 3-hydroxy-steroids into Δ2-olefins or Δ3,5-dienes, without passing through the mesylate or tosylate esters.

  二级和三级醇通过与负载在硅胶上的对甲苯磺酸反应有效脱水。特别是，该方法允许将3-羟基类固醇直接转化为Δ2-烯烃或Δ3,5-二烯，而无需经过美克酸酯或对甲苯磺酸酯。
• Unprecedented stereoselectivity in the addition of organoiron(II) reagents to cyclohexanone derivatives
  作者：Manfred T. Reetz、Stephan Stanchev

  DOI：10.1039/c39930000328

  日期：——

  Various organoiron(II) reagents undergo Grignard-type additions to substituted cyclohexanone derivatives, C–C bond formation occurring stereoselectively from the equatorial direction (97–100% selectivity).

  各种有机亚铁(II)试剂对取代环己酮衍生物进行格氏型加成反应，C-C键的形成具有立体选择性，主要从赤道方向进行（选择性97-100%）。
• Ligand effects in selective carbonyl addition reactions of organomanganese and cerium reagents
  作者：Manfred T. Reetz、Helmut Haning、Stephan Stanchev

  DOI：10.1016/s0040-4039(00)60907-3

  日期：1992.11

  Transmetalation of organolithium reagents RLi (R = CH3, n-Bu) with manganese pivalate produces reagents of the type RMnOC(O)tBu which react stereoselectively with substituted cyclohexanones to afford the axial alcohols preferentially. These reagents as well as cerium ate complexes RCe(OiPr)3MgX react aldehyde-selectively in the presence of ketone functionality.

  有机锂试剂RLi（R = CH 3，n -Bu）与新戊酸锰铁的金属过渡生成类型为RMnOC（O）t Bu的试剂，该试剂与取代的环己酮发生立体选择反应，从而优先提供轴向醇。这些试剂以及铈酸盐络合物RCe（O i Pr）3 MgX在酮官能团存在下选择性地与醛发生反应。