cholesterin | 34026-89-6

• 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: cholesterin
• 英文别名: cholesterol；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2S)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 34026-89-6
• 化学式: C₂₇H₄₆O
• 分子量: 386.662
• InChiKey: HVYWMOMLDIMFJA-PAMFVNDTSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  480.6±14.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cholesterin 在 Jones reagent 、 溴 、 sodium acetate 、 草酸 、 溶剂黄146 、 锌 作用下， 以 乙醚 、 丙酮 为溶剂， 生成 cholest-4-en-3-one
  参考文献：
  名称：

  Structural elucidation, density functional calculations and contribution of intermolecular interactions in cholest-4-en-3-one crystals: Insights from X-ray and Hirshfeld surface analysis

  摘要：

  The foremost objective of the present work is systematic analysis of intermolecular interactions in crystal structure of cholest-4-en-3-one (2) molecule. It is accomplished by Hirshfeld surface analysis and fingerprint plot. Hirshfeld surface analysis has been used to visualize the fidelity of the crystal structure. This method permitted for the identification of individual types of intermolecular contacts and their impact on the complete packing. Molecules are linked by a combination of C=O-H, C-H-H, and C-H contacts, which have clear signatures in the fingerprint plots. The theoretical study was attempted to predict the optimized geometry and computed spectra by the Density Functional Theory (DFT) using the B3LYP function with the 6-311++G(d,p) basis set. Atomic charges, MEP mapping, HOMO-LUMO, various thermodynamic and molecular properties have been reported. In addition thermal stability, optical, morphological, and microstructral properties of the title compound (2) have also been explored. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.12.027
• 作为产物：
  描述：

  (20R)-22-Oxo-23,24-dinor-5-cholen-3β-yl-acetat 在 Pd-BaSO₄ 氢氧化钾 、 氢气 、 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 100.5h， 生成 cholesterin
  参考文献：
  名称：

  Sucrow, Wolfgang; Nooy, Michael van, Liebigs Annalen der Chemie, 1982, # 10, p. 1897 - 1906

  摘要：

  DOI：

文献信息

• Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 13. A novel synthesis of benzyl ethers
  作者：Anthony G. M. Barrett、Roger W. Read、Derek H. R. Barton

  DOI：10.1039/p19800002184

  日期：——

  Benzyl ethers were prepared from alcohols by reaction with chloro(phenylmethylene)dimethylammonium chloride and sodium hydrogen telluride in sequence. The salt (1)[Me2NC(R1)OR2Cl–; R1= H, R2= cholest-5-en-3β-yl] and sodium borohydride gave the borane complex of 3β-dimethylaminomethoxycholest-5-ene. Salt (1; R1= Ph, R2= cholest-5-en-3β-yl or 5α-cholestan-3β-yl) and ammonia or hydrazine gave the steroidal

  通过依次与氯（苯基亚甲基）二甲基氯化铵和碲化氢钠反应，由醇制得苄基醚。盐（1）[我2 NC（R 1）OR 2氯- ; R 1＝ H，R 2＝胆甾-5-烯-3β-基]，硼氢化钠得到3β-二甲基氨基甲氧基胆甾-5-烯的硼烷配合物。盐（1； R 1 = Ph，R 2 =胆甾-5-en-3β-基或5α-胆甾-3β-基）和氨或肼得到甾族苯甲酸酯或苯甲酰肼酸盐。
• A versatile cobalt(II)-Schiff base catalyzed oxidation of organic substrates with dioxygen: Scope and mechanism
  作者：T Punniyamurthy、Beena Bhatia、M.Madhava Reddy、Golak C Maikap、Javed Iqbal

  DOI：10.1016/s0040-4020(97)00432-8

  日期：1997.6

  Cobalt(II) complex 1a-f derived from Schiff bases act as efficient catalysts during the oxidation of wide range of organic substrates(e.g. alkenes, alcohols, benzylic compounds and aliphatic hydrocarbons) with dioxygen in the presence of aliphatic aldehydes or ketones or ketoesters. EPR studies on 1a-f complexes suggest that the aliphatic carbonyl compounds promote the formation of a cobalt(III)-superoxo

  在脂肪族醛或酮或酮酸酯的存在下，席夫碱衍生的钴（II）配合物1a-f在多种有机底物（例如烯烃，醇，苄基化合物和脂肪族烃）与双氧的氧化作用中充当有效的催化剂。对1a-f配合物的EPR研究表明，脂族羰基化合物可促进形成负责有机化合物氧化的钴（III）-超氧代物种。这些研究还证明了钴上的配体在控制这些氧化的化学选择性中的作用。还为这些氧化提供了合理的机械原理。
• Synthesis of Ester-Substituted Indolo[2,1-<i>a</i>]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions
  作者：Jian-Qiang Chen、Xiaodong Tu、Binyan Qin、Shaoxin Huang、Jun Zhang、Jie Wu

  DOI：10.1021/acs.orglett.1c04082

  日期：2022.1.21

  A direct alkoxycarbonylation/cyclization reaction is accomplished under visible light-induced photoredox catalysis. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in good to excellent yields. It is worth noting that this method not only can afford the synthesis of indolo[2,1-a]isoquinolines but also can provide an alternative route for generating complex

  在可见光诱导的光氧化还原催化下完成直接的烷氧羰基化/环化反应。使用这种方法，可以以良好至优异的产率制备多种酯取代的吲哚[2,1- a ]异喹啉。值得注意的是，该方法不仅可以合成吲哚[2,1- a ]异喹啉，还可以为生成带有羧酸酯的复杂目标结构提供替代途径。
• Selective aromatization of the A ring of steroids through demethylation by an electrophilic ruthenium fragment
  作者：Francisco Urbanos、Juan Fernandez-Baeza、Bruno Chaudret

  DOI：10.1039/c39910001739

  日期：——

  The reaction of ‘(C5Me5)Ru+’, produced by the protonation of [(C5Me5)RuOMe]2 by CF3SO3H, with various steroids leads to selective aromatization of the A ring via demethylation of the 19 methyl group and/or dehydration and/or dehydrogenation reactions.

  CF 3 SO 3 H通过[（C 5 Me 5）RuOMe] 2的质子化反应产生的'（C 5 Me 5）Ru + '与各种类固醇的反应导致A环通过甲基化而选择性芳香化19甲基和/或脱水和/或脱氢反应。
• New Observations on Deprotection of O-Benzyl Derivatives with Pd/C-Cyclohexene
  作者：Vimal Sansanwal、H. G. Krishnamurty

  DOI：10.1080/00397919508015865

  日期：1995.7

  Abstract Palladium catalysed transfer hydrogenation using cyclohexene as the donor is found to deprotect readily alcohol benzyl ethers and aliphatic benzyl esters. The phenol benzyl ethers and benzyl benzoates are stable under these conditions.

  摘要 发现使用环己烯作为供体的钯催化转移氢化可以轻松地对醇苄基醚和脂肪族苄基酯进行脱保护。苯酚苄基醚和苯甲酸苄酯在这些条件下是稳定的。