n-butyl cholesteryl ether | 10322-03-9

• 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: n-butyl cholesteryl ether
• 英文别名: cholesterol butyl ether；cholesteryl butyl ether；3-butylcholesterol；O-butyl-cholesterol；3β-Butyloxy-cholesten-(5)；O-Butyl-cholesterin；(3S,8S,9S,10R,13R,14S,17R)-3-butoxy-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: 10322-03-9
• 化学式: C₃₁H₅₄O
• 分子量: 442.769
• InChiKey: RNIJCNIWUSGVHJ-BWVDWJPHSA-N

物化性质

• 沸点：
  507.7±29.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.935
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  n-butyl cholesteryl ether 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以66.1%的产率得到5α,6α-epoxy-3-butylcholesterol
  参考文献：
  名称：

  Synthesis and characterisation of new types of side chain cholesteryl polymers

  摘要：

  A series of cholesterol derivatives have been synthesised via the alkylation reaction of the 3-hydroxyl group with the aliphatic bromide compounds with different chain lengths. namely 3 beta-alkyloxy-cholesterol. The double bond between the C5 and C6 positions in these cholesterol derivatives was oxidised into epoxy, followed by an epoxy-ring-opening reaction with the treatment with acrylic acid, resulting in a series of 3 beta-alkyloxy-5 alpha-hydroxy-6 beta-acryloyloxycholesterol, C(n)OCh (n = 1, 2, 4, 6, 8, 10, 12), The acrylate group is connected to the C6 position, which is confirmed by the single crystal structure analysis. The corresponding polymers, PC(n)OCh, were prepared via free radical polymerisation. The structure of monomers and the resulting polymers were characterised with nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FT-IR) and gel permeation chromatography (GPC). The thermal properties of PC(n)OCh were studied using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). To determine the secondary structure of polymers, circular dichroism (CD) spectra were performed. It was found that not all monomers produce high-molecular-weight polymers because of steric hindrance. However, all polymers have a helical structure, which can be enhanced by increasing the alkoxy chain length. In addition, increasing the alkoxy chain length decreases the glass transition temperature and increases the decomposition temperature of the polymers. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.10.011
• 作为产物：
  描述：

  胆固醇 、 正丁醇 在 montmorillonite K-10 作用下， 以 氯仿 为溶剂， 反应 13.0h， 以99%的产率得到n-butyl cholesteryl ether
  参考文献：
  名称：

  Montmorillonite Clay Catalysis. Part 13.1 Etherification of Cholesterol Catalysed by Montmorillonite K-10

  摘要：

  使用蒙脱石K-10作为酸催化剂，在氯仿或环己烷中于50-70°C下进行醇和酚与胆固醇制备胆固醇醚的反应。

  DOI：

  10.1039/a803050b

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。
• The synthesis of cholesteryl alkyl ethers
  作者：G. Halperin、S. Gatt

  DOI：10.1016/0039-128x(80)90109-9

  日期：1980.1

  Seventeen cholesteryl alkyl ethers were synthesized through alcoholysis of cholesterol p-toluenesulfonate. This method was found superior to the etherification of sodium or potassium cholesterylate with alkyl halides or methanesulfonates, especially for the preparation of long-chain unsaturated aklyl ethers of [7(m)-3H]cholesterol of high specific activity.

  通过胆固醇对甲苯磺酸的醇解合成了十七种胆固醇烷基醚。发现该方法优于胆甾醇钠或胆甾醇钾与烷基卤化物或甲磺酸盐的醚化，特别是用于制备高比活性的 [7(m)-3H] 胆固醇的长链不饱和烷基醚。
• Relationship between Body Mass Index and the Use of Healthcare Services in Australia
  作者：Daniel D. Reidpath、David Crawford、Linda Tilgner、Carl Gibbons

  DOI：10.1038/oby.2002.71

  日期：2002.6

  AbstractObjective: To examine the relationship between body mass index (BMI) and the use of medical and preventive health services.Research Methods and Procedures: This study involved secondary analysis of weighted data from the Australian 1995 National Health Survey. The study was a population survey designed to obtain national benchmark information about a range of health‐related issues. Data were available from 17,033 men and 17,174 women, ≥20 years or age. BMI, based on self‐reported weight and height, was analyzed in relation to the use of medical services and preventive health services.Results: A positive relationship was found between BMI and medical service use, such as medication use, visits to hospital accident and emergency departments (for women only); doctor visits, visits to a hospital outpatient clinics; and visits to other health professionals (for women only). A negative relationship was found in women between BMI and preventive health services. Underweight women were found to be significantly less likely to have Papanicolaou smear tests, breast examinations, and mammograms.Discussion: This research shows that people who fall outside the healthy weight range are more likely to use a range of medical services. Given that the BMI of industrialized populations appears to be increasing, this has important ramifications for health service planning and reinforces the need for obesity prevention strategies at a population level.
• Cremlyn,R.J.W. et al., Phosphorus and the Related Group V Elements, 1976, vol. 6, p. 201 - 205
  作者：Cremlyn,R.J.W. et al.

  DOI：——

  日期：——
• Kutulya, L. A.; Oleinik, S. S.; Protsenko, L. I., Journal of Organic Chemistry USSR (English Translation), 1981, p. 1467 - 1469
  作者：Kutulya, L. A.、Oleinik, S. S.、Protsenko, L. I.、Tishchenko, V. G.

  DOI：——

  日期：——