5β-cholan-3α-ol | 5352-77-2

• 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: 5β-cholan-3α-ol
• 英文别名: 5beta-Cholan-3alpha-ol；(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-pentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 5352-77-2
• 化学式: C₂₄H₄₂O
• 分子量: 346.597
• InChiKey: ODFHHECDCZZICL-LYWYBQTLSA-N

物化性质

• 沸点：
  428.4±13.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  25
• 可旋转键数：
  3
• 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：

  5β-cholan-3α-ol 生成 5β-cholan-3β-ol
  参考文献：
  名称：

  Klein,H.; Djerassi,C., Chemische Berichte, 1973, vol. 106, p. 1897 - 1904

  摘要：

  DOI：
• 作为产物：
  描述：

  3α,12α,24-trihydroxy-5β-cholane 反应 2.0h， 生成 5β-cholan-3α-ol
  参考文献：
  名称：

  Klein,H.; Djerassi,C., Chemische Berichte, 1973, vol. 106, p. 1897 - 1904

  摘要：

  DOI：

文献信息

• Tris(3,6-dioxaheptyl)amine: A superior complexing agent for dissolving metal reactions
  作者：Ajay K. Bose、Pietro Mangiaracina

  DOI：10.1016/s0040-4039(00)95452-2

  日期：1987.1

  Commercially available tris(3,6-dioxaheptyl)amine (TDA-1) is an effective phase transfer catalyst for reactions with sodium-potassium alloy in tetrahydrofuran. Deoxygenation of acetates, dehalogenation, and hydrolysis of tosylates and mesylates proceed in high yield. The use of a deuterated alcohol during deoxygenation reactions leads to site-specific deuteration.

  市售的三（3,6-二氧杂庚基）胺（TDA-1）是一种有效的相转移催化剂，可与钠-钾合金在四氢呋喃中反应。乙酸酯的脱氧，脱卤代以及甲苯磺酸酯和甲磺酸酯的水解以高收率进行。在脱氧反应中使用氘代酒精会导致特定位置的氘代。
• Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters
  作者：Sarwat Chowdhury、Robert F. Standaert

  DOI：10.1021/acs.joc.6b01699

  日期：2016.10.21

  Primary alcohols can be deoxygenated cleanly and in yields of 60–95% by reduction of derived diphenyl phosphate esters with lithium triethylborohydride in tetrahydrofuran at room temperature. Selective deoxygenation of a primary alcohol in the presence of a secondary alcohol was demonstrated. The two-step process can be performed in one pot, making it simple and convenient.

  通过在室温下在四氢呋喃中用三乙基硼氢化锂还原衍生的磷酸二苯酯，可以对伯醇进行干净的脱氧，收率60-95％。证明了在仲醇存在下伯醇的选择性脱氧。两步过程可以在一个锅中进行，使其简单方便。
• Genetic and management factors that influence the susceptibility of cattle to<i>Mycobacterium bovis</i>infection
  作者：Clive J. C. Phillips、Charles R. W. Foster、Pat A. Morris、Rachel Teverson

  DOI：10.1079/ahrr200236

  日期：2002.6

  Genetic variation in the susceptibility of cattle toMycobacterium bovisinfection exists in differences between families and species, but not breeds. Susceptibility toM. bovisinfection increases with age of cattle. Natural exposure toM. bovisor environmental mycobacteria may assist in the development of specific immunity, but there is no direct evidence for such immunological priming of tuberculosis resistance in cattle. This has, however, been demonstrated in humans and other animals. Since non-specific mechanisms have a role in protective immunity, developing an effective vaccine will be difficult, even though some protection of other species has been achieved. Immunological suppression in the periparturient period can produce anergic reactors, which may act as a constant source of infection for cattle-to-cattle transmission. Circumstantial evidence suggests that an adequate intake of mineral, vitamin and protein reduces the susceptibility of cattle. Although weather patterns have been implicated in the susceptibility of herds toM. bovisinfection, there is insufficient information to determine the risk factors precisely. It is concluded that some reduction in the susceptibility of cattle toM. bovisinfection can be achieved by modifications to the management system to minimize risk factors, but that a considerable amount of further research is required.

  摘要 牛对牛分枝杆菌感染敏感性的遗传变异存在家系和物种之间的差异，但不存在品种之间的差异。对牛分枝杆菌感染的易感性随牛的年龄而增加。牛分枝杆菌环境分枝杆菌的自然暴露可能有助于特异性免疫力的发展，但目前还没有直接证据表明牛对结核病的抵抗力是由这种免疫启动的。不过，这在人类和其他动物身上得到了证实。由于非特异性机制在保护性免疫中发挥作用，因此，尽管其他物种已经获得了一定程度的保护，但开发有效疫苗仍将十分困难。围产期的免疫抑制会产生过敏反应者，这可能成为牛与牛之间传播的持续感染源。间接证据表明，摄入充足的矿物质、维生素和蛋白质可降低牛的易感性。虽然天气模式与牛群对牛海绵状瘤病毒感染的易感性有关，但没有足够的信息来准确确定风险因素。结论是，通过调整管理系统以尽量减少风险因素，可在一定程度上降低牛群对牛海绵状瘤病毒感染的易感性，但仍需开展大量的进一步研究。
• Methanesulfonate Esters of Cholane1 Alcohols1All cholane derivatives mentioned in this paper ere 5β-cholanca.
  作者：Frederic C. Chang

  DOI：10.1002/jps.2600530904

  日期：1964.9

  Some methanesulfonate esters of cholane alcohols derived from desoxycholic acid have been prepared and submitted for screening as antitumor agents. Infrared spectra of the dimesylates have distinctive patterns in the 870 to 1000 cm. −1 region, each of which is shown to be virtually superimposable on a composite spectrum of a pair of corresponding mono-mesylates. Antitumor screening test results indicate

  已经制备了一些由脱氧胆酸衍生的胆甾醇的甲磺酸酯，并将其作为抗肿瘤剂进行筛选。二甲基化产物的红外光谱在870至1000厘米范围内具有独特的图案。-1区，每个区显示为实际上可重叠在一对相应的单甲磺酸酯的复合光谱上。抗肿瘤筛选测试结果表明3α，12α-和12α，24化合物对测试动物无活性且无害，但3α，24-异构体的毒性却很大。
• Translational energy release and stereochemistry of steroids. IX-The mechanism of the elimination of water from metastable ions in epimeric 3-hydroxy steroids of the 5β-series
  作者：Z. V. I. Zaretskii、J. M. Curtis、A. G. Brenton、J. H. Beynon、Carl Djerassi

  DOI：10.1002/oms.1210230606

  日期：1988.6

  AbstractThe mechanism of water elimination from metastable molecular and [M − CH3˙]+ ions, as well as from ions deprived of ring D, in epimeric 3‐hydroxy steroids of the 5β‐series has been elucidated by deuterium labelling, by the measurements of the translational energy released during loss of water, and by collision‐induced decomposition mass‐analysed ion kinetic energy spectrometry. It was found that the dehydration of the metastable molecular ion in 3α‐hydroxy steroids of the 5β‐series occurs mostly regiospecifically as an elimination of the 3α‐hydroxyl together with the 9α‐hydrogen atom. The ring A in the molecular ion has to flip to the boat conformation to make this reaction possible. In the metastable molecular ion of 3β‐hydroxy steroids of the 5β‐series a different dehydration mechanism operates, with very little participation of the 9α‐hydrogen atom. The mechanisms of water loss from metastable [M − CH3˙]+ ions and from ions deprived of ring D differ from that of the molecular ion.