cholestane-3β,5α,6α-triol 3,6-diacetate | 7199-72-6

• 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: cholestane-3β,5α,6α-triol 3,6-diacetate
• 英文别名: 3β,6α-Diacetoxy-5α-cholestan；3β,6α-Diacetoxy-5α-hydroxy-cholestan；3β,6α-diacetoxy-5α-cholestan-5-ol；3β.6α-Diacetoxy-5α-cholestanol-(5)；[(3S,5R,6S,8S,9S,10R,13R,14S,17R)-6-acetyloxy-5-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 7199-72-6
• 化学式: C₃₁H₅₂O₅
• 分子量: 504.751
• InChiKey: FSOSLUNLZBKXMA-ZFQULLPCSA-N

物化性质

• 熔点：
  186 °C(Solv: methanol (67-56-1))
• 沸点：
  544.7±35.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cholestane-3β,5α,6α-triol 3,6-diacetate 在 吡啶 、 氢氧化钾 、 氯化亚砜 作用下， 生成 3β,6α-dihydroxy-4-ene-cholestane
  参考文献：
  名称：

  Technical efficiency of European railways: a distance function approach

  摘要：

  This study has two principal objectives. The first objective is to measure and compare the performance of European railways. The second objective is to illustrate the usefulness of econometric distance functions in the analysis of production in multi-output industries, where behavioural assumptions such as cost minimization or profit maximization, are unlikely to be applicable. Using annual data on 17 railways companies during 1988-1993, multioutput distance functions are estimated using corrected ordinary least squares (COLS). The resulting technical efficiency estimates range from 0.980 for the Netherlands to 0.784 for Italy, with a mean of 0.863. The distance function results are also compared with those obtained from single-output production functions, where aggregate output measures are formed using either total revenue or a Tornqvist index. The results obtained indicate substantial differences in parameter estimates and technical efficiency rankings, casting significant doubt upon the reliability of these single-output models, particularly when a total revenue measure is used to proxy aggregate output.

  DOI：

  10.1080/00036840050155896
• 作为产物：
  描述：

  cholesterol 在 四氧化锇 、 乙醚 、 苯 作用下， 生成 cholestane-3β,5α,6α-triol 3,6-diacetate
  参考文献：
  名称：

  Uschakow; Ljutenberg, Zhurnal Obshchei Khimii, 1939, vol. 9, p. 69,71

  摘要：

  DOI：

文献信息

• 19-nor-5β-Methyl-steroide, III. Die Acetolyse von 3-Methoxy-steroiden
  作者：Günther Snatzke

  DOI：10.1002/jlac.19656860120

  日期：1965.7.15

  y-Δ4-cholesten (III), 3β.6β-Diacetoxy-Δ4-cholesten (V) und dessen 3α-Epimeres (IVb) identifiziert werden. IV b und V entstehen durch Acetolyse aus dem 3β-Methoxy-Derivat III. Das 6-Monoacetat (VIc) des 5α-Cholestan-3α.5.6β-triols liefert mit SOCl2 ein cyclisches Sulfit VII, das 3-Monoacetat VId das entsprechende 5α.6α-Epoxyd IXb. Die Acetolyse gesättigter und ungesättigter 3β- und 3α-Methoxy-steroide

  的副产物3β甲氧基6β乙酰氧基5α胆甾-5-醇的重排威斯特法伦存在的（Ib）中可能是3β甲氧基6β乙酰氧基Δ的三个4 -cholesten（III），3β。 6β-二乙酰氧基Δ 4 -cholesten（V）和其3α差向异构体（IVb）中被识别。IV b和V通过3β-甲氧基衍生物III的乙酰化作用形成。5α-胆甾烷-3α.5.6β-三醇的6-单乙酸盐（VIc）为SOCl 2提供环状亚硫酸盐VII，3-单乙酸盐VId提供相应的5α.6α-环氧化物IXb。KHSO 4或SnCl 4对饱和和不饱和3β-和3α-甲氧基类固醇的乙酰化作用在相同条件下，在乙酸酐中加入3，3-乙氧基化合物和甲醇消除产物的量各不相同，而胆固醇甲醚在相同条件下仅产生胆固醇乙酸酯。3β-甲氧基-19-的反应也不-5β甲基Δ 9 -cholesten-6β醇（IIa）中进行了描述。
• An Approach to the Synthesis of Electron-Rich and Hindered Esters and Its Application to the Synthesis of Acteoside
  作者：Xiaojuan Zhang、Yutong Yang、Fuye Wang、Zhengbing Zhou、Hongbin Zhang、Yugen Zhu

  DOI：10.1021/acs.orglett.1c03528

  日期：2021.12.3

  distributed in natural products and play a central role in bioactivities. Herein, we disclose an efficient, mild, and general esterification approach to the synthesis of these esters by employing gold(I)-catalyzed acylation reaction with alkyne-tethered mixed anhydrides and alcohols. This method can be applied to ester-bond formation in complex substrates and facilitates efficient synthesis of acteoside

  富含电子的酯类普遍存在于天然产物中，并在生物活性中发挥核心作用。在此，我们公开了一种有效、温和且通用的酯化方法，通过采用金 (I) 催化的酰化反应与炔烃连接的混合酸酐和醇来合成这些酯。该方法可应用于复杂底物的酯键形成，并有助于高效合成属于苯乙醇苷家族的acteoside，具有广泛的生物活性。
• Pyridine-idnduced dishielding of 4-methylene protons for the determination of C-6 stereochemistry of sterols having a 5.ALPHA.,6-diol moiety. Revision of the C-6 stereochemistry of marine sterol isolated from a sponge, Dysidea sp.
  作者：YOSHINORI FUJIMOTO、TAKETOSHI YAMADA、NOBUO IKEKAWA

  DOI：10.1248/cpb.33.3129

  日期：——

  The utility of the proton nuclear magnetic resonance method involving pyridine-induced deshielding was demonstrated for stereochemical assignment at the C-6 position of sterols having a 5α, 6ζ-diol moiety. Thus, the 4α-hydrogen resonance of 6α-isomers such as cholest-7-ene-3β, 5α, 6α-triol (8) is observed at ca. 3.0 ppm, whereas the 4β-hydrogen resonance of 6β-isomers such as cholest-7-ene-3β, 5α, 6β-triol (10) is observed at ca. 3.0 ppm. This method was applied to a marine sterol (4) isolated from a sponge, Dysidea sp., and it was concluded that the structure should be revised to the 6α-isomer (5) rather than the reported 6β-isomer (4).

  通过吡啶诱导去屏蔽的质子核磁共振方法，展示了在具有5α, 6β-二醇基团的甾醇C-6位的立体化学分配中的应用。因此，像胆甾-7-烯-3β, 5α, 6α-三醇（8）这样的6α-异构体的4α-氢共振在大约3.0 ppm处被观察到，而像胆甾-7-烯-3β, 5α, 6β-三醇（10）这样的6β-异构体的4β-氢共振同样在大约3.0 ppm处被观察到。该方法被应用于从海绵Dysidea sp.分离出的海洋甾醇（4），并得出结论，结构应修订为6α-异构体（5），而非报告的6β-异构体（4）。
• Windaus, Chemische Berichte, 1907, vol. 40, p. 257,259
  作者：Windaus

  DOI：——

  日期：——
• 627. Steroids and related compounds. Part VII. Some derivatives of 5-methyl-10-norandrost-8(9)-ene-3 : 6-diol-17-one
  作者：M. Davis、V. Petrow

  DOI：10.1039/jr9490002973

  日期：——