5α-cholestane-3β,5,6β-triol 3,6-diacetate | 1260-68-0

• 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: 5α-cholestane-3β,5,6β-triol 3,6-diacetate
• 英文别名: 5α-cholestane-3β,5,6β-triol-3,6-diacetate；cholestane-3β,5α,6β-triol 3,6-diacetate；cholestane-3β,5α,6β-triol diacetate；5α-hydroxycholestane-3β,6-diyl diacetate；3β.6β-diacetoxy-5α-cholestanol-(5)；5α-Cholestan-3β,5α,6β-triol-3.6-diacetat；5Alpha-cholestane-3beta,5,6beta-triol 3,6-diacetate；[(3S,5R,6R,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: 1260-68-0
• 化学式: C₃₁H₅₂O₅
• 分子量: 504.751
• InChiKey: FSOSLUNLZBKXMA-ZJBXHLDWSA-N

物化性质

• 熔点：
  165-166 °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：

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

  残留燃油燃烧产生的细颗粒物质的特征。

  摘要：

  在732千瓦的锅炉中对四种不同的残留燃油进行了燃烧实验。通过旋风分离器将空气中的PM排放物样品空气分离成标称直径小于和大于2.5微米的馏分。但是，通过计算机控制的扫描电子显微镜（CCSEM）检查了几个样品，发现PM2.5部分的一部分由碳质空心球和直径最大为10微米的囊泡颗粒组成。在S，V，Ni，Fe，Cu，Zn和As K边缘以及Pb L边缘获得X射线吸收精细结构（XAFS）光谱数据。对S光谱的X射线吸收近边缘结构（XANES）区域进行反卷积，可以确定S的主要分子形式是硫酸盐（占总S的26-84％）和噻吩（占总S的13-39％）。PM2.5样品中的硫酸盐含量大于PM2.5 +样品中的硫酸盐含量。无机硫化物和元素硫的含量较低。所有样品的Ni XANES光谱与NiSO4的光谱非常吻合，而大多数V光谱与硫酸氧钒（VO.SO4.xH2O）的光谱非常相似。研究的其他金属（例如，Fe，Cu，Zn和Pb）也主要以硫酸盐形式存在。砷以砷（As

  DOI：

  10.1080/10473289.2000.10464157
• 作为产物：
  描述：

  cholesterol 在 双氧水 、 溶剂黄146 作用下， 生成 5α-cholestane-3β,5,6β-triol 3,6-diacetate
  参考文献：
  名称：

  On the estimation of 'an implicitly additive demand system'

  摘要：

  Motivated by a lack of Engel flexibility in commonly used demand systems, Rimmer and Powell developed a new demand system. This system, referred to AIDADS, is implicitly, directly additive, possesses marginal budget shares and thus Engel elasticities, that vary nonlinearly with expenditure such that predicted budget shares are restricted to the [0,1] interval. Due to these attractive Engel properties, AIDADS represents a significant contribution to the literature on demand analysis. This paper presents an alternative estimation procedure to the one used by Rimmer and Powell and examines its properties via a case study. The proposed approach avoids a linear approximation employed in Rimmer and Powell's estimation framework. Based on a small Monte Carlo study, it appears that the approach produces more accurate estimates of the parameters and Engel elasticities.

  DOI：

  10.1080/00036840050155832

文献信息

• The kinetic effects of substituted benzoates on the Westphalen rearrangement
  作者：D.N. Kirk

  DOI：10.1016/0040-4020(75)80172-4

  日期：1975.1

  The rate of the Westphalen rearrangement of 3β,6β-disubstituted 5α-cholestan-5-ols is influenced by substituted benzoates at the 6β position in a manner which can be correlated with Hammett substituent constants (σ), giving a reaction constant (ρ) of −0·35.

  3β，6β-二取代的5α-胆甾烷-5-醇的Westphalen重排速率受6β位置上的取代苯甲酸酯影响，其影响方式可与哈米特取代基常数（σ）相关，从而得到反应常数（ρ）为-0·35。
• Dissolving metal reduction of esters to alkanes. A method for the deoxygenation of alcohols
  作者：Anthony G. M. Barrett、Christopher R. A. Godfrey、David M. Hollinshead、Panayiotis A. Prokopiou、Derek H. R. Barton、Robin B. Boar、Laurette Joukhadar、James F. McGhie、Satish C. Misra

  DOI：10.1039/p19810001501

  日期：——

  Diverse carboxylic esters have been reduced with dissolving Group 1A metals. Using lithium in ethylamine, sterically hindered esters (RCO2R′) were deoxygenated giving the alkane (R′H) whereas non-hindered esters regenerated the parent alcohol (R′OH). This permitted the selective deoxygenation of diesters. Conversely, potassium–sodium eutectic solubilised with 18-crown-6 in t-butylamine and tetrahydrofuran

  溶解1A族金属可还原各种羧酸酯。使用乙胺中的锂，将位阻酯（RCO 2 R'）脱氧，得到烷烃（R'H），而无阻酯则再生出母体醇（R'OH）。这允许二酯的选择性脱氧。相反，用18-crown-6溶解于叔丁胺和四氢呋喃（THF）中的钾钠共晶可有效地对受阻酯和非受阻酯进行脱氧。在室温下不存在亲核试剂的情况下，羧酸酯基团阴离子的主要反应是脱氧。
• Photo-induced transformations. Part 51. Photo- and thermally-induced rearrangements of hypoiodites of steroidal homoallyl alcohols. The formation of some oxygen heterocycles via photo- and thermally-induced rearrangements of 3-hydroxy-Δ⁵-steroid hypoiodites in the presence of mercury(<scp>II</scp>) oxide and iodine
  作者：Hiroshi Suginome、Akio Furusaki、Kimitoshi Kato、Norio Maeda、Fumihiko Yonebayashi

  DOI：10.1039/p19810000236

  日期：——

  Hypoiodites of cholesterol and epicholesterol in benzene containing mercury(II) oxide and iodine underwent photo-induced rearrangement to give 3α,5-epoxy-6β- and -6α-iodo-A-homo-4-oxa-5α-cholestanes (3) and (4), together with 3-formyloxy-2-iodo-A-nor-2,3-secocholest-5-ene (2). Stereochemistry of the epoxide (3) was established by an X-ray crystallographic analysis. When the reaction of cholesterol

  在苯含汞（胆固醇和epicholesterol的次碘酸盐II）氧化物和碘后行光致重排，得到3α，5-环氧- 6β-和-6α碘-阿-homo -4-氧杂- 5α-胆甾烷（3） （4）与3-甲酰氧基-2-碘-A -nor-2,3-secocholest-5-烯（2）一起。通过X射线晶体学分析确定了环氧化物（3）的立体化学。当胆固醇次碘酸根的反应在55-60℃下，只有6β异构体热引起的，伴随着胆甾-5-烯3α基甲-homo -4- oxacholest -5-烯3α基醚（ 20），形成了-homo-4-oxacholest-5-en-3α-ol（21）。碘代环氧化合物（3）或（4）的催化氢解反应得到3α，5-环氧-A-homo-4-oxa-5β-胆甾烷（16）经三氟化硼-乙醚-乙酸酐处理后转化为2-乙酰基-5-乙酰氧基甲基-4-oxa-5β-胆甾-2-烯（29）苯。
• 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）。
• Synthesis of Oxygenated Cholesterols as Structural Mimics of Phorbol Ester-Type Tumor Promoters.
  作者：Yasuyuki ENDO、Hiroshi FUKASAWA、Yuichi HASHIMOTO、Koichi SHUDO

  DOI：10.1248/cpb.42.462

  日期：——

  beta-5 alpha,6 beta-tetrol (8), was also synthesized. Among these analogs, compound 7 showed weak TPA-like activities in three biological tests: inhibition to protein kinase C and to cytosolic-nuclear tumor promoter-binding protein (CN-TPBP), and induction of differentiation of human promyelocytic leukemia cells (HL-60) to monocyte-like cells. On the other hand, compound 5 was found to be a specific ligand

  我们设计了几种氧化类固醇，其中包括疏水基团的官能团的排列方式类似于佛波酯（12-O-十四烷酰phorbol-13-乙酸酯，TPA），目的是发现具有TPA样活性但具有不同的骨骼和刚性构象。设计的类固醇1个β，5个α-二羟基-3β-羟甲基胆甾醇-6（1），3个β，5个α-二羟基胆甾醇6个（5），3个β-羟甲基胆甾醇5个α-ol-6合成一个（6）和1个β，3个β，5个α-三羟基胆甾醇-6个（7）。还合成了从软珊瑚中分离得到的一种相关的氧化类固醇，胆固醇1β，3β-5α，6β-四醇（8）。在这些类似物中，化合物7在三个生物学测试中显示出弱的TPA样活性：抑制蛋白激酶C和胞质核肿瘤启动子结合蛋白（CN-TPBP），并诱导人早幼粒细胞白血病细胞（HL-60）分化为单核细胞样细胞。另一方面，发现化合物5是CN-TPBP的特异性配体，但是缺乏其他TPA样活性。

表征谱图