5α,6α-epoxy-cholestan-3β-ol benzoate | 51646-05-0

• 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,6α-epoxy-cholestan-3β-ol benzoate
• 英文别名: benzoic acid-(5,6α-epoxy-5α-cholestan-3β-yl ester)；Benzoesaeure-(5,6α-epoxy-5α-cholestan-3β-ylester)；3β-Benzoyloxy-5,6α-epoxy-5α-cholestan；[(1S,2R,5S,7R,9S,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-yl] benzoate
• CAS: 51646-05-0
• 化学式: C₃₄H₅₀O₃
• 分子量: 506.769
• InChiKey: ZSGQVYLOLWOUMN-SOCHMZHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α,6α-epoxy-cholestan-3β-ol benzoate 在 氢氧化钾 、 potassium acetate 作用下， 生成 5α-cholestane-3β,5,6β-triol 3,6-diacetate
  参考文献：
  名称：

  Long-Term Monitoring and Analysis of Hourly Solar UV Radiation in the 290-380 nm Range in the Middle Region of Saudi Arabia

  摘要：

  The UV and global solar radiation on a horizontal surface at ground level in Riyadh City (latitude 24 degrees 34' N, longitude 46 degrees 43' E) have been measured and analyzed. Measurements of UV radiation (295-385 nm) were recorded every 10 min for five years (January 1983-December 1987). The maximum recorded hourly mean irradiance UV radiation was 28 W/m(2) and occurred in July, while the minimum was 14 W/m(2) in December. A steady monthly value of K-vh = (UV/H) was obtained and equaled 2.9%. A similar trend was found for the monthly variation of K-t = (H/H-o) and K-v = (UV/H-o) Maximum values of 90% and 2.6% were recorded in June for K-t and K-v, respectively, while minimum values of 35% and 1%, respectively, were obtained in December. A linear correlation was obtained between K-v and K-t. These findings were discussed and connected to the meteorological events. The results were compared with the regions of Kuwait, Bahrain, Dhahran, and Makkah.

  DOI：

  10.1080/10473289.2000.10464148
• 作为产物：
  描述：

  胆固醇苯甲酸酯 在 单过氧邻苯二甲酸 、 乙醚 、 氯仿 作用下， 生成 5α,6α-epoxy-cholestan-3β-ol benzoate
  参考文献：
  名称：

  164. β -胆固醇氧化

  摘要：

  DOI：

  10.1039/jr9430000613

文献信息

• Manganese (III) acetate dihydrate catalyzed aerobic epoxidation of unfunctionalized olefins in fluorous solvents
  作者：K.S. Ravikumar、Francis Barbier、Jean-Pierre Bégué、Danièle Bonnet-Delpon

  DOI：10.1016/s0040-4020(98)00396-2

  日期：1998.6

  for the epoxidation of various olefins with molecular oxygen/pivalaldehyde as an oxidant in perfluoro-2-butyltetrahydrofuran. Various types of olefins, including substituted styrenes, stilbenes and cyclic and acyclic alkenes were epoxidized in excellent yields at 25°C. The reaction is stereodependent. Regioselectivity is observed on epoxidation of limonene. Mono- and disubstituted olefins show interesting

  乙酸锰（III）二水合物用作催化剂，用于在全氟-2-丁基四氢呋喃中用分子氧/新戊醛作为氧化剂对各种烯烃进行环氧化。各种类型的烯烃，包括取代的苯乙烯，对苯二甲酸酯，环状和无环烯烃，都在25°C下以优异的收率进行了环氧化。该反应是立体依赖性的。在柠檬烯的环氧化中观察到区域选择性。单取代和二取代的烯烃在含氟溶剂如全氟-2-丁基四氢呋喃和1,1,1,3,3,3-六氟-2-丙醇中的反应性显示出令人感兴趣的二分法。
• β-Selective Epoxidation of Cholesterol Derivatives with Molecular Oxygen and Aldehyde Catalyzed by Manganese(II) Complex
  作者：Tohru Yamada、Kiyomi Imagawa、Teruaki Mukaiyama

  DOI：10.1246/cl.1992.2109

  日期：1992.11

  In the presence of a catalytic amount of bis(dipivaloylmethanato)manganese(II) (= Mn(dpm)2), various cholesterol derivatives are smoothly converted into the corresponding β-epoxides in good to high yields with combined use of molecular oxygen and isobutyraldehyde. These stereoselectivities are the reversal of the cases using peracid such as mCPBA.

  在使用催化量的双(二戊酰甲酮酸)锰(II)（= Mn(dpm)2）的存在下，多种胆固醇衍生物能够顺利地转化为相应的高产率至高产率的β-环氧化物，这需要结合分子氧和异丁醛的使用。这些立体选择性与使用过酸如mCPBA的情况相反。
• Alternative Selective Oxidation Pathways for Aldehyde Oxidation and Alkene Epoxidation on a SiO₂-Supported Ru−Monomer Complex Catalyst
  作者：Mizuki Tada、Satoshi Muratsugu、Mutsuo Kinoshita、Takehiko Sasaki、Yasuhiro Iwasawa

  DOI：10.1021/ja9079513

  日期：2010.1.20

  We have prepared a novel Ru-mononer complex supported on a SiO(2) surface by using a Ru-monomer complex precursor with a p-cymene ligand, which was found to be highly active for the selective oxidation of aldehydes and the epoxidation of alkenes using O(2). The structure of the supported Ru catalyst was characterized by means of FT-IR, solid-state NMR, diffuse-reflectance UV/vis, XPS, Ru K-edge EXAFS

  我们通过使用带有 p-伞花烃配体的 Ru-单体复合前体制备了一种支持在 SiO(2) 表面上的新型 Ru-单体复合物，发现该配体对醛的选择性氧化和烯烃的环氧化具有高度活性使用 O(2)。通过 FT-IR、固态 NMR、漫反射 UV/vis、XPS、Ru K-edge EXAFS 和 DFT 计算表征了负载的 Ru 催化剂的结构，这表明形成了孤立定位的不饱和 Ru中心在 Ru 络合物前体的对伞花烃配体后面。SiO(2) 上的现场隔离 Ru-单体复合物实现了巨大的 TON（周转数），用于醛和烯烃的选择性氧化；例如，在环境温度下，选择性异丁醛 (IBA) 氧化为 38,800,000 吨，反式二苯乙烯环氧化为 2,100,000 吨，据我们所知，它们是金属络合物催化中最高的 TON 之一。我们还发现，活化能为 48 kJ mol(-1) 的 IBA 单独氧化比活化能为 99 kJ mol(-1)
• Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols
  作者：Ke-Yin Ye、Terry MCallum、Song Lin

  DOI：10.1021/jacs.9b04993

  日期：2019.6.19

  exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely, bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti

  有机自由基通常是具有异常高反应性的短寿命中间体。从战略上讲，实现由有机自由基介导的合成有用的转化需要有效的引发和选择性终止事件。在这里，我们报告了一种新的催化策略，即双金属自由基氧化还原继电器，用于环氧化物向烯丙醇的区域和立体选择性重排。这种方法利用了 Ti 和 Co 配合物的丰富氧化还原化学，并将还原性环氧化物开环（引发）与氢原子转移（终止）相结合。至关重要的是，在影响关键的成键和断裂事件时，Ti 和 Co 催化剂彼此进行质子转移/电子转移以实现周转，从而构成真正协同的双催化系统。
• Surface Functionalization of Supported Mn Clusters to Produce Robust Mn Catalysts for Selective Epoxidation
  作者：Satoshi Muratsugu、Zhihuan Weng、Mizuki Tada

  DOI：10.1021/cs400053f

  日期：2013.9.6

  A robust heterogeneous Mn catalyst for selective epoxidation was prepared by the attachment of a Mn4 oxonuclear complex [Mn4O2(CH3COO)7(bipy)2](ClO4)·3H2O (1) on SiO2 and the successive stacking of SiO2-matrix overlayers around a supported Mn cluster. The structures of supported Mn catalysts were characterized by means of FT-IR spectroscopy, diffuse-reflectance UV/vis spectroscopy, Raman spectroscopy

  通过将Mn 4氧核配合物[Mn 4 O 2（CH 3 COO）7（bipy）2 ]（ClO 4）·3H 2 O（1）附着在SiO 2和SiO 2-基体覆盖层在支撑的Mn团簇周围的连续堆叠。通过FT-IR光谱，漫反射紫外/可见光谱，拉曼光谱，X射线光电子能谱和Mn K边缘X射线吸收精细结构对负载的Mn催化剂的结构进行了表征。CH 3之间的配体交换反应1和表面硅烷醇基团的COO配体产生了SiO 2负载的Mn团簇（2），其配位结构与1相似。的随后的加热2在真空下得到的负载的Mn簇（3，4至CH的部分消除）3 COO配体。的表面附着的Mn簇2，3和4很容易释放到环氧化条件下的反应液（浸出的Mn：约50％），尽管它们为活性的环氧化反式-芪（转化反-二苯乙烯-99％，反式-二苯乙烯环氧化物的选择性96％，在3上反应6小时。我们发现表面上的SiO 2-基体覆盖层对2上支持的Mn团簇的功能化改变了所支持的