5α,6β-dibromocholestan-3β-ol | 1857-80-3

• 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,6β-dibromocholestan-3β-ol
• 英文别名: 5α,6β-dibromocholesterol；5,6-dibromocholesterol；5,6β-dibromo-5α-cholestan-3β-ol；5,6β-Dibrom-5α-cholestan-3β-ol；5.6β-Dibrom-3β-hydroxy-10.13-dimethyl-17β-((R)-1.5-dimethyl-hexyl)-5α-gonan；(10R)-5t.6c-Dibrom-3c-hydroxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；5,6β-Dibrom-5α-cholestanol-(3β)；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dibromo-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-ol
• CAS: 1857-80-3
• 化学式: C₂₇H₄₆Br₂O
• 分子量: 546.47
• InChiKey: CEQDUQUVPZBDDR-RUXQDQFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  30
• 可旋转键数：
  5
• 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：

  5α,6β-dibromocholestan-3β-ol 在 三氢化钐 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到胆固醇
  参考文献：
  名称：

  脂族的还原性脱卤化VIC具有金属钐-dihalides在甲醇介质

  摘要：

  在标题反应，八个VIC -dibromides和三个亚乙烯基二溴化物，得到在室温下相应的脱溴产物（烯烃和炔烃）中性条件和氩气气氛下。2,3-二溴丁二酸衍生物产生过度还原的产物或异常的偶联二聚体。

  DOI：

  10.1016/s0040-4039(97)82951-6
• 作为产物：
  描述：

  cholesterol 在 溴 、 Petroleum ether 作用下， 生成 5α,6β-dibromocholestan-3β-ol
  参考文献：
  名称：

  Hourly Personal Exposures to Fine Particles and Gaseous Pollutants—Results from Baltimore, Maryland

  摘要：

  A study to characterize 1-hr multi-pollutant exposures was performed in Baltimore, MD, during the summer of 1998 and the winter of 1999, and was conducted over a 15-day period in each of the two seasons. Personal exposures were measured by a trained field technician, who wore a newly developed Roll-Around System (RAS) to measure 1-hr PM2.5 and gaseous (CO, O-3, NO2, SO2, volatile organic compounds [VOCs]) exposures. One-hour O-3, NO2, and SO2 personal exposures were measured using samplers developed in our laboratory, while short-term PM2.5 CO, and VOCs exposures were measured using currently available monitors. All 1-hr multi-pollutant exposures were measured while the technician performed pre-determined activities, beginning at 7:00 a.m, and ending at 7:00 p.m. of the same day. Activities were scripted to simulate activities performed by older adults (65+ years of age). Corresponding 1-hr ambient pollutant concentrations were obtained from federal or state monitoring networks.In this paper, we discuss the results from our study and present our descriptive analysis of the 1-hr personal particulate and gaseous exposure data. Personal PM2.5, O-3, CO, and VOCs exposures showed substantial variability over the 12-hr sampling periods. Multiple pairwise comparison tests showed that 1-hr personal O-3 exposures were significantly lower in indoor microenvironments as compared with outdoor microenvironments. One-hour personal CO exposures measured in vehicles were significantly higher than those measured in other microenvironments. The associations between 1-hr personal exposures and corresponding ambient concentrations differed by pollutant and by microenvironment. For example, the correlation between personal PM2.5 exposures and ambient concentrations was lowest (r = 0.36, p < 0.05) in the winter for indoor non-residential microenvironments, and was highest (r = 0.90, p < 0.05) in the winter for in-vehicle microenvironments. For O-3, the correlation between personal exposures and ambient levels was weakest in the winter for residential microenvironments (r = 0.05, p > 0.05), and was strongest in the summer for outdoor near-roadway microenvironments (r(s) = 0.91, p < 0.05).

  DOI：

  10.1080/10473289.2000.10464151

文献信息

• Reaktionen von Ph2SbH und p-TolSbH2 mit organischen Verbindungen
  作者：H.J. Breunig、J. Probst

  DOI：10.1016/s0022-328x(98)00911-5

  日期：1998.12

  p-TolSbH2 reacts with styrene with formation of ethylbenzene and (p-TolSb)n (n=4, 5 in benzene). The action of phenyl acetylene on p-TolSbH2 gives styrene. Addition of Ph2SbH on phenyl acetylene in the presence of AIBN (azodiisobutyronitrile) yields 95% trans- and 5% cis-PhCHCHSbPh2. Ph2SbH reacts with benzaldehyde in the presence of AIBN with formation of benzylalcohol (98%) and with various prochiral

  p- TolSbH 2与苯乙烯反应形成乙苯和（p- TolSb）n（苯中n = 4，5）。苯基乙炔对p- TolSbH 2的作用产生苯乙烯。的Ph加成2 SBH上在AIBN（偶氮二异丁腈）的存在下苯乙炔产生95％的反式-和5％的顺式-PhCHCHSbPh 2。在AIBN存在下，Ph 2 SbH与苯甲醛反应生成苄醇（98％），在手性助剂存在下与各种前手性酮反应，从而以高光学收率得到醇。三氯化苯与Ph 2反应在PdCl 2存在下，用SbH生成亚苄基氯。1-溴金刚烷，二溴胆固醇，2-氯苯乙酮，肉桂酰氯和氯苯乙酮与Ph 2 SbH / AIBN反应，并用氢取代卤素原子。苯甲酸苄酯是通过Ph 2 SbH / AIBN在苯甲酰氯上的作用而形成的。
• Reduction with Samarium(0). Debromination of<i>vic</i>-Dibromides to Alkenes
  作者：Reiko Yanada、Kiyoshi Bessho、Kazuo Yanada

  DOI：10.1246/cl.1994.1279

  日期：1994.7

  Three electrons from Sm(0) to Sm(III) can be available during the title reduction which was achieved in 90–95% yield with vic-dibromides such as trans-10,11-dibromodibenzosuberone, meso- and dl-1,2-dibromo-1,2-diphenylethane, ethyl 2,3-dibromo-3-phenylpropionate, 2,3-dibromo-3-phenylpropionic acid, and cholesterol dibromide. These reductions were accelerated with a catalytic amount of acid.

  在标题还原过程中，Sm(0)向Sm(III)转移三个电子的操作可以通过使用诸如反式-10,11-二溴二苯并苏勃酮、内消旋和外消旋-1,2-二溴-1,2-二苯基乙烷、乙基2,3-二溴-3-苯基丙酸酯、2,3-二溴-3-苯基丙酸以及胆固醇二溴化物等邻二溴化物来实现，产率高达90-95%。这些还原过程可通过加入少量酸催化加速。
• Water Accelerated Sm/TMSCl Reductive System: Debromination of<i>VIC</i>—Dibromides and Reduction of Sodium Alkyl Thiosulfates
  作者：Xiaoliang Xu、Ping Lu、Yongmin Zhang

  DOI：10.1080/00397910008087241

  日期：2000.6

  Abstract A simple and efficient method for the debromination of vic-dibromides to (E)-alkenes and reduction of sodium alkyl thiosulfates to disulfides promoted by Sm/TMSCl/H2O (trace) has been described.

  摘要 描述了一种在 Sm/TMSCl/H2O（痕量）促进下将 vic-二溴化物脱溴为 (E)-烯烃和将烷基硫代硫酸钠还原为二硫化物的简单有效方法。
• A Novel Strategy for the Synthesis of Bromo-Substituted Cholestenone and its New Application to a Synthesis of 1α-Hydroxycholesterol
  作者：Bin Sun、Can Jin、Weike Su

  DOI：10.3184/174751916x14652251037643

  日期：2016.7

  bromo-substituted cholestenone, including 6β-bromocholestenone and 2α,6β-dibromocholestenone. The key step in this synthesis is a very mild method for the transformation of 5α,6β-dibromocholesterol into the 6β-bromocholestenone by treatment with NaClO/NaBr/TEMPO, followed by dehydro-bromination with Et3N. Bromination at C-2 with NBS/BPO (benzoyl peroxide) gave the 2α,6β-dibromo cholestenone. This was used

  开发了一种新型高效的溴代胆甾酮的制备方法，包括6β-溴胆甾酮和2α,6β-二溴胆甾酮。该合成的关键步骤是一种非常温和的方法，通过用 NaClO/NaBr/TEMPO 处理，然后用 Et3N 进行脱溴化氢，将 5α,6β-二溴胆固醇转化为 6β-溴胆甾酮。用 NBS/BPO（过氧化苯甲酰）在 C-2 处溴化得到 2α,6β-二溴胆甾酮。这用于合成 1α-羟基胆固醇。
• Phylloerythrin: Mechanisms for cellular uptake and location, photosensitisation and spectroscopic evaluation
  作者：E Scheie、A Flåøyen、J Moan、K Berg

  DOI：10.1080/00480169.2002.36291

  日期：2002.6

  AIM To elucidate the photobiological behaviour of phylloerythrin by studying the cellular uptake and intracellular localisation pattern of phylloerythrin and its spectral properties in Chinese hamster lung fibroblast cells (V79). METHODS Phylloerythrin was diluted in dimethylsulfoxide (DMSO). Fluorescence emission and excitation spectra were measured using a luminescence spectrometer equipped with

  目的通过研究叶绿素的细胞吸收和细胞内定位模式及其在中国仓鼠肺成纤维细胞（V79）中的光谱特性，阐明叶绿素的光生物学行为。方法将菊红素稀释在二甲基亚砜（DMSO）中。使用配备有红敏光电倍增管的发光光谱仪测量荧光发射光谱和激发光谱。将V79细胞单层培养，并用0.25 microg / ml叶绿素标记，以用于摄取，细胞存活和细胞内定位研究。为了进行细胞存活和细胞内定位研究，随后将细胞以9.0 mW / cm2的通量率暴露于蓝光下。结果叶绿素在DMSO中的荧光激发光谱的特征是Soret谱带在418 nm处有最大峰。荧光发射光谱在643和706nm处具有峰。细胞中相应的光谱分别红移至422、650和712 nm。温育约10小时后，叶绿素的细胞吸收完成。摄取，活化能以及使用叶绿素在37摄氏度和0摄氏度下使用荧光显微镜观察的细胞分析表明，染料是通过扩散介导的途径吸收到细胞中的。叶绿素处理过的细胞曝光后，