3β-acetoxy-6-fluorocholest-5-ene | 75676-29-8

• 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: 3β-acetoxy-6-fluorocholest-5-ene
• 英文别名: 6-fluorocholesteryl acetate；6-fluoro-5-cholesten-3β-ol acetate；6-fluorocholesterol acetate；[(3S,8S,9S,10R,13R,14S,17R)-6-fluoro-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 75676-29-8
• 化学式: C₂₉H₄₇FO₂
• 分子量: 446.689
• InChiKey: YLERYUKJFJZGKB-XGRWYXQASA-N

物化性质

• 沸点：
  494.4±38.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-6-fluorocholest-5-ene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 0.08h， 以44%的产率得到6-fluoro-7α-bromocholesteryl acetate
  参考文献：
  名称：

  Synthesis of 6-fluorovitamin D3

  摘要：

  DOI：

  10.1021/jo00212a001
• 作为产物：
  描述：

  3β-acetoxy-5β-cholestan-6-one 在 diethylaminoethyl sulphuric trifluoride 、 硫酸 作用下， 以 乙二醇二甲醚 为溶剂， 以73%的产率得到3β-acetoxy-6-fluorocholest-5-ene
  参考文献：
  名称：

  新型合成固醇探针对无细胞和细胞系统中胆固醇代谢酶的影响。

  摘要：

  合成了一系列新型固醇，作为细胞内胆固醇代谢的两种重要酶，酰基辅酶A：胆固醇酰基转移酶（ACAT）和胆固醇7α-羟化酶的酶和细胞功能的探针。化合物是6-氟-5-胆固醇-3β-醇（6-氟胆固醇），7-胆固醇-3β-醇（7-胆固醇），6-β-氟胆固醇3β-醇（6β-氟胆固醇） ，3-乙酰氧基-6-氟胆甾醇-3β-醇（3-乙酰氧基-6-氟胆甾醇）和7-甲氧基-5-胆甾烯-3β-醇（7-甲氧基胆固醇）。设计它们的目的是揭示固醇结构的微小变化（特别是环结构某些部分的反应性和极性）对酶活性和细胞内胆固醇代谢的影响。3β-羟基对于与两种酶相互作用必不可少，因为3-乙酰氧基-6-氟胆甾醇不影响任何酶催化的反应。6-氟胆固醇和7-胆固醇对胆固醇酯化没有影响，但确实抑制了胆固醇的羟基化，其他具有可能影响7位的基团的化合物也是如此，即6-β-氟胆固醇和7-甲氧基胆固醇。在无细胞和细胞ACAT活性测定中，氟胆甾醇都

  DOI：

  10.1016/0009-3084(96)02593-5

文献信息

• Preparation of vinylene fluorides
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04212815A1

  公开（公告）日：1980-07-15

  A ketone is reacted with an N,N-disubstituted-aminosulfur trifluoride in the presence of a polar solvent, preferably also in the presence of a polar catalyst, to produce a vinylene fluoride. Exemplary is the reaction of cholestan-3.beta.-ol-6-one-3-t-butyl ether with diethylaminosulfur trifluoride in the presence of fuming sulfuric acid and tetrahydrofuran to produce 6-fluorocholesterol.

  在极性溶剂存在下，最好还要有极性催化剂的情况下，酮与N,N-二取代氨基硫三氟化物反应，产生乙烯基氟化物。例如，以胆甾醇-3-β-醇-6-酮-3-叔丁基醚为反应物，在浓硫酸和四氢呋喃的存在下，与二乙胺硫三氟化物反应，生成6-氟胆固醇。
• Orientation of Fluorinated Cholesterol in Lipid Bilayers Analyzed by ¹⁹F Tensor Calculation and Solid-State NMR
  作者：Nobuaki Matsumori、Yusuke Kasai、Tohru Oishi、Michio Murata、Kaoru Nomura

  DOI：10.1021/ja077580l

  日期：2008.4.1

  6-F-cholesterol was reported to exhibit biological and interfacial properties similar to unmodified cholesterol. We have also found that 6-F-cholesterol mimicked the cholesterol activity observed in the systems of amphotericin B and lipid rafts. However, to use 6-F-cholesterol as a molecular probe to explore molecular recognition in membranes, it is indispensable to have detailed knowledge of the dynamic and orientation properties of the molecule in membrane environments. In this paper, we present the molecular orientation of 6-F-cholesterol (30 mol %) in dimyristoylphosphatidylcholine (DMPC) bilayers revealed by combined use of F-19 chemical shift anisotropy (CSA), H-2 NMR, and C-F rotational echo double resonance (REDOR) experiments. The axis of rotation of 6-F-cholesterol was shown to be in a similar direction to that of cholesterol in DMPC bilayers, which is almost parallel to the long axis of the molecular frame. The molecular order parameter of 6-F-cholesterol was determined to be ca. 0.85, which is within the range of reported values of cholesterol. These findings suggest that the dynamic properties of 6-F-cholesterol in DMPC are quite similar to those of unmodified cholesterol; therefore, the introduction of a fluorine atom at C6 has virtually no effect on cholesterol dynamics in membranes. In addition, this study demonstrates the practical utility of theoretical calculations for determining the F-19 CSA principal axes, which would be extremely difficult to obtain experimentally. The combined use of quantum calculations and solid-state F-19 NMR will make it possible to apply the orientation information of F-19 CSA tensors to membrane systems.
• US4212815A
  申请人：——

  公开号：US4212815A

  公开（公告）日：1980-07-15