(3β,22E)-ergosta-5,7,22-trien-3-ol benzoate | 5035-30-3

• 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: (3β,22E)-ergosta-5,7,22-trien-3-ol benzoate
• 英文别名: ergosterol benzoate；[(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] benzoate
• CAS: 5035-30-3
• 化学式: C₃₅H₄₈O₂
• 分子量: 500.765
• InChiKey: KTEAPQRLLFTRGZ-WKDGUCRUSA-N

物化性质

• 熔点：
  164-165 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))
• 沸点：
  582.5±49.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3β,22E)-ergosta-5,7,22-trien-3-ol benzoate 在 镍 氢气 作用下， 以 1,4-二氧六环 为溶剂， 生成 benzoic acid-(5α-ergostadien-(7.22t)-yl-(3β)-ester)
  参考文献：
  名称：

  溴对Δ7-麦角甾烯和胆甾醇衍生物的作用

  摘要：

  摘要 溴作用于乙酸 5-二氢麦角甾醇酯（ergosta-7,22-dien-38-yl acetate）的主要产物是 7,11,22a,23a-tetrabromoergost-8-en，产率高达 50%。 -38-基乙酸酯。它伴随着异构体，7,8,22a,23a-四溴麦角-14-烯基和其他描述的Δ 7,22-麦角二烯基酯。报告了代表类别的角甲基质子的核磁共振化学位移，并与计算值进行了比较。

  DOI：

  10.1016/0039-128x(65)90157-1
• 作为产物：
  描述：

  麦角固醇 、 苯甲酰氯 在 吡啶 作用下， 生成 (3β,22E)-ergosta-5,7,22-trien-3-ol benzoate
  参考文献：
  名称：

  The Role of Radial Clearance on the Performance of Foil Air Bearings

  摘要：

  Load capacity tests were conducted to determine how radial clearance variations affect the load capacity coefficient of foil air bearings. Two Generation III foil air bearings with the same design but possessing different initial radial clearances were tested at room temperature against an as-ground PS304 coated journal operating at 30000 rpm. Increases in radial clearance were accomplished by reducing the journal's outside diameter via an in-place grinding system. Front each load capacity test the bearing load capacity coefficient was calculated from the rule-of-thumb (ROT) model developed for foil air bearings.The test results indicate that, in terms of the load capacity coefficient, radial clearance has a direct impact on the performance of the foil air bearing. Each test bearing exhibited an optimum radial clearance that resulted in a maximum load capacity coefficient. Relative to this optimum value are two separate operating regimes that are governed by different modes of failure. Bearings operating with radial clearances less than the optimum exhibit load capacity coefficients that are a strong function of radial clearance and are prone to a thermal runaway failure mechanism and bearing seizure. Conversely, a bearing operating with a radial clearance m,ice the optimum suffered only a 20% decline in its maximum load capacity coefficient and did not experience any thermal management problems. However, it is unknown to what degree these changes in radial clearance had on other performance parameters, such (is the stiffness and damping properties of the bearings.

  DOI：

  10.1080/10402000208982578
• 作为试剂：
  描述：

  C₈H₁₃BrO₄ 、 苯甲酰氯 、 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 (3β,22E)-ergosta-5,7,22-trien-3-ol benzoate 作用下， 以 二氯甲烷 为溶剂， 以44 %的产率得到
  参考文献：
  名称：

  海星环类固醇苷的全合成。第 3 部分，Luzonicosides A 和 D 的正式全合成

  摘要：

  Luzonicosides A ( 1 ) 和 D ( 2 ) 是从太平洋海星Echinaster Luzonicus中分离出来的主要皂苷，具有空间拥挤的 16 元环，该环由桥接 3β,6β-二羟基-Δ 7 -ene的 C3 和 C6 形成分别通过糖苷键和醚键具有 1,2-反式连接的线性三糖的类固醇。在这里，我们描述了海星环状甾体苷1和2的正式全合成。合成路线是高度模块化和通用的，涉及通过 Au(I) 催化的分子内糖基化构建 16 元大环，高效安装不饱和糖基与邻位-hexynylbenzoates，通过后氧化精制葡萄糖醛酸单元，以及从头合成醚连接的吡喃糖单元。

  DOI：

  10.1002/cjoc.202200787

文献信息

• Improved synthesis of 1,2,4-triazoline-3,5-dione derivatives of ergosterol and a new method for their reconversion to ergosterol
  作者：Derek H.R. Barton、Xavier Lusinchi、Jesús Sandoval Ramírez

  DOI：10.1016/s0040-4039(00)88078-8

  日期：1983.1

  The ergosterol diene system reacts in excellent yield with a series of 4-substituted 1,2,4-triazoline-3,5-diones generated by in situ oxidation of the appropriate hydrazides with phenylseleninic anhydride or phenylseleninic acid. Diaryltelluroxide and diphenylselenoxide are also efficient oxdants. The diene system can be smoothly regenerated by alkaline hydrolysis.

  麦角固醇二烯系统以优异的产率与一系列的4-取代的1,2,4-三唑啉-3,5-二酮反应，所述一系列的4-取代的1,2,4-三唑啉-3,5-二酮是通过适当的酰肼与苯硒酸二酐或苯基硒酸的原位氧化而生成的。二芳基四氢呋喃和二苯硒酸也是有效的氧化剂。二烯体系可以通过碱水解而平滑地再生。
• Selective reduction of the 7(8)-double bond in ergosterol
  作者：Derek H. R. Barton、Xavier Lusinchi、L�on Magdzinski、Jesus Sandoval Ramirez

  DOI：10.1039/c39840001236

  日期：——

  Reduction of ergosterol alkoxide derivatives with lithium metal gives better yields of the 7(8)-reduced product brassicasterol than previous procedures; the mixed products of the reduction are easily converted into ergosta-2,22-dien-6-one, a convenient intermediate for brassinolide synthesis.

  用锂金属还原麦角甾醇的醇盐衍生物比以前的方法得到的7（8）还原的产物芸苔甾醇具有更好的收率。还原的混合产物很容易转化为ergosta-2,22-dien-6-one，这是油菜素内酯合成的便捷中间体。
• 158. The application of the method of molecular rotation differences to steroids. Part IV. Optical anomalies
  作者：D. H. R. Barton、J. D. Cox

  DOI：10.1039/jr9480000783

  日期：——
• Barton; Lusinchi; Sandoval Ramirez, Bulletin de la Societe Chimique de France, 1985, vol. NO. 5, # 5, p. 849 - 858
  作者：Barton、Lusinchi、Sandoval Ramirez

  DOI：——

  日期：——
• Bills; Honeywell, Journal of Biological Chemistry, 1928, vol. 80, p. 15,22
  作者：Bills、Honeywell

  DOI：——

  日期：——