benzoic acid-(5α-ergostadien-(7.22t)-yl-(3β)-ester) | 4356-17-6

• 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: benzoic acid-(5α-ergostadien-(7.22t)-yl-(3β)-ester)
• 英文别名: Benzoesaeure-(5α-ergostadien-(7.22t)-yl-(3β)-ester)
• CAS: 4356-17-6
• 化学式: C₃₅H₅₀O₂
• 分子量: 502.781
• InChiKey: CBIVHLAKOSYDMO-PDMYVGQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.28
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  benzoic acid-(5α-ergostadien-(7.22t)-yl-(3β)-ester) 在 chromium(VI) oxide 、 sodium tetrahydroborate 、 selenium(IV) oxide 、 水 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Regioselective synthesis of .DELTA.6-, .DELTA.7-, and .DELTA.8-14.alpha.-cyanosterol derivatives: versatile precursors to 14.alpha.-demethylase inhibitors

  摘要：

  The efficient preparation of 3-beta-(benzoyloxy)-4,4-dimethyl-5-alpha-cholest-8(14)-en-7-one (4a) and 3-beta-benyloxy)-5-alpha-ergost-8(14)-en-7-one (4b) and their conversion to DELTA-6-, DELTA-7- or DELTA-8-14-alpha-functionalized sterols is reported. The alkylaluminum-mediated 1,4-addition of HCN (Nagata reaction) to enones 4a,b is used to introduce the 14-alpha-substituent. Reduction of these conjugate addition products (5a,b) affords the 7-alpha-hydroxysterols (6a,b). The dehydration of 6a with Martin sulfurane reagent regioselectively produces the DELTA-6-14-alpha-cyanosterol 8. Alternatively, mesylation of 6a and elimination affords a mixture of DELTA-7:DELTA-6-sterols (3:1) from which the DELTA-6-sterol is removed by selective ozonolytic degradation. The ozonolytic stability of the DELTA-7-14-alpha-cyanosterols is also exploited in the preparation of 14-alpha-cyanosterols possessing modified side chains. Ozonolysis of 3-beta-(benzoyloxy)-5-alpha-ergost-7,22-diene-14-alpha-carbonitrile (9b) gave 18, which is used to prepare compounds containing the "24 methenyl" (21) and "lanosterol" (23) side chains. The trapping of the intermediate aluminum enolate formed in the hydrocyanation of 4a gives an 8-beta-bromosterol 13. Dehydrobromination of 13 provides a novel regioselective synthesis of the difficult to prepare DELTA-8-14-alpha-functionalized sterol 14.

  DOI：

  10.1021/jo00038a024
• 作为产物：
  描述：

  麦角固醇 在 吡啶 、 镍 作用下， 生成 benzoic acid-(5α-ergostadien-(7.22t)-yl-(3β)-ester)
  参考文献：
  名称：

  Laucht, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1937, vol. 246, p. 171,174

  摘要：

  DOI：

文献信息

• The action of bromine on Δ7-ergostene and choletene derivatives
  作者：C.F. Hammer、Robert Stevenson

  DOI：10.1016/0039-128x(65)90157-1

  日期：1965.5

  Abstract The major product, obtained in yields up to 50% from the action of bromine on 5-dihydroergosteryl acetate (ergosta-7,22-dien-38-yl acetate) is 7,11,22a,23a-tetrabromoergost-8-en-38-yl acetate. It is accompanied by an isomer, 7,8,22a,23a-tetrabromoergost-14-enyl and other Δ 7,22 -ergostadienyl esters in described. Nuclear magnetic resonance chemical shifts of the angular methyl group protons

  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。
• 271. The application of the method of molecular rotation differences to steroids. Part V. Olefinic unsaturation at the 7 : 8-position
  作者：D. H. R. Barton、J. D. Cox

  DOI：10.1039/jr9480001354

  日期：——
• An Efficient, Stereocontrolled Synthesis of the 25-(<i>R</i>)-Diastereomer of Dafachronic Acid A from β-Ergosterol
  作者：Simon Giroux、E. J. Corey

  DOI：10.1021/ol702936f

  日期：2008.3.1

  A direct and stereocontrolled synthesis of the 25-(R)-diastereomer of dafachronic acid A from beta-ergosterol has been developed.
• Callow, Biochemical Journal, 1931, vol. 25, p. 87,92
  作者：Callow

  DOI：——

  日期：——
• Wieland; Benend, Justus Liebigs Annalen der Chemie, 1943, vol. 554, p. 1,6
  作者：Wieland、Benend

  DOI：——

  日期：——