3β-acetoxy-19-nor-ergosta-5,7,9,22t-tetraene | 32277-79-5

• 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-19-nor-ergosta-5,7,9,22t-tetraene
• 英文别名: 3β-Acetoxy-19-nor-ergosta-5,7,9,22t-tetraen；(19-Nor-ergostatetraen-(5.7.9.22t)-yl-(3β))-acetat；O-Acetyl-neoergosterin；3β-Acetoxy-19-nor-ergostatetraen-(B.22t)；(13R)-3c-Acetoxy-13r-methyl-17c-((1R:4R)-1.4.5-trimethyl-hexen-(2t)-yl)-(14tH)-2.3.4.11.12.13.14.15.16.17-decahydro-1H-cyclopenta[a]phenanthren；3β-Acetoxy-24β_F-methyl-19-nor-cholestatetraen-(5.7.9.22t)；Essigsaeure-(19-nor-ergostatetraen-(5.7.9.22t)-yl-(3β)-ester)；19-Norergosta-5,7,9,22-tetraen-3beta-ol, acetate；[(3S,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-13-methyl-1,2,3,4,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 32277-79-5
• 化学式: C₂₉H₄₂O₂
• 分子量: 422.651
• InChiKey: VRCUACNUYFJWNN-RIWFWMEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 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-acetoxy-19-nor-ergosta-5,7,9,22t-tetraene 在 platinum(IV) oxide chromium(VI) oxide 、 盐酸 、 氢氧化钾 、 高氯酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 、 丙酮 为溶剂， 生成 3-Methoxy-19-nor-Δ^3.5.7.9,10-ergostatetraen
  参考文献：
  名称：

  类固醇研究。第LXXVII部分。22,23-二氢麦角甾醇（3β-hydroxy-19-norergosta-5,7,9-triene）的衍生物

  摘要：

  小心地氧化22,23-二氢麦角甾醇会生成3-酮和3,4-癸二酸。酮的性质是取代的β-四氢萘酮所期望的性质：例如，溴化可生成萘酚系统。二氢麦角固醇的3β-羟基很容易通过氢解作用除去。乙酸二氢麦角甾醇酯的氧化得到11-酮衍生物。

  DOI：

  10.1039/j39670001238
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 溶剂黄146 、 锌 作用下， 生成 3β-acetoxy-19-nor-ergosta-5,7,9,22t-tetraene
  参考文献：
  名称：

  The impact of aluminium on the distribution of cell wall glycoproteins of pea root tip and their Al-binding capacity

  摘要：

  Pea (Pisum sativum L.) roots were exposed to various concentrations of Al and cell wall glycoproteins containing salt-extractable proteins, SDS-extractable proteins, covalently bound proteins (CBPs), and extensins were separately extracted. The changes in their levels and the amount of bound Al to glycoproteins upon Al stress were investigated. The content of CBPs, but not of others, increased significantly with the increase of Al levels. Extensins and the salt-extractable proteins, but not the others, exhibited a marked Al-binding capacity in vivo. The amount of Al bound to extensions in vivo and in vitro was highest among the glycoproteins. The high Al-binding capacity of extensins might be caused by the high content of the hydroxy groups in hydroxyproline of extensins and Al-binding capacity to glycoproteins in the root tips may be involved in the Al-binding response in the apoplast.

  DOI：

  10.1080/00380768.2001.10408426

文献信息

• 19-Norsteroids of Unnatural Configuration from Ergosterol
  作者：Ahmed H. Eimasry、Ole Gisvold

  DOI：10.1002/jps.2600590403

  日期：1970.4

  of unnatural configuration from ergosterol has been described. This method led to the preparation of 5α,8α,9α,10α-19-norpregnan-3,20-dione which possesses unnatural configuration at positions 8 and 10. The following reaction sequence was utilized to prepare this steroid. Ergosterol was photo-oxidized to give bisergostatrienol that was pyrolyzed to yield neoergosterol whose side chain was cleaved by

  已经描述了一种由麦角固醇制备具有非天然构型的19-降冰片甾体的新方法。该方法导致制备在位置8和10具有非天然构型的5α，8α，9α，10α-19-去甲泼尼松-3，20-二酮。利用以下反应序列制备该类固醇。麦角固醇被光氧化以得到比麦角固醇，其被热解以产生新麦角固醇，其新的侧链通过臭氧分解被裂解，从而产生3β-羟基-19-norpregna-5,7,9（10）-20α-醛。第一次以结晶状态获得的醛通过3β-羟基-20-吗啉代-亚甲基-19-norpregna-5,7,9（10）-三烯衍生物的臭氧分解而降解，得到3β-羟基- 19-norpregna-5,7,9（10）-triene-20-one。后者用Ru /碳还原为相应的二醇，并且其环B又用Rh /氧化铝作为催化剂在环己烷中成功氢化。用琼斯试剂将二醇氧化为二酮。尽管以前已经记录了上述某些转化，但该报告描述了大多数中间体的技术和收率上的显着改进。
• Über die Spaltung der Doppelbindung im Neoergosterol
  作者：W. E. Bachmann、M. P. Cava、André S. Dreiding

  DOI：10.1002/hlca.19590420607

  日期：——

  By a careful sidechain cleavage of neoergosteryl acetate, 3,β-hydroxy-ar, B-bisnorcholanaldehyde could be isolated as its crystalline dimethyl acetal (Va). Acetylation and bromination afforded 3β-acetoxy-20-bromo-ar, B-bisnorcholanaldehyde(VI), which was converted to the 2,4-dinitrophenylhydrazone of 3β-acetoxy-ar, B-Δ17:20-bisnorcholenaldehyde (VII).

  通过neoergosteryl酯，3，β羟基的仔细侧链裂解AR，B-bisnorcholanaldehyde可以分离为它的结晶二甲基乙缩醛（Va）的。乙酰化和溴化，得到3β-乙酰氧基-20-溴- AR，B-bisnorcholanaldehyde（VI），将其转化为3β乙酰氧基的2,4二硝基苯肼AR，B-Δ17：20-bisnorcholenaldehyde（VII）。
• Inhoffen, Justus Liebigs Annalen der Chemie, 1932, vol. 497, p. 130,137
  作者：Inhoffen

  DOI：——

  日期：——
• The Oxidative Degradation of Neoergosteryl Acetate^*
  作者：Robert P. Jacobsen

  DOI：10.1021/ja01250a001

  日期：1943.10
• Phycomysterols and Other Sterols from the Fungus <i>Phycomyces blakesleeanus</i>
  作者：Alejandro F. Barrero、J. Enrique Oltra、Juan A. Poyatos、David Jiménez、Eulalia Oliver

  DOI：10.1021/np980199h

  日期：1998.12.1

  In the search for novel bioactive products from filamentous fungi, sterols and triterpenoids found in Phycomyces blakesleeanus were analyzed using semipreparative HPLC, CC-MS, and NMR techniques. Structures proposed for the three new compounds identified, phycomysterol A (1), phycomysterol B (2), and neoergosterol (3), were confirmed by chemical synthesis. Phycomysterols possess a new natural 19-norergostane skeleton with an aromatic B ring. Phycomysterol A showed anti-HIV activity.