(8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(E,1R,4R)-1,4,5-三甲基己-2-烯基]-1,2,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3-酮 | 516-77-8

• 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
• 中文名称: (8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(E,1R,4R)-1,4,5-三甲基己-2-烯基]-1,2,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3-酮
• 英文名称: ergosta-4,6,22-trien-3-one
• 英文别名: ergost-4,6,22-trien-3-one；isoergosterone；ergosta-4,6,22t-trien-3-one；Ergosta-4,6,22t-trien-3-on；Ergostatrien-(4.6.22t)-on-(3)；4,6,22-ergosta-trien-3-one；(8S,9S,10R,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 516-77-8
• 化学式: C₂₈H₄₂O
• 分子量: 394.641
• InChiKey: LJNASASDNLCNOS-ADBSWBDJSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  501.8±17.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(E,1R,4R)-1,4,5-三甲基己-2-烯基]-1,2,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3-酮 在 丙醇 、 sodium 、 乙酸乙酯 、 铂 作用下， 生成 3α-acetoxy-5β-ergost-22t-ene
  参考文献：
  名称：

  380.分子旋转差异法在类固醇上的应用。第十部分“ β-二氢麦角固醇”。

  摘要：

  DOI：

  10.1039/jr9490001771
• 作为产物：
  描述：

  3-methoxy-ergosta-3,5,7,22t-tetraene 在 盐酸 作用下， 生成 (8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(E,1R,4R)-1,4,5-三甲基己-2-烯基]-1,2,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3-酮
  参考文献：
  名称：

  A Synthesis of Progesterone from Ergosterol¹

  摘要：

  DOI：

  10.1021/ja01610a036

文献信息

• Studies on the constituents of orchidaceous plants. V Isolation, structure, and C-13 signal assignments of novel methylsterols from Nervilia purpurea Schlechter.
  作者：TOHRU KIKUCHI、SHIGETOSHI KADOTA、SATOKO MATSUDA、HISASHI SUEHARA

  DOI：10.1248/cpb.34.3183

  日期：——

  Four new methylsterols, cyclonervilasterol, 24-epicyclonervilasterol, dihydrocyclonervilasterol, and 24-epihihydrocyclonervilasterol, were isolated from the methylsterol fraction of Nervilia purpurea SCHLECHTER by reversed-phase high-performance liquid chromatography. The structures 2a, 3a, 5a, and 6a were proposed for these compounds, respectively, based on chemical evidence and two-dimensional nuclear magnetic resonance spectroscopy including INADEQUATE (Incredible Natural Abandance Double Quantum Transfer Experiment).

  从Nervilia purpurea SCHLECHTER的甲基甾醇组分中，通过反相高效液相色谱法分离出四种新的甲基甾醇，分别为环神经甾醇、24-表环神经甾醇、二氢环神经甾醇和24-表氢环神经甾醇。根据化学证据和包括INADEQUATE（不可思议的天然丰度双量子转移实验）在内的二维核磁共振光谱学，提出了对这些化合物的结构2a、3a、5a和6a的假设。
• A Convenient Synthesis of 1α-Hydroxyvitamin D₂
  作者：Yoji Tachibana

  DOI：10.1246/bcsj.61.3915

  日期：1988.11

  afforded ergosta-1,5,7,22-tetraen-3β-ol (6). The t-butyldimethylsilyl ether derivatives (8) of the Diels–Alder cyclo adduct (7) derived from 6 and 4-phenyl-3H-1,2,4-triazole-3,5-dione was oxidized with m-CPBA to the diepoxide adduct (9). The 1α,2α-epoxide of the diepoxy alcohol (10) obtained after the removal of the silyl group of 9 was selectively reduced with LiAlH4 to yield the 22,23-epoxy-1α,3β-diol (11)

  在酸性条件下用乙酸异丙烯酯处理 ergosta-1,4,6,22-tetraen-3-one (4) 的烯醇乙酰化得到 3-乙酰氧基-1,3,5,7,22-ergostapentaene (5)。5 用硼氢化钙还原得到 ergosta-1,5,7,22-tetraen-3β-ol (6)。衍生自 6 和 4-苯基-3H-1,2,4-三唑-3,5-二酮的 Diels-Alder 环加合物 (7) 的叔丁基二甲基甲硅烷基醚衍生物 (8) 用 m-CPBA 氧化成双环氧化物加合物 (9)。脱除 9 的甲硅烷基后得到的二环氧醇 (10) 的 1α,2α-环氧化物用 LiAlH4 选择性还原得到 22,23-环氧-1α,3β-二醇 (11)，随后将 11 转化到相应的二乙酸酯 (12)。用碘化钠和三氟乙酸酐的组合对 12 的 22,23-环氧化物进行脱氧，得到 1α-乙酰氧基麦角甾醇乙酸酯 (13)。
• Use of derivatives of cholest-4-en-3-one as medicaments, pharmaceutical compositions containing same, novel derivatives and preparation method thereof
  申请人：Bordet Thierry

  公开号：US20060217358A1

  公开（公告）日：2006-09-28

  Compound of formula I where X=O or ═N—OH group, R represents a group chosen from A=hydrogen or together with B a carbon-carbon bond, B=hydrogen, hydroxy or together with A a carbon-carbon bond, C, D, E, F=hydrogen or together with D a carbon-carbon bond, or the one of its addition salts with pharmaceutically acceptable acids, with the exception of a few compounds, as a medicament, use in particular as neuroprotectors, novel compounds of formula I and pharmaceutical compositions.

  化合物I的化学式如下，其中X可以是O或═N—OH基团，R代表从以下组中选择的一种：A=氢或与B一起形成碳-碳键，B=氢、羟基或与A一起形成碳-碳键，C、D、E、F=氢或与D一起形成碳-碳键，或其与药学上可接受的酸的一种或多种加成盐，除了少数化合物外，作为药物，特别是作为神经保护剂，化合物I的新型化合物和制药组合物。
• USE AS MEDICAMENTS OF DERIVATIVES OF CHOLEST-4-EN-3-ONE, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, NOVEL DERIVATIVES AND THEIR PREPARATION PROCESS
  申请人：BORDET Thierry

  公开号：US20100216752A1

  公开（公告）日：2010-08-26

  A method for providing neuroprotection to a patient in need of neuroprotection, comprising administering a neuroprotective-effective amount of a compound of formula I in which X is an oxygen atom or an ═N—OH group, R is selected from the group consisting of A is a hydrogen atom or together with B a carbon-carbon bond, B is a hydrogen atom, a hydroxy group or together with A a carbon-carbon bond, C is a hydrogen atom or together with D a carbon-carbon bond, D is a hydrogen atom or together with C a carbon-carbon bond, E is a hydrogen atom or together with F a carbon-carbon bond, F is a hydrogen atom or together with E a carbon-carbon bond, or an addition salt with a pharmaceutically acceptable acid.

  一种用于向需要神经保护的患者提供神经保护的方法，包括给予化合物I的神经保护有效量，其中X是氧原子或═N—OH基团，R选自以下组合：A是氢原子，或者与B一起形成碳-碳键，B是氢原子、羟基或者与A一起形成碳-碳键，C是氢原子，或者与D一起形成碳-碳键，D是氢原子，或者与C一起形成碳-碳键，E是氢原子，或者与F一起形成碳-碳键，F是氢原子，或者与E一起形成碳-碳键，或者与药学上可接受的酸形成加成盐。
• METHOD FOR PROVIDING NEUROPROTECTION
  申请人：Bordet Thierry

  公开号：US20120309721A1

  公开（公告）日：2012-12-06

  A method for providing neuroprotection to a patient in need of neuroprotection, comprising administering a neuroprotective-effective amount of a compound of formula I in which X is an oxygen atom or an =N—OH group, R is selected from the group consisting of A is a hydrogen atom or together with B a carbon-carbon bond, B is a hydrogen atom, a hydroxy group or together with A a carbon-carbon bond, C is a hydrogen atom or together with D a carbon-carbon bond, D is a hydrogen atom or together with C a carbon-carbon bond, E is a hydrogen atom or together with F a carbon-carbon bond, F is a hydrogen atom or together with E a carbon-carbon bond, or an addition salt with a pharmaceutically acceptable acid.

  一种为需要神经保护的患者提供神经保护的方法，包括给予化合物I的神经保护有效剂量，其中X是氧原子或=N-OH基团，R从以下组中选择：A是氢原子或与B一起形成碳-碳键，B是氢原子、羟基或与A一起形成碳-碳键，C是氢原子或与D一起形成碳-碳键，D是氢原子或与C一起形成碳-碳键，E是氢原子或与F一起形成碳-碳键，F是氢原子或与E一起形成碳-碳键，或与药学上可接受的酸形成加成盐。