(22R,23R,24R)-22,23-dihydroxy-24-methyl-5α-cholest-2-en-6-ne | 134624-50-3

• 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: (22R,23R,24R)-22,23-dihydroxy-24-methyl-5α-cholest-2-en-6-ne
• 英文别名: (22R,23R,24R)-22,23-dihydroxy-24-methyl-5α-cholest-2-en-6-one；(5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R,5R)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-1,4,5,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one
• CAS: 134624-50-3
• 化学式: C₂₈H₄₆O₃
• 分子量: 430.671
• InChiKey: MJVCJGGOYKSADY-OKGIPSMLSA-N

物化性质

• 熔点：
  166-168 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• 沸点：
  550.0±35.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (22R,23R,24R)-22,23-dihydroxy-24-methyl-5α-cholest-2-en-6-ne 在 四氧化锇 、 硫酸 、 sodium sulfite 作用下， 生成 (2R,3S,5S,8R,9R,10R,13S,14S,17R)-17-[(2S,3R,4R,5R)-3,4-二羟基-5,6-二甲基庚烷-2-基]-2,3-二羟基-10,13-二甲基-1,2,3,4,5,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-6-酮
  参考文献：
  名称：

  Khripach, V. A.; Zhabinskii, V. N.; Ol'khovik, V. K., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 9.2, p. 1699 - 1706

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二甲基-1-丁烯 在 吡啶 、 potassium osmate(VI) dihydrate 、 sodium sulfite 、 1,4-bis-(9-O-dihydroquinidinyl)phthalazine 、 正丁基锂 、 硼烷四氢呋喃络合物 、 甲基磺酰胺 、 双氧水 、 sodium methylate 、 吡啶溴化氢盐 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 溶剂黄146 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基乙酰胺 、 水 、 叔丁醇 为溶剂， 反应 462.17h， 生成 (22R,23R,24R)-22,23-dihydroxy-24-methyl-5α-cholest-2-en-6-ne
  参考文献：
  名称：

  Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells

  摘要：

  The convergent synthesis of biosynthetic precursors of brassinosteroids with a Delta(2)-bond in cycle A-secasterol and 24-episecasterol-was performed. The key stages in the construction of the side chain in these compounds were the Julia olefination of the steroid 22-aldehyde followed by the Sharpless asymmetric dihydroxylation of the intermediate Delta(22)-olefin. The cytotoxicity of the synthesized compounds for breast carcinoma MCF-7 cells was assessed.

  DOI：

  10.1134/s1068162010060117

文献信息

• Synthesis of ergostane-type brassinosteroids with modifications in ring A
  作者：Vladimir N Zhabinskii、Darya A Osiyuk、Yuri V Ermolovich、Natalia M Chaschina、Tatsiana S Dalidovich、Miroslav Strnad、Vladimir A Khripach

  DOI：10.3762/bjoc.13.229

  日期：——

  Herein, we present a new strategy for the preparation of a broad range of brassinosteroid biosynthetic precursors/metabolites differing by the ring A fragment. The protocol is based on the use of readily available phytohormones of this class bearing a 2α,3α-diol moiety (epibrassinolide or epicastasterone) as starting materials. The required functionalities (Δ²-, 2α,3α- and 2β,3β-epoxy-, 2α,3β-, 2β,3α-, and 2β,3β-dihydroxy-, 3-keto-, 3α- and 3β-hydroxy-, 2α-hydroxy-3-keto-) were synthesized from 2α,3α-diols in a few simple steps (Corey–Winter reaction, epoxidation, oxidation, hydride reduction, etc.).

  在此，我们提出了一种新的策略，用于制备一系列不同环A片段的植物甾醇生物合成前体/代谢物。该方案基于使用易得的植物激素（具有2α,3α-二醇基团的表油菜素或表油脂酮）作为起始材料。所需的官能团（Δ2-，2α,3α-和2β,3β-环氧基，2α,3β-，2β,3α-和2β,3β-二羟基，3-酮基，3α-和3β-羟基，2α-羟基-3-酮基）可以从2α,3α-二醇中通过几个简单步骤合成（Corey-Winter反应，环氧化，氧化，氢化还原等）。
• Voigt, Brunhilde; Takatsuto, Suguru; Yokota, Takao, Journal of the Chemical Society. Perkin transactions I, 1995, # 12, p. 1495 - 1498
  作者：Voigt, Brunhilde、Takatsuto, Suguru、Yokota, Takao、Adam, Guenter

  DOI：——

  日期：——
• Configurational assignment of brassinosteroid sidechain by exciton coupled circular dichroic spectroscopy
  作者：Akira Kawamura、Nina Berova、Koji Nakanishi、Brunhilde Voigt、Günter Adam

  DOI：10.1016/s0040-4020(97)00709-6

  日期：1997.9

  A microscale method was developed to determine the sidechain configuration of brassinosteroids, a class of potent plant growth promoters. Microscale naphthoylation followed by circular dichroic (CD) spectroscopy measurement in acetonitrile unambiguously differentiate between the two possible vicinal syn-diol configurations, (22R,23R) and (22S,23S). (C) 1997 Elsevier Science Ltd.
• XRIPACH, V. A.;ZHABINSKIJ, V. N.;OLXOVIK, V. K.;LAXVICH, F. A., ZH. ORGAN. XIMII, 26,(1990) N, S. 1966-1976
  作者：XRIPACH, V. A.、ZHABINSKIJ, V. N.、OLXOVIK, V. K.、LAXVICH, F. A.

  DOI：——

  日期：——
• Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells
  作者：V. A. Khripach、V. N. Zhabinskii、O. V. Gulyakevich、O. V. Konstantinova、A. Yu. Misharin、A. R. Mekhtiev、V. P. Timofeev、Ya. V. Tkachev

  DOI：10.1134/s1068162010060117

  日期：2010.11

  The convergent synthesis of biosynthetic precursors of brassinosteroids with a Delta(2)-bond in cycle A-secasterol and 24-episecasterol-was performed. The key stages in the construction of the side chain in these compounds were the Julia olefination of the steroid 22-aldehyde followed by the Sharpless asymmetric dihydroxylation of the intermediate Delta(22)-olefin. The cytotoxicity of the synthesized compounds for breast carcinoma MCF-7 cells was assessed.