3β-acetoxy-Δ⁵-cholenic aldehyde | 86476-29-1

• 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-Δ⁵-cholenic aldehyde
• 英文别名: 3β-acetoxychol-5-en-24-al；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-5-oxopentan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 86476-29-1
• 化学式: C₂₆H₄₀O₃
• 分子量: 400.602
• InChiKey: LJAJYRFZXQGURB-ISLLTSAGSA-N

物化性质

• 熔点：
  148-152 °C
• 沸点：
  490.7±28.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-Δ⁵-cholenic aldehyde 在 sodium hydroxide 、 铬酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.17h， 生成 3B-羟基-D5-胆烯酸
  参考文献：
  名称：

  由20-酮戊烷有效合成胆酸

  摘要：

  的3β羟基5α-胆烷酸（一种有效的合成8）和3β-羟基Δ 5 -cholanic酸（16）进行从5α-dihydropregnenolene（起始1）和孕烯醇酮（9）。将1和9与3,3-乙二氧基丙基溴化镁的格利雅（Grignard）反应制备，然后进行乙酰化制备的单乙酸盐（3和11）选择性脱水，得到Δ20（22）-化合物（4和12），将其氢化后再酸处理和琼斯氧化生成8和16， 分别。

  DOI：

  10.1016/0040-4020(82)80080-x
• 作为产物：
  描述：

  (3β)-3-(acetyloxy)chol-5-en-24-oyl chloride 在 吡啶 、 镍 、 丙酮 、 苯 作用下， 生成 3β-acetoxy-Δ⁵-cholenic aldehyde
  参考文献：
  名称：

  类固醇酸及其转化产物；对3β-羟基-5-胆酸和-bisnor-5-胆酸的硫醇酯进行脱硫。

  摘要：

  DOI：

  10.1021/ja01189a036

文献信息

• Asymmetric isopropylation of steroidal 24-aldehydes for the synthesis of 24(R)-hydroxycholesterol
  作者：Makoto Okamoto、Masayasu Tabe、Takao Fujii、Toshio Tanaka

  DOI：10.1016/0957-4166(95)00073-x

  日期：1995.3

  The chiral beta-amino alcohols-catalyzed addition of diisopropylzinc to steroidal 24-aldehydes successfully provided 24(R)-hydroxycholesterols in good yields with high diastereoselectivities, which are synthetic intermediates of 1 alpha,24(R)-dihydroxyvitamin D-3 (1). alpha,beta-Unsaturated steroidal aldehydes were found to give the corresponding isopropylated adducts in much higher yields (up to 91%) than those of saturated steroidal aldehydes.
• SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents
  作者：Federica Gigante、Marcel Kaiser、Reto Brun、Ian H. Gilbert

  DOI：10.1016/j.bmc.2009.06.062

  日期：2009.8

  There is an urgent need for the development of new drugs for the treatment of neglected tropical diseases such as human African trypanosomiasis, Chagas disease and leishmaniasis. Azasterols, have been shown to have activity against the parasites which cause these diseases. In this paper we report synthesis of new azasterols and subsequent analysis of the SAR. The chemistry focused on variations in the ester at the 3 beta-position of the sterol and the position of the nitrogen in the side chain. The data allowed us to derive preliminary pharmacophore models for the activity of the azasterols against the parasites which cause these diseases. (C) 2009 Elsevier Ltd. All rights reserved.
• Oxazaborolidine-Catalyzed Enantioselective Reduction of α-Methylene Ketones to Allylic Alcohols
  作者：Jun-ichi Matsuo、Takaaki Kozai、Osamu Nishikawa、Yu Hattori、Hiroyuki Ishibashi

  DOI：10.1021/jo8011013

  日期：2008.9.1

  Oxazaborolidine-catalyzed enantioselective reduction of a-methylene ketones was efficiently carried out by using borane-diethylaniline as a stoichiometric reducing agent. The combination of this method and subsequent hydrogenation of thus-formed allylic alcohol improved stereoselectivity in the reduction of 24-oxocholesteryl ester to 24-(R)-hydroxycholesteryl ester.
• Efficient, Stereoselective Synthesis of 24(<i>S</i>),25-Epoxycholesterol
  作者：Nicholas C. O. Tomkinson、Timothy M. Willson、Jonathon S. Russel、Thomas A. Spencer

  DOI：10.1021/jo981753v

  日期：1998.12.1

  Efficient, stereoselective syntheses of 24(S),25-epoxycholesterol (1) have been developed starting from cholenic acid (4) or stigmasterol (8), both featuring as the key step Sharpless asymmetric dihydroxylation of desmosterol acetate (2). This work permits preparation of gram quantities of 1 for further evaluation as a natural regulator of cholesterol metabolism, specifically, e.g., as a ligand for the LXR alpha nuclear receptor.
• Sprayer
  申请人：VINCENT SANTARELLI

  公开号：US02594223A1

  公开（公告）日：1952-04-22