24-methylene cholesteryl acetate | 13000-50-5

• 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: 24-methylene cholesteryl acetate
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 13000-50-5
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: HDXVMNXZJASMLL-OJMNJZCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  24-methylene cholesteryl acetate 在 溶剂黄146 作用下， 生成 3β-acetoxy-cholest-5-en-24-one
  参考文献：
  名称：

  Marine Sterols. I. Isolation of 24-Methylenecholesterol from Molluscs

  摘要：

  DOI：

  10.1021/ja01620a050
• 作为产物：
  描述：

  24-oxocholesterol 在 sodium hydride 作用下， 以 1,4-二氧六环 、 吡啶 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 24-methylene cholesteryl acetate
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (V): efficient and stereospecific synthesis of 24-methylene-cholest-5-ene-3β,7α-diol and its C-7 epimer

  摘要：

  This paper describes the efficient and stereospecific synthesis of cytotoxicdihydroxylated sterols, 24-methylene-cholest-5-ene-3beta,7alpha-diol 1, and its C-7 epimer, 24-methylene-cholest-5-ene-3beta,7beta-diol 2. The crux of the synthesis is that the selective allylic oxidation of 24-methylenecholesteryl acetate proceeds to 24-niethylene-7-keto-cholesteryl acetate without extensive by product formation from reaction at the Delta24(28) double bond. This methodology may be useful for the preparation of other oxysterols with non-standard side chains. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.09.010

文献信息

• Preparative Method for the Quantitative Separation of Methylenic Sterols from Unsaturated Sterol Mixtures by Chemoselective Hydroxymercuration-Deoxymercuration
  作者：Laïla El Kihel、Georges Charles

  DOI：10.1055/s-2006-942495

  日期：2006.8

  intermediates were easily purified by flash chromatography on silica gel column and the reactive alkenes were regenerated by deoxymercuration in a biphasic system (ethyl acetate/I M HCl, 2:1 ratio). These conditions leave the ring double bonds of steroids intact. No isomerization of methylene double bonds was observed.

  报道了一种前所未有的选择性和定量方法，允许从不饱和甾醇混合物中分离亚甲基甾醇。我们已将改良布朗条件下的羟基汞化反应扩展到对三十种不饱和甾醇作为各种甾醇混合物的系统研究。在甾醇的亚甲基侧链上实现了高产的定向化学选择性羟基汞化。得到的有机汞中间体很容易通过硅胶柱上的快速色谱法纯化，反应性烯烃通过在双相系统（乙酸乙酯/1M HCl，2:1比例）中脱氧汞再生。这些条件使类固醇的环双键完好无损。没有观察到亚甲基双键的异构化。
• Investigations on the Δ23-, Δ24(28)- and Δ25-Sterols of zea mays
  作者：Neil L.A. Misso、L. John Goad

  DOI：10.1016/0031-9422(84)83081-2

  日期：1984.1

  25 -compound, cyclolaudenol, were recognized. These various Δ 23 - and Δ 25 -sterols may have some importance in alternative biosynthetic routes to the major sterols, particularly the 24β-methylcholest-5-en-3β-ol component of the C 28 -sterols. Radioactivity from both [2- 14 C]MVA and [methyl- 14 C]methionine was incorporated by Z. mays shoots into the sterol mixture. Although 24-methylene and 24-ethylidene

  摘要 用薄层色谱、高效液相色谱、气相色谱/质谱联用技术和 1 H 核磁共振技术分离并表征了玉米笋中的甾醇。总共鉴定了 22 种 4-去甲基甾醇，它们包括痕量的 Δ 23 -、Δ 24 - 和Δ 25 - 甾醇、24-甲基胆甾醇-5、E -23-dien-3β-ol、24-甲基胆甾醇- 5, Z -23-dien-3β-ol, 24-methylcholesta-5,25-dien-3β-ol, 24-ethylcholesta-5,25-dien-3β-ol 和 24-ethylcholesta-5,24-dien- 3β-醇。在 4,4-二甲基甾醇级分中，环木蒿醇和 24-亚甲基环木桐醇是主要的甾醇成分，但也发现了少量的 Δ 23 - 化合物环沙多和 Δ 25 - 化合物环月桂醇。这些不同的 Δ 23 - 和 Δ 25 - 甾醇在主要甾醇的替代生物合成途径中可能具有一定的重要性，特别是 C
• Untersuchungen uber Steroide. XXXI. Umlagerung einer Doppelbindung an C<SUB>24 (28)</SUB> der Sterin-Seitenkette bei Einwirkung von Jod.
  作者：Kiyoshi Sakai

  DOI：10.1248/cpb.11.752

  日期：——

  Es wird eine Umlagerungsreaktion der Doppelbindung an C24 (28) der Sterinseitenkette beschrieben. Die Doppelbindung an C24 (28) des Fucosterylacetates bzw. des 24-Methylencholesterylacetates laβt sich durch Einwirkung von Jod in die 24 (25)-Stellung umlagern.

  描述了固醇侧链 C24（28）位双键的重排反应。在碘的作用下，醋酸褐藻酯或醋酸 24-亚甲基胆固醇酯的 C24（28）位双键可重新排列到 24（25）位。
• Roadside Particulate Air Pollution in Bangkok
  作者：Wanida Jinsart、Kenji Tamura、Samarnchai Loetkamonwit、Sarawut Thepanondh、Kanae Karita、Eiji Yano

  DOI：10.1080/10473289.2002.10470845

  日期：2002.9

  Airborne fine particles of PM2.5-10 and PM2.5 in Bangkok, Nonthaburi, and Ayutthaya were measured from December 22, 1998, to March 26, 1999, and from November 30, 1999, to December 2, 1999. Almost all the PM10 values in the high-polluted (H) area exceeded the Thailand National Ambient Air Quality Standards (NAAQS) of 120 mug/m(3). The low-polluted (L) area showed low PM10 (34-74 mug/m(3) in the daytime and 54-89 mug/m(3) at night). PM2.5 in the H area varied between 82 and 143 mug/m(3) in the daytime and between 45 and 146 mug/m(3) at night. In the L area, PM2.5 was quite low both day and night and varied between 24 and 54 mug/m(3), lower than the U.S. Environmental Protection Agency (EPA) standard (65 mug/m(3)). The personal exposure results showed a significantly higher proportion of PM2.5 to PM10 in the H area than in the L area (H = 0.80 +/- 0.08 and L = 0.65 +/- 0.04).Roadside PM10 was measured simultaneously with the Thailand Pollution Control Department (PCD) monitoring station at the same site and at the intersections where police work. The result from dual simultaneous measurements of PM10 showed a good correlation (correlation coefficient: r = 0.93); however, PM levels near the roadside at the intersections were higher than the concentrations at the monitoring station. The relationship between ambient PM level and actual personal exposures was examined. Correlation coefficients between the general ambient outdoors and personal exposure levels were 0.92 for both PM2.5 and PM10.Bangkok air quality data for 1997-2000, including 24-hr average PM10, NO2, SO2, and O-3 from eight PCD monitoring stations, were analyzed and validated. The annual arithmetic mean PM10 of the PCD data at the roadside monitoring stations for the last 3 years decreased from 130 to 73 mug/m(3), whereas the corresponding levels at the general monitoring stations decreased from 90 to 49 mug/m(3). The proportion of days when the level of the 24-hr average PM10 exceeded the NAAQS was between 13 and 26% at roadside stations. PCD data showed PM10 was well correlated with NO2 but not with SO2, suggesting that automobile exhaust is the main source of the particulate air pollution. The results obtained from the simultaneous measurement of PM2.5 and PM10 indicate the potential environmental health hazard of fine particles. In conclusion, Bangkok traffic police were exposed to high levels of automobile-derived particulate air pollution.
• Marine Sterols. I. Isolation of 24-Methylenecholesterol from Molluscs
  作者：D. R. Idler、U. H. M. Fagerlund

  DOI：10.1021/ja01620a050

  日期：1955.8