2-Hydroxymethylen-cholest-4-en-3-on | 2841-80-7

• 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: 2-Hydroxymethylen-cholest-4-en-3-on
• 英文别名: (8S,9S,10R,13R,14S,17R)-2-(hydroxymethylidene)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-6,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 2841-80-7
• 化学式: C₂₈H₄₄O₂
• 分子量: 412.656
• InChiKey: PFDDSGLPIFLJTA-RANCRSHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Hydroxymethylen-cholest-4-en-3-on 在 乙酸酐 作用下， 生成 A-nor-Δ³⁽⁵⁾-Cholesten-2-on
  参考文献：
  名称：

  Synthese von 5-Methyl-3-oxa-A-nor-5?-cholestan und 3-Oxa-?4-cholesten-2-on

  摘要：

  Abstract2, 3‐seco‐Δ4‐Cholestene‐2, 3‐dicarboxylic acid (5) was prepared in 30% yield from 2‐hydroxymethylene‐Δ4‐cholestene‐3‐one (1) by ozonolysis under special conditions. Pyrolysis of the pure di‐acid 5 gave A‐nor‐Δ3(5)‐cholestene‐2‐one (6), the anhydride 2 and 5‐methyl‐3‐oxa‐A‐nor‐5β‐cholestane‐2‐one (8). Pyrolysis of amorphous acidic material obtained by the ozonolysis of 1 yielded the enol‐lactones 7 and 9 as additional products. LiA1H4‐reduction of the γ‐lactone 8 gave the diol 10, which was transformed into 5‐methyl‐3‐oxa‐A‐nor‐5β‐cholestane (13) by treatment with tosyl chloride in pyridine.

  DOI：

  10.1002/hlca.19670500608
• 作为产物：
  描述：

  4-胆甾烯-3-酮 、 甲酸乙酯 在 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 生成 2-Hydroxymethylen-cholest-4-en-3-on
  参考文献：
  名称：

  Huynh,C.; Julia,S., Bulletin de la Societe Chimique de France, 1971, p. 4402 - 4407

  摘要：

  DOI：

文献信息

• Bloch,J.-C.; Ourisson,G., Bulletin de la Societe Chimique de France, 1964, p. 3011 - 3017
  作者：Bloch,J.-C.、Ourisson,G.

  DOI：——

  日期：——
• Synthesis, biological active molecular design, and molecular docking study of novel deazaflavin–cholestane hybrid compounds
  作者：Ajaya R. Shrestha、Takashi Shindo、Noriyuki Ashida、Tomohisa Nagamatsu

  DOI：10.1016/j.bmc.2008.07.089

  日期：2008.9

  Novel deazaflavin-cholestane hybrid compounds, 3',8'-disubstituted-5'-deazacholest-2,4-dieno[2,3g] pteridine-2',4'(3'H, 8'H)-diones, have been synthesized by condensation reaction between 6-(monosubstituted amino)-pyrimidin-2,4(1H,3H)-diones and 2-hydroxymethylenecholest-4-en-3-one in presence of p-toluenesulfonic acid monohydrate and diphenyl ether. The antitumor activities against human tumor cell lines (CCRF-HSB-2 and KB cells) have been investigated in vitro, and many of these compounds showed promising antitumor activities. Furthermore, molecular docking study using LigandFit within the software package Discovery Studio 1.7 was done for lead optimization of these compounds as potential PTK inhibitors. In general, all of the synthesized steroid-hybrid compounds showed good binding affinities into PTK (PDB code: 1t46). (C) 2008 Elsevier Ltd. All rights reserved.