2-[3-[3,17β-dihydroxyestra-1,3,5(10)-trien-17α-yl]-prop-2-ynyl]malonic acid, monomethyl ester | 1234701-31-5

• 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: 2-[3-[3,17β-dihydroxyestra-1,3,5(10)-trien-17α-yl]-prop-2-ynyl]malonic acid, monomethyl ester
• CAS: 1234701-31-5
• 化学式: C₂₅H₃₀O₆
• 分子量: 426.51
• InChiKey: WVQIZVBAKJSTLH-AHWVTMKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  104.06
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-[3-[3,17β-dihydroxyestra-1,3,5(10)-trien-17α-yl]-prop-2-ynyl]malonic acid, monomethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 以96%的产率得到2-[3-[3,17β-dihydroxyestra-1,3,5(10)-trien-17α-yl]-prop-2-ynyl]malonic acid
  参考文献：
  名称：

  Synthesis of 17α-substituted ethynylestradiols: Potential ligands for drug vectors

  摘要：

  17 alpha-substituted ethynylestradiols, derived from estrone, were converted to their corresponding 17 alpha-(bromo- or iodo-propargyl)estrone intermediates. Nucleophilic substitution onto these moieties with malonate diester followed by hydrolysis and complexation with cis-Pt(Me(2)en)I-2 (Me(2)en = N,N-dimethylethylenediamine) gave cis-Pt(Me(2)en)(2-(3-(17 beta-estradiol-17 alpha-yl)-prop-2-ynyl)malonato) 7, thus demonstrating that these estrogen-derived compounds can be used to synthesize stable Pt(II) complexes. The 3-(17 beta-estradiol-17 alpha-yl)-prop-2-ynyl-1-sulfanylethylthiol 23 was also prepared. Crown Copyright (C) 2010 Published by Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.03.004
• 作为产物：
  描述：

  2-[3-[3,17β-dihydroxyestra-1,3,5(10)-trien-17α-yl]-prop-2-ynyl]malonic acid dimethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 以77%的产率得到2-[3-[3,17β-dihydroxyestra-1,3,5(10)-trien-17α-yl]-prop-2-ynyl]malonic acid, monomethyl ester
  参考文献：
  名称：

  Synthesis of 17α-substituted ethynylestradiols: Potential ligands for drug vectors

  摘要：

  17 alpha-substituted ethynylestradiols, derived from estrone, were converted to their corresponding 17 alpha-(bromo- or iodo-propargyl)estrone intermediates. Nucleophilic substitution onto these moieties with malonate diester followed by hydrolysis and complexation with cis-Pt(Me(2)en)I-2 (Me(2)en = N,N-dimethylethylenediamine) gave cis-Pt(Me(2)en)(2-(3-(17 beta-estradiol-17 alpha-yl)-prop-2-ynyl)malonato) 7, thus demonstrating that these estrogen-derived compounds can be used to synthesize stable Pt(II) complexes. The 3-(17 beta-estradiol-17 alpha-yl)-prop-2-ynyl-1-sulfanylethylthiol 23 was also prepared. Crown Copyright (C) 2010 Published by Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.03.004