(5S)-5-[(2R)-2-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]propyl]-3-methylideneoxolan-2-one | 173388-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (5S)-5-[(2R)-2-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]propyl]-3-methylideneoxolan-2-one
• CAS: 173388-35-7
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: VXGJCBWCWLQWSO-HDNJJZFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-5-[(2R)-2-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]propyl]-3-methylideneoxolan-2-one 在 重铬酸吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以71%的产率得到(5S)-5-[(2R)-2-[(1R,3aR,7aR)-7a-methyl-4-oxo-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylideneoxolan-2-one
  参考文献：
  名称：

  Synthesis and biological properties of 2-methylene-19-nor-25-dehydro-1α-hydroxyvitamin D3-26,23-lactones—weak agonists

  摘要：

  In a continuing effort to explore the 2-methylene-1 alpha-hydroxy-19-norvitamin D-3 class of pharmacologically important vitamin D compounds, two novel 2-methylene-19-nor-25-dehydro-1 alpha-hydroxyvitamin D-3-26,23-lactones, GC-3 and HLV, were synthesized and biologically tested. Based on reports of similarly structured molecules, it was hypothesized that these compounds might act as antagonists, at least in vitro. The pathway designed to synthesize these compounds was based on two key steps: first, the Lythgoe-type Wittig-Horner coupling of Windaus-Grundmann-type ketone 18, with phosphine oxide 15, followed, later in the synthesis, by the Zn-mediated Reformasky-type allylation of aldehyde 20 with methylbromomethylacrylate 8. Our biological data show that neither compound has antagonistic activity but acts as weak agonists in vitro and in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.011
• 作为产物：
  描述：

  (S)-5-((R)-2-((1R,3aR,4S,7aR)-7a-methyl-4-((triethylsilyl)oxy)octahydro-1H-inden-1-yl)propyl)-3-methylenedihydrofuran-2(3H)-one 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以68%的产率得到(5S)-5-[(2R)-2-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]propyl]-3-methylideneoxolan-2-one
  参考文献：
  名称：

  Synthesis and biological properties of 2-methylene-19-nor-25-dehydro-1α-hydroxyvitamin D3-26,23-lactones—weak agonists

  摘要：

  In a continuing effort to explore the 2-methylene-1 alpha-hydroxy-19-norvitamin D-3 class of pharmacologically important vitamin D compounds, two novel 2-methylene-19-nor-25-dehydro-1 alpha-hydroxyvitamin D-3-26,23-lactones, GC-3 and HLV, were synthesized and biologically tested. Based on reports of similarly structured molecules, it was hypothesized that these compounds might act as antagonists, at least in vitro. The pathway designed to synthesize these compounds was based on two key steps: first, the Lythgoe-type Wittig-Horner coupling of Windaus-Grundmann-type ketone 18, with phosphine oxide 15, followed, later in the synthesis, by the Zn-mediated Reformasky-type allylation of aldehyde 20 with methylbromomethylacrylate 8. Our biological data show that neither compound has antagonistic activity but acts as weak agonists in vitro and in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.011