2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-ethanethiol | 1426537-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-ethanethiol
• 英文别名: 2-[(8'S,12'R,13'S)-2'-methoxyspiro[1,3-dioxolane-2,11'-15-oxatetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),6-tetraene]-13'-yl]ethanethiol
• CAS: 1426537-76-9
• 化学式: C₁₉H₂₂O₄S
• 分子量: 346.447
• InChiKey: UCNJRWTUJZZCEO-XWIAVFTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-ethanethiol 以 苯 为溶剂， 反应 36.0h， 以9 mg的产率得到(4R,4aR,7aR,12bS)-9-methoxy-2,4,4a,5,6,7a-hexahydro-1H-spiro[4,12-methanoisothiochromeno[5,4a-b]-benzofuran-7,2′-[1,3]dioxolane]
  参考文献：
  名称：

  Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

  摘要：

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.

  DOI：

  10.1021/jo3026753
• 作为产物：
  描述：

  二氢可待因酮 在 吡啶 、 sodium tetrahydroborate 、 三甲基氯硅烷 、 双氧水 、 sodium methylate 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 104.0h， 生成 2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-ethanethiol
  参考文献：
  名称：

  Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

  摘要：

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.

  DOI：

  10.1021/jo3026753

文献信息

• Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity
  作者：Robert D. Giacometti、Jan Duchek、Lukas Werner、Afeef S. Husni、Christopher R. McCurdy、Stephen J. Cutler、D. Phillip Cox、Tomas Hudlicky

  DOI：10.1021/jo3026753

  日期：2013.4.5

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.