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)ethyl 4-methylbenzenesulfonate | 1426537-74-7

• 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)ethyl 4-methylbenzenesulfonate
• 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]ethyl 4-methylbenzenesulfonate
• CAS: 1426537-74-7
• 化学式: C₂₆H₂₈O₇S
• 分子量: 484.57
• InChiKey: DEBGMQWTRAXICP-WVQWTBLQSA-N

物化性质

• 熔点：
  119-120 °C(Solvent: Diethyl ether)
• 沸点：
  638.9±55.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

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)ethyl 4-methylbenzenesulfonate 在 盐酸 、 水 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 43.5h， 生成 (4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanoisothiochromeno[5,4a-b]benzofuran-7(7aH)-one
  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 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 98.0h， 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)ethyl 4-methylbenzenesulfonate
  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.