(1S,3aS,7aR)-3a-hydroxy-7a-methylspiro[1,2,3,4,6,7-hexahydroindene-5,2'-1,3-dithiane]-1-carbaldehyde | 162240-25-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (1S,3aS,7aR)-3a-hydroxy-7a-methylspiro[1,2,3,4,6,7-hexahydroindene-5,2'-1,3-dithiane]-1-carbaldehyde
• CAS: 162240-25-7
• 化学式: C₁₄H₂₂O₂S₂
• 分子量: 286.459
• InChiKey: YGJRVMGGDPDHKX-UPJWGTAASA-N

物化性质

• 沸点：
  439.5±45.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3aS,7aR)-3a-hydroxy-7a-methylspiro[1,2,3,4,6,7-hexahydroindene-5,2'-1,3-dithiane]-1-carbaldehyde 在 三氟化硼乙醚 、 水 、 mercury(II) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以76%的产率得到(1S,3aS,7aR)-3a-hydroxy-7a-methyl-5-oxo-1,2,3,4,6,7-hexahydroindene-1-carbaldehyde
  参考文献：
  名称：

  Synthesis and inotropic activity of hydroindene derivatives

  摘要：

  A synthetic approach to hydroindenic inotropic agents has been developed, starting from enantiopure Hajos-Parrish (1), Hajos-Wiechert (2), and related diketones. Their transformation: into C-l formyl derivatives and other subsequent synthetic targets is described. The results of the thermodynamic equilibration between both epimers of each formyl derivative are analysed. The inotropic activities of selected compounds on right and left atrial preparations are also evaluated and discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00251-5
• 作为产物：
  描述：

  (1R,3aS,7aR)-3a-hydroxy-7a-methylspiro[1,2,3,4,6,7-hexahydroindene-5,2'-1,3-dithiane]-1-carbaldehyde 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以90%的产率得到(1S,3aS,7aR)-3a-hydroxy-7a-methylspiro[1,2,3,4,6,7-hexahydroindene-5,2'-1,3-dithiane]-1-carbaldehyde
  参考文献：
  名称：

  Stereochemical control of perhydroindanes for the synthesis of cardenolide analogs

  摘要：

  The control of the stereochemistry at C-1 of cis-perhydroindane compounds, required for the synthesis of cardenolide analogs, has been achieved by epimerization of the dithiane derivative at C-5. Molecular modeling of this kind of compounds predicted the higher stability of the C-1-beta-epimer in this and other derivatives, instead of the usually more stable C-1-alpha-epimer in the natural cardenolides and other calculated compounds.

  DOI：

  10.1016/s0040-4039(00)78471-1

文献信息

• Medarde, Manuel; Caballero, Esther; Tome, Fernando, Anales de Quimica, 1995, vol. 91, # 1-2, p. 89 - 94
  作者：Medarde, Manuel、Caballero, Esther、Tome, Fernando、Melero, Concepcion P.、Boya, Melchor、Feliciano, Arturo San

  DOI：——

  日期：——
• Hydroindenic-guanylhydrazones. Synthesis and evaluation as inotropic agents
  作者：Concepción P. Melero、Luis G. Sevillano、Esther Caballero、Fernando Tomé、Rosalía Carrón、M.José Montero、Arturo San Feliciano、Manuel Medarde

  DOI：10.1016/s0960-894x(98)00581-2

  日期：1998.11

  The synthesis and inotropic activity of two families of hydroindenic compounds are described. Among them, a bis-guanylhydrazone derivative has demonstrated to produce an interesting positive inotropic effect on guinea pig atria, displaying at higher dosis a similar effect to that elicited by digoxin. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis and inotropic activity of hydroindene derivatives
  作者：Luis G. Sevillano、Concepción P. Melero、Melchor Boya、Jose Luis López、Fernando Tomé、Esther Caballero、Rosalı́a Carrón、M. José Montero、Manuel Medarde、Arturo San Feliciano

  DOI：10.1016/s0968-0896(99)00251-5

  日期：1999.12

  A synthetic approach to hydroindenic inotropic agents has been developed, starting from enantiopure Hajos-Parrish (1), Hajos-Wiechert (2), and related diketones. Their transformation: into C-l formyl derivatives and other subsequent synthetic targets is described. The results of the thermodynamic equilibration between both epimers of each formyl derivative are analysed. The inotropic activities of selected compounds on right and left atrial preparations are also evaluated and discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Stereochemical control of perhydroindanes for the synthesis of cardenolide analogs
  作者：Manuel Medarde、Fernando Tomé、Jose Luis López、Esther Caballero、Melchor Boya、Concepción P. Melero、Arturo San Feliciano

  DOI：10.1016/s0040-4039(00)78471-1

  日期：1994.11

  The control of the stereochemistry at C-1 of cis-perhydroindane compounds, required for the synthesis of cardenolide analogs, has been achieved by epimerization of the dithiane derivative at C-5. Molecular modeling of this kind of compounds predicted the higher stability of the C-1-beta-epimer in this and other derivatives, instead of the usually more stable C-1-alpha-epimer in the natural cardenolides and other calculated compounds.