(1S,3aS,7aR)-1-(hydroxymethyl)-7a-methylhexahydrospiro[indene-5,2'-[1,3]dithian]-3a(4H)-ol | 162240-24-6

• 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)-1-(hydroxymethyl)-7a-methylhexahydrospiro[indene-5,2'-[1,3]dithian]-3a(4H)-ol
• CAS: 162240-24-6
• 化学式: C₁₄H₂₄O₂S₂
• 分子量: 288.475
• InChiKey: LSCHJQLVGPUFJO-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,3aS,7aR)-1-(hydroxymethyl)-7a-methylhexahydrospiro[indene-5,2'-[1,3]dithian]-3a(4H)-ol 在 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 生成 (1S,3aS,7aR)-1-hydroxymethyl-3a-hydroxy-7a-methyl-5-perhydroindenone
  参考文献：
  名称：

  Medarde, Manuel; Caballero, Esther; Tome, Fernando, Anales de Quimica, 1995, vol. 91, # 1-2, p. 89 - 94

  摘要：

  DOI：
• 作为产物：
  描述：

  (3'aS,7'aR)-7'a-methyl-1'-methylidenespiro[1,3-dithiane-2,5'-3,4,6,7-tetrahydro-2H-indene]-3'a-ol 在 硼烷 、 hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到(1S,3aS,7aR)-1-(hydroxymethyl)-7a-methylhexahydrospiro[indene-5,2'-[1,3]dithian]-3a(4H)-ol
  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：——
• 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.