(5S,10S)-(+)-trispiro[3.0.0.3.2.2]tridecan-10-ol | 596821-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,10S)-(+)-trispiro[3.0.0.3.2.2]tridecan-10-ol
• 英文别名: (5S,10S)-trispiro[3.0.0.3.2.2]tridecan-10-ol；(5S,10S)-trispiro[3.0.0.36.25.24]tridecan-10-ol
• CAS: 596821-76-0
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: LIAXVKGALBWKSM-GWCFXTLKSA-N

物化性质

• 沸点：
  262.5±8.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5S,10S)-(+)-trispiro[3.0.0.3.2.2]tridecan-10-ol 在 氢氧化钾 、 一水合肼 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 二乙二醇 为溶剂， 反应 3.0h， 生成 (M)-(-)-trispiro[3.0.0.3.2.2]tridecane
  参考文献：
  名称：

  Helical primary structures of four-membered rings: (M)-trispiro[3.0.0.3.2.2]tridecane

  摘要：

  The synthesis of (NI)-trispiro[3.0.0.3.2.2]tridecane [(M)-4], the first hydrocarbon with a helical primary structure of four-membered rings, is described. Key step is the kinetic resolution of a cyclobutanone through reduction with bakers' yeast. As compared to its analogue of three-membered rings, (M)-trispiro[2.0.0.2.1.1]nonane [(M)-1], the specific rotation of (M)-4 is cut in three. According to molecular mechanics calculations this could be due to a potential to adopt different conformations, not given in (M)-1, and to the fact, that (M)-4 describes a distinctly shorter section of a helix than (M)-1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00617-3
• 作为产物：
  描述：

  cyclobutyl(piperidin-1-yl)methanone 在 2,4,6-三甲基吡啶 、 三氟甲磺酸酐 、 (-)-diisopinocamphenylborane chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 26.75h， 生成 (5S,10S)-(+)-trispiro[3.0.0.3.2.2]tridecan-10-ol
  参考文献：
  名称：

  A new approach to helical primary structures of four-membered rings: (P)- and (M)-tetraspiro[3.0.0.0.3.2.2.2]hexadecane

  摘要：

  A new approach to helical primary structures of four-membered rings uses a cycloaddition of a trimethylenketeniminium salt to suitable tailored methylenecyclobutanes to assemble the desired carbon framework. The results are short and effective syntheses of (M)-trispiro[3.0.0.3.2.2]tridecane [(M-5], and (P)- and (M)-tetraspiro[3.0.0.0.3.2.2.2]hexadecane [(P)- and (M)-24]. Unlike helices of three-membered rings, the specific rotation decreases, as the length of the helix increases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.081