trispiro[3.0.0.3.2.2]tridecan-11-one | 596821-70-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trispiro[3.0.0.3.2.2]tridecan-11-one
• 英文别名: Trispiro[3.0.0.3~6~.2~5~.2~4~]tridecan-11-one；trispiro[3.0.0.36.25.24]tridecan-11-one
• CAS: 596821-70-4
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: JQTDMPCLEHUBIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-cyclobutylidenespiro<3.3>heptane 、 三氯乙酰氯 在 锌 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成 trispiro[3.0.0.3.2.2]tridecan-11-one 、 trispiro[3.0.0.3.2.2]tridecan-10-one
  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

文献信息

• Helical primary structures of four-membered rings: (M)-trispiro[3.0.0.3.2.2]tridecane
  作者：Lutz Fitjer、Ralf Gerke、Jörg Weiser、Gabor Bunkoczi、Judit E Debreczeni

  DOI：10.1016/s0040-4020(03)00617-3

  日期：2003.6

  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.