spiropentanol | 68423-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: spiropentanol
• 英文别名: Spiropentenal；Spiro[2.2]pentan-1-ol；spiro[2.2]pentan-2-ol
• CAS: 68423-22-3
• 化学式: C₅H₈O
• 分子量: 84.1179
• InChiKey: HBFGZNAONBKOIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  三氟甲磺酸酐 、 spiropentanol 在 吡啶 作用下， 生成 trifluoromethanesulfonyloxy-spiro[2.2]pentane
  参考文献：
  名称：

  Spiropentyl cations formed by solvolysis reactions

  摘要：

  DOI：

  10.1021/jo01317a002
• 作为产物：
  描述：

  2-Chlorethoxyspiropentan 在 苯基锂 作用下， 生成 spiropentanol
  参考文献：
  名称：

  Spiropentyl cations formed by solvolysis reactions

  摘要：

  DOI：

  10.1021/jo01317a002

文献信息

• Stereochemistry of the Deamination of Spiropentylamine
  作者：Kenneth B. Wiberg、Carmen Österle

  DOI：10.1021/jo990654u

  日期：1999.10.1

  The stereochemistry of the deamination of (-)-spiropentylamine in acetic acid has been studied, and it was found that one of the major products, (-)-spiropentyl acetate, was formed with essentially complete inversion of configuration. This suggests that it is formed via an S(N)2 displacement on the spiropentyldiazonium ion. The stereochemistry was established by the conversion of(-)-spiropentanecarboxylic acid to (-)-spiropentylamine via a Curtius rearrangement that proceeds with retention of configuration. The (-) acid also was converted to spiropentyl methyl ketone with methyllithium and then to (+)-spiropentyl acetate via the Baeyer-Villiger reaction that also results in retention of configuration. The deamination of N-nitroso-N-spiropentyl urea was studied in methanol, and spiropentyl methyl ether was a major product. Similarly, the reaction in water led to spiropentanol. The latter reactions also lead to 2-methoxymethyl- or 2-hydroxymethyl-1,3-butadiene, respectively, corresponding to the alternative mode of reaction via a cyclopropyl cation-allyl cation rearrangement.