cis-2-hydroxymethyl-cyclopentanecarboxylic acid hydrazide | 14668-73-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-2-hydroxymethyl-cyclopentanecarboxylic acid hydrazide
• 英文别名: cis-2-Hydroxymethyl-cyclopentan-carbonsaeure-hydrazid；(1S,2R)-2-(Hydroxymethyl)cyclopentane-1-carbohydrazide
• CAS: 14668-73-6
• 化学式: C₇H₁₄N₂O₂
• 分子量: 158.2
• InChiKey: VAPPPUPPBGBKGI-WDSKDSINSA-N

物化性质

• 沸点：
  376.6±11.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  cis-2-hydroxymethyl-cyclopentanecarboxylic acid hydrazide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 cis-N-methyl-2-hydroxymethylcyclopentylamine
  参考文献：
  名称：

  Amine Oxides. VII. The Thermal Decomposition of the N-Oxides of N-Methylazacycloalkanes^1,2

  摘要：

  Ring cleavage of the N-oxides of N-methylazacycloalkanes by a thermal elimination reaction does not occur when the ring is six-membered and becontes progressively easier as the ring size is increased from seven to eight atoms. N-Methylpiperidine oxide gave no product from a cis beta-elimination reaction, while pyrolysis of the homologous N-methylhexamethyleneimine and N-methylheptamethyleneimine oxides led to the unsaturated hydroxylamines in yields of 53 and 79%, respectively. These results support a planar five-membered transition state for the amine oxide pyrolysis. The unsaturated hydroxylamines were converted to unsaturated and saturated secondary amines. The thermal decomposition of a mixture of he cis and trans isomers of N-methyl-alpha-pipecoline oxide formed the expected N-methyl-N-5-hexenylhydroxylamine as well as a saturated bicyclic product, formulated as cis-N-methyl-3-oxa-2-azabicyclo [3.3.01 octane. A possible mechanism for the formation of this product is presented. The cis and trans isomers of N-methyl-a-pipecoline oxide have been separated and characterized. Each Of the isomers has been pyrolyzed separately and only trans-N-methyl-a-pipecoline oxide formed the expected unsaturated hydroxylamine.

  DOI：

  10.1021/ja01502a052
• 作为产物：
  描述：

  hexahydro-cyclopenta[c]furan-1-one 在 肼 作用下， 生成 cis-2-hydroxymethyl-cyclopentanecarboxylic acid hydrazide
  参考文献：
  名称：

  Amine Oxides. VII. The Thermal Decomposition of the N-Oxides of N-Methylazacycloalkanes^1,2

  摘要：

  Ring cleavage of the N-oxides of N-methylazacycloalkanes by a thermal elimination reaction does not occur when the ring is six-membered and becontes progressively easier as the ring size is increased from seven to eight atoms. N-Methylpiperidine oxide gave no product from a cis beta-elimination reaction, while pyrolysis of the homologous N-methylhexamethyleneimine and N-methylheptamethyleneimine oxides led to the unsaturated hydroxylamines in yields of 53 and 79%, respectively. These results support a planar five-membered transition state for the amine oxide pyrolysis. The unsaturated hydroxylamines were converted to unsaturated and saturated secondary amines. The thermal decomposition of a mixture of he cis and trans isomers of N-methyl-alpha-pipecoline oxide formed the expected N-methyl-N-5-hexenylhydroxylamine as well as a saturated bicyclic product, formulated as cis-N-methyl-3-oxa-2-azabicyclo [3.3.01 octane. A possible mechanism for the formation of this product is presented. The cis and trans isomers of N-methyl-a-pipecoline oxide have been separated and characterized. Each Of the isomers has been pyrolyzed separately and only trans-N-methyl-a-pipecoline oxide formed the expected unsaturated hydroxylamine.

  DOI：

  10.1021/ja01502a052

文献信息

• US6207862B1
  申请人：——

  公开号：US6207862B1

  公开（公告）日：2001-03-27
• Amine Oxides. VII. The Thermal Decomposition of the N-Oxides of N-Methylazacycloalkanes^1,2
  作者：Arthur C. Cope、Norman A. LeBel

  DOI：10.1021/ja01502a052

  日期：1960.9

  Ring cleavage of the N-oxides of N-methylazacycloalkanes by a thermal elimination reaction does not occur when the ring is six-membered and becontes progressively easier as the ring size is increased from seven to eight atoms. N-Methylpiperidine oxide gave no product from a cis beta-elimination reaction, while pyrolysis of the homologous N-methylhexamethyleneimine and N-methylheptamethyleneimine oxides led to the unsaturated hydroxylamines in yields of 53 and 79%, respectively. These results support a planar five-membered transition state for the amine oxide pyrolysis. The unsaturated hydroxylamines were converted to unsaturated and saturated secondary amines. The thermal decomposition of a mixture of he cis and trans isomers of N-methyl-alpha-pipecoline oxide formed the expected N-methyl-N-5-hexenylhydroxylamine as well as a saturated bicyclic product, formulated as cis-N-methyl-3-oxa-2-azabicyclo [3.3.01 octane. A possible mechanism for the formation of this product is presented. The cis and trans isomers of N-methyl-a-pipecoline oxide have been separated and characterized. Each Of the isomers has been pyrolyzed separately and only trans-N-methyl-a-pipecoline oxide formed the expected unsaturated hydroxylamine.