2-Ethylcyclopentanone oxime | 98435-37-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Ethylcyclopentanone oxime
• 英文别名: 2-ethyl-cyclopentanone oxime；2-Aethyl-cyclopentanon-oxim；(NE)-N-(2-ethylcyclopentylidene)hydroxylamine
• CAS: 98435-37-1
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: CNPFATBNRILXCU-BQYQJAHWSA-N

物化性质

• 沸点：
  215.7±9.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Ethylcyclopentanone oxime 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 Petroleum ether 为溶剂， 反应 4.0h， 生成 trans-N-(Diphenylphosphinyl)-2-ethylcyclopentylamine
  参考文献：
  名称：

  Stereoselective Hydride Reductions of Cyclic N-Diphenylphosphinyl Imines. Highly Diastereoselective Syntheses of Protected Primary Amines

  摘要：

  Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.

  DOI：

  10.1021/jo00128a009
• 作为产物：
  描述：

  2-乙基环戊酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 以80%的产率得到2-Ethylcyclopentanone oxime
  参考文献：
  名称：

  Stereoselective Hydride Reductions of Cyclic N-Diphenylphosphinyl Imines. Highly Diastereoselective Syntheses of Protected Primary Amines

  摘要：

  Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.

  DOI：

  10.1021/jo00128a009

文献信息

• The Beckmann Rearrangement of Certain 2-Alkyl Cyclopentanone and Cyclohexanone Oximes^1,2
  作者：John G. Hildebrand、Marston Taylor Bogert

  DOI：10.1021/ja01295a036

  日期：1936.4
• Hueckel; Gelmroth, Justus Liebigs Annalen der Chemie, 1934, vol. 514, p. 233,245
  作者：Hueckel、Gelmroth

  DOI：——

  日期：——
• BRENNAN, THOMAS M.;HENDRICK, MICHAEL E.
  作者：BRENNAN, THOMAS M.、HENDRICK, MICHAEL E.

  DOI：——

  日期：——
• US5171872A
  申请人：——

  公开号：US5171872A

  公开（公告）日：1992-12-15
• Stereoselective Hydride Reductions of Cyclic N-Diphenylphosphinyl Imines. Highly Diastereoselective Syntheses of Protected Primary Amines
  作者：Robert O. Hutchins、Jeffrey Adams、Melvin C. Rutledge

  DOI：10.1021/jo00128a009

  日期：1995.11

  Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.