4(S)-chloro-5-formyloxypent-2-enonitrile | 222837-47-0

• 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: 4(S)-chloro-5-formyloxypent-2-enonitrile
• 英文别名: [(Z,2S)-2-chloro-4-cyanobut-3-enyl] formate
• CAS: 222837-47-0
• 化学式: C₆H₆ClNO₂
• 分子量: 159.572
• InChiKey: BJELJRXCHPDUFN-UDIFJAKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4(S)-chloro-5-formyloxypent-2-enonitrile 在 吡啶 作用下， 反应 24.0h， 以86%的产率得到(Z)-3-chloro-1-cyanobuta-1,3-diene
  参考文献：
  名称：

  Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone

  摘要：

  Regiospecific C-5-halogenation with retention of configuration occurred upon Beckman fragmentation of levoglucosenone oxime using SOCl2 or PBr3. On the other hand, the oxime of its dihydro derivative gave under these conditions the C-6- substitution product. A stereoselective synthetic scheme for (+)-gamma-pelargonolactone, an attractant for the rice and corn weevils Sitophiltus zeamais, was developed from the fragmentation product of levoglucosenone oxime.

  DOI：

  10.1023/b:conc.0000018110.36123.f2
• 作为产物：
  描述：

  1,6-anhydro-3,4-dideoxy-β-D-glycerohex-3-enopyranos-2-ulose oxime 在 氯化亚砜 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以65%的产率得到4(S)-chloro-5-formyloxypent-2-enonitrile
  参考文献：
  名称：

  Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone

  摘要：

  Regiospecific C-5-halogenation with retention of configuration occurred upon Beckman fragmentation of levoglucosenone oxime using SOCl2 or PBr3. On the other hand, the oxime of its dihydro derivative gave under these conditions the C-6- substitution product. A stereoselective synthetic scheme for (+)-gamma-pelargonolactone, an attractant for the rice and corn weevils Sitophiltus zeamais, was developed from the fragmentation product of levoglucosenone oxime.

  DOI：

  10.1023/b:conc.0000018110.36123.f2

文献信息

• Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone
  作者：F. A. Valeev、E. V. Gorobets、I. P. Tsypysheva、G. Sh. Singizova、L. Kh. Kalimullina、M. G. Safarov、O. V. Shitikova、M. S. Miftakhov

  DOI：10.1023/b:conc.0000018110.36123.f2

  日期：2003.11

  Regiospecific C-5-halogenation with retention of configuration occurred upon Beckman fragmentation of levoglucosenone oxime using SOCl2 or PBr3. On the other hand, the oxime of its dihydro derivative gave under these conditions the C-6- substitution product. A stereoselective synthetic scheme for (+)-gamma-pelargonolactone, an attractant for the rice and corn weevils Sitophiltus zeamais, was developed from the fragmentation product of levoglucosenone oxime.