5-氯-2-乙基戊醛 | 62498-23-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 中文名称: 5-氯-2-乙基戊醛
• 英文名称: 5-chloro-2-ethylpentanal
• 英文别名: 2-ethyl-5-chloropentanal
• CAS: 62498-23-1
• 化学式: C₇H₁₃ClO
• mdl: MFCD19232376
• 分子量: 148.633
• InChiKey: NGQQRRPIPBXQQI-UHFFFAOYSA-N

物化性质

• 沸点：
  196.8±23.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-氯-2-乙基戊醛 在 正丁基锂 、 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 0.43h， 生成 tert-butyl (cis-2-ethylcyclopent-1-yl)acetate
  参考文献：
  名称：

  Stereochemistry of metal-halogen exchange-initiated intramolecular conjugate addition reactions in the construction of 5-membered carbocycles

  摘要：

  The stereochemistry of some lithium-iodine exchange-initiated cyclization reactions of model omega-iodo, gamma-substituted activated olefins has been studied. The stereoselectivities of these anionic cyclization reactions have been found to be a function of the olefin activator employed, reaction conditions, Michael acceptor olefin geometry, the nature of the gamma-substituent, and, in some cases, the presence of additives. Cyclization reactions of iodides possessing E olefin geometry give a moderate preference for trans cyclopentane formation while Z olefin geometry leads to extremely high (> 300:1) trans product selectivity. Cyclization reactions of E olefins under radical conditions were found to be slightly more trans-selective than those observed under anionic conditions although Z olefin geometry again promotes very high trans product selectivity. The presence of the allylic methoxyl group in (E)-7d leads to cis selectivity under both anionic and radical conditions. Intramolecular complexation involving the reactive carbon center and the methoxyl group is suggested in both modes as a possible explanation for this cis product selectivity.

  DOI：

  10.1021/jo00031a031
• 作为产物：
  描述：

  5-氯戊酸乙酯 在 正丁基锂 、 二异丁基氢化铝 、 二异丙胺 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 14.91h， 生成 5-氯-2-乙基戊醛
  参考文献：
  名称：

  Stereochemistry of metal-halogen exchange-initiated intramolecular conjugate addition reactions in the construction of 5-membered carbocycles

  摘要：

  The stereochemistry of some lithium-iodine exchange-initiated cyclization reactions of model omega-iodo, gamma-substituted activated olefins has been studied. The stereoselectivities of these anionic cyclization reactions have been found to be a function of the olefin activator employed, reaction conditions, Michael acceptor olefin geometry, the nature of the gamma-substituent, and, in some cases, the presence of additives. Cyclization reactions of iodides possessing E olefin geometry give a moderate preference for trans cyclopentane formation while Z olefin geometry leads to extremely high (> 300:1) trans product selectivity. Cyclization reactions of E olefins under radical conditions were found to be slightly more trans-selective than those observed under anionic conditions although Z olefin geometry again promotes very high trans product selectivity. The presence of the allylic methoxyl group in (E)-7d leads to cis selectivity under both anionic and radical conditions. Intramolecular complexation involving the reactive carbon center and the methoxyl group is suggested in both modes as a possible explanation for this cis product selectivity.

  DOI：

  10.1021/jo00031a031

文献信息

• Synthesis of the Aspidosperma Alkaloid Na-Formyl-16-α-Hydroxyaspidospermidine
  作者：Fatiha Belferdi、Abdelhamid Belattar

  DOI：10.3390/61000803

  日期：——

  The first total synthesis of Na-formyl-16α-hydroxyaspidospermidine and its isomer via (°)-vincadifformine is described and their structure elucidation using different methods of analysis is reported.

  描述了 Na-formyl-16α-hydroxyaspidospermidine 及其异构体通过 (°)-vincadifformine 的首次全合成, 并报告了使用不同分析方法对其结构的解析。
• Etude des aldimines lithiees
  作者：Jean-Francois Le Borgne

  DOI：10.1016/s0022-328x(00)80603-8

  日期：1976.12

  Aldimines are conveniently metallated, at a position α to the functional group, by using very powerful bases i.e. activated lithium dialkylamides generated in situ from lithium and a secondary amine in benzene/hexamethylphosphoric triamide. The anions obtained are alkylated with various ω,ω′-dihalogenoalkanes to give, after aqueous acid hydrolysis, good yields of ω-halogenated aldehydes and dialdehydes

  通过使用非常强大的碱，即由锂和仲胺在苯/六甲基磷三酰胺中原位生成的活化的二烷基酰胺化锂，可以方便地在官能团的位置α处将金属亚胺金属化。酸水解后，所得的阴离子用各种ω，ω'-二卤代烷烃烷基化，可得到ω-卤代醛和二醛的良好收率。
• Szabo, Lajos; Nagy, Tamas; Kalaus, Gyoergy, ACH - Models in Chemistry, 1998, vol. 135, # 4, p. 641 - 652
  作者：Szabo, Lajos、Nagy, Tamas、Kalaus, Gyoergy、Szantay, Csaba

  DOI：——

  日期：——
• HAJICEK, J.;TROJANEK, J.
  作者：HAJICEK, J.、TROJANEK, J.

  DOI：——

  日期：——
• Procédé de synthèse de la vincadifformine et des dérivés apparentés à celle-ci, produits intermédiaires obtenus pendant cette synthèse et procédé pour leur préparation
  申请人：OMNICHEM Société anonyme

  公开号：EP0011057B1

  公开（公告）日：1983-02-09