ethyl 2-ethyl-1-cyclopentenecarboxylate | 138542-04-8

• 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: ethyl 2-ethyl-1-cyclopentenecarboxylate
• 英文别名: Ethyl 2-ethylcyclopentene-1-carboxylate
• CAS: 138542-04-8
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: OEQLJAAWFCKVQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-ethyl-1-cyclopentenecarboxylate 在 Rh on carbon lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 100.0 ℃ 、586.06 kPa 条件下， 反应 0.5h， 生成 cis-(2-ethylcyclopent-1-yl)methanol
  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：

  1,2-二溴环戊烯 在 叔丁基锂 作用下， 反应 1.08h， 生成 ethyl 2-ethyl-1-cyclopentenecarboxylate
  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

• [DE] SUBSTITUIERTE VINYL- UND ALKINYL-CYCLOHEXENOLE ALS WIRKSTOFFE GEGEN ABIOTISCHEN PFLANZENSTRESS<br/>[EN] SUBSTITUTED VINYL AND ALKINYL CYCLOHEXENOLS AS ACTIVE AGENTS AGAINST ABIOTIC STRESS IN PLANTS<br/>[FR] VINYL- ET ALCINYL-CYCLOHEXÉNOLS SUBSTITUÉS EN TANT QUE PRINCIPES ACTIFS CONTRE LE STRESS ABIOTIQUE DES VÉGÉTAUX
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2012139891A1

  公开（公告）日：2012-10-18

  Die Erfindung betrifft substituierte Vinyl- und Alkinyl-cyclohexenole der allgemeinen Formel (I) und deren Salze, wobei die Reste R1, R2, R3, R4, R5, [X-Y] und Q die in der Beschreibung angegebenen Definitionen besitzen, Verfahren zu deren Herstellung und ihre Verwendung zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, und/oder zur Erhöhung des Pflanzenertrags.
• Stereochemistry of metal-halogen exchange-initiated intramolecular conjugate addition reactions in the construction of 5-membered carbocycles
  作者：Manning P. Cooke

  DOI：10.1021/jo00031a031

  日期：1992.2

  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.