2-烯丙基戊酸甲酯 | 210690-89-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-烯丙基戊酸甲酯
• 英文名称: methyl 2-allylpentanoate
• 英文别名: 2-Propyl-4-pentenoic Acid Methyl Ester；methyl 2-propylpent-4-enoate
• CAS: 210690-89-4
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: FDPCGENVCAREOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2-烯丙基戊酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.5h， 生成 Trimethyl-((Z)-2-propyl-penta-2,4-dienyl)-silane
  参考文献：
  名称：

  Highly selective trapping of unsymmetrical pentadienyl anions by silicon and tin electrophiles. Marked contrast between kinetic and thermodynamic control of product composition

  摘要：

  The nucleophilic reaction of lithium and potassium salts of five pentadienyl anions bearing sterically and/or coordinatively different groups at their unsymmetrical 2-position toward Me3SiCl and Me3SnBr is described. When the anion of the potassium salt was trapped by Me3SiCl, (Z)-4-substituted-pentadienylsilanes were obtained with high selectivity (87-100%). The lithium salt, however, gave a mixture of (E)- and (Z)-4-substituted-pentadienylsilanes. The coupling reaction proceeds under kinetic control, because the product composition from Si trapping reflected the structure of the parent dienyl anion and the steric interaction between the incoming Me3Si group and the substituent on the anion. In contrast, when the anion was trapped by Me3SnBr under the identical conditions, (Z)-2-substituted-pentadienyltins were formed with 60-96% selectivity. Only relatively small changes in product composition, as a function of the cation or the substituent on the anion, were observed. These results could be explained by thermodynamic controlling factors, including a 1,5-Me3Sn shift, and a redistribution of pentadienyl groups under basic conditions.

  DOI：

  10.1021/jo00006a011
• 作为产物：
  描述：

  戊酸甲酯 、 3-溴丙烯 在 lithium diisopropyl amide 、 N,N-二甲基丙烯基脲 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以80%的产率得到2-烯丙基戊酸甲酯
  参考文献：
  名称：

  16-氯-1-脱氢长春花青碱与醇钠反应的稳定两性离子衍生物

  摘要：

  用甲醇钠处理16-氯-1-脱氢长春花碱2a和16-氯-1-脱氢烟碱二十二碳酸钠2b分别产生16-甲氧基吲哚肾上腺素11a对11b，以及两个甜菜碱12a对12b和14a对14b。除不存在16-乙氧基吲哚胺外，乙醇钠的结果相似。通过其光谱数据，化学相关性以及转化为化合物26来确定所有衍生物的结构，化合物26的外消旋物是通过全合成制备的。与前面描述的2a，b反应相反在醇中，在醇盐的影响下，内部螺栓连接的两性离子衍生物12-15的形成似乎决定了反应路径。

  DOI：

  10.1016/s0040-4020(98)00293-2

文献信息

• Stabilized zwitterionic derivatives from the reaction of 16-chloro-1-dehydrovincadifformine with sodium alkoxides
  作者：Daniel Royer、Yang Liu Yu、Georgette Hugel、Jean Lévy

  DOI：10.1016/s0040-4020(98)00293-2

  日期：1998.6

  Treatment of 16-chloro-1-dehydrovincadifformine 2a and 16-chloro-1-dehydrotabersonine 2b with sodium methoxide respectively yielded the 16-methoxyindolenines 11avs11b, and the two betaines 12avs12b and 14avs14b. Sodium ethoxide gave similar results, except for the absence of the 16-ethoxyindolenines. The structures of all derivatives were ascertained by their spectroscopic data, by chemical correlations

  用甲醇钠处理16-氯-1-脱氢长春花碱2a和16-氯-1-脱氢烟碱二十二碳酸钠2b分别产生16-甲氧基吲哚肾上腺素11a对11b，以及两个甜菜碱12a对12b和14a对14b。除不存在16-乙氧基吲哚胺外，乙醇钠的结果相似。通过其光谱数据，化学相关性以及转化为化合物26来确定所有衍生物的结构，化合物26的外消旋物是通过全合成制备的。与前面描述的2a，b反应相反在醇中，在醇盐的影响下，内部螺栓连接的两性离子衍生物12-15的形成似乎决定了反应路径。
• US4260552A
  申请人：——

  公开号：US4260552A

  公开（公告）日：1981-04-07
• Examining the correlations between GSK-3 inhibitory properties and anti-convulsant efficacy of valproate and valproate-related compounds
  作者：Geoff H. Werstuck、Anna J. Kim、Timothy Brenstrum、Stephan A. Ohnmacht、Ella Panna、Alfredo Capretta

  DOI：10.1016/j.bmcl.2004.09.013

  日期：2004.11

  A family of compounds based upon the chemical structure of valproate were synthesized and assayed for their ability to inhibit glycogen synthase kinase (GSK)-3 alpha and beta activity in vitro. This data is correlated to the known anti-convulsant properties of these compounds in order to determine the potential role of GSK-3 inhibition in the therapeutic efficacy of these drugs. (C) 2004 Elsevier Ltd. All rights reserved.
• Highly selective trapping of unsymmetrical pentadienyl anions by silicon and tin electrophiles. Marked contrast between kinetic and thermodynamic control of product composition
  作者：Yoshinori Naruta、Yutaka Nishigaichi、Kazuhiro Maruyama

  DOI：10.1021/jo00006a011

  日期：1991.3

  The nucleophilic reaction of lithium and potassium salts of five pentadienyl anions bearing sterically and/or coordinatively different groups at their unsymmetrical 2-position toward Me3SiCl and Me3SnBr is described. When the anion of the potassium salt was trapped by Me3SiCl, (Z)-4-substituted-pentadienylsilanes were obtained with high selectivity (87-100%). The lithium salt, however, gave a mixture of (E)- and (Z)-4-substituted-pentadienylsilanes. The coupling reaction proceeds under kinetic control, because the product composition from Si trapping reflected the structure of the parent dienyl anion and the steric interaction between the incoming Me3Si group and the substituent on the anion. In contrast, when the anion was trapped by Me3SnBr under the identical conditions, (Z)-2-substituted-pentadienyltins were formed with 60-96% selectivity. Only relatively small changes in product composition, as a function of the cation or the substituent on the anion, were observed. These results could be explained by thermodynamic controlling factors, including a 1,5-Me3Sn shift, and a redistribution of pentadienyl groups under basic conditions.