(E)-2-[2-(2-bromophenyl)vinyl]-1,3-dioxolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-[2-(2-bromophenyl)vinyl]-1,3-dioxolane
• 英文别名: 2-[(E)-2-(2-bromophenyl)ethenyl]-1,3-dioxolane
• 化学式: C₁₁H₁₁BrO₂
• 分子量: 255.111
• InChiKey: IMWXTUDOTOUOMF-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-苄基哌啶酮 、 (E)-2-[2-(2-bromophenyl)vinyl]-1,3-dioxolane 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.58h， 以31%的产率得到(E)-1-benzyl-4-{2-[2-(1,3-dioxolan-2yl)vinyl]phenyl}piperidin-4-ol
  参考文献：
  名称：

  Synthesis, pharmacological activity and structure affinity relationships of spirocyclic σ1 receptor ligands with a (2-fluoroethyl) residue in 3-position

  摘要：

  In order to develop a fluorinated radiotracer for imaging of sigma(1) receptors in the central nervous system a series of (2-fluoroethyl) substituted spirocyclic piperidines 3 has been prepared. In the key step of the synthesis 2-bromocinnamaldehyde acetal 5 was added to piperidones 6 with various substituents at the N-atom. Unexpectedly, this reaction led to 2-benzoxepines 8, which were contracted with acid to afford the spirocyclic 2-benzofuranacetaldehydes 9. The best yields were obtained, when the transformations up to the alcohols 10 were performed without isolation of intermediates. Generally the (2-fluoroethyl) derivatives 3 have higher sigma(1) affinity and sigma(1)/sigma(2) selectivity than the corresponding (3-fluoropropyl) derivatives 2. The most promising candidate for the development as radiotracer is the (2-fluoroethyl) derivative 3a (WMS-1828, fluspidine, 1'-benzyl-3-(2-fluoroethyl)-3H-spiro[[2]benzofuran-1,4'-piperidine]), which shows subnanomolar sigma(1) affinity (K-i = 0.59 nM) and excellent selectivity over the sigma(2) subtype (1331-fold) as well as some other receptor systems. The novel synthetic strategy also allows the systematic pharmacological evaluation of intermediate alcohols 10. Despite their high sigma(1) affinity (K-i = 6-32 nM) and selectivity the alcohols 10 are 10-30-fold less potent than the bioisosteric fluoro derivatives 3. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.013
• 作为产物：
  描述：

  (1,3-二氧戊环-2-基)甲基三苯基溴化瞵 、 邻溴苯甲醛 在 三(3,6-二氧杂庚基)胺 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成 (Z)-2-[2-(2-bromophenyl)vinyl]-1,3-dioxolane 、 (E)-2-[2-(2-bromophenyl)vinyl]-1,3-dioxolane
  参考文献：
  名称：

  3-取代的 1'-苄基螺[[2]苯并氧杂1,4'-哌啶]的合成和合成孔径雷达研究

  摘要：

  描述了迄今为止未知的螺 [[2] 苯并氧杂环庚烷-1,4'-哌啶] 环系统的制备。该合成由 2-溴苯甲醛 (4) 和 (1,3-二氧戊环-2-基甲基) 三苯基溴化鏻 (5) 的 Wittig 反应组成，生成 α,β-不饱和缩醛。6的双键随后被氢化。所得溴化缩醛 7 用正丁基锂处理，然后用 1-苄基哌啶-4-酮 (9) 处理，得到羟基缩醛 10。 10 与对甲苯磺酸或 HCl 水溶液的酸催化环化导致形成1'-benzylspiro[[2]benzoxepine-1,4'-piperidines] 分别为 11 和 12。螺环化合物11和12的3-位取代基通过与氰化三甲基甲硅烷或(氰基亚甲基)三苯基正膦反应进一步修饰，以分别引入具有一个或两个碳原子的残基。在体外评估了合成的化合物的σ1-和σ2-受体亲和力。最有效的 σ1 配体是甲氧基衍生物 11（Ki = 2.56 nM），而氰甲基衍生物 20

  DOI：

  10.1002/ejoc.200390111

文献信息

• Phase transfer Wittig reaction with 1,3-dioxolan-2-yl-methyltriphenyl phosphonium salts: An efficient method for vinylogation of aromatic aldehydes
  作者：Nicolas Daubresse、Charlette Francesch、Christian Rolando

  DOI：10.1016/s0040-4020(98)00631-0

  日期：1998.9

  Aldehydes were efficiently transformed into allylic dioxolanes by a Wittig-type reaction, using 1,3-dioxolan-2-yl-methyltriphenylphosphonium bromide under phase transfer conditions. The substituent kinetic effects were studied, and related to Hammett values and electrochemical potentials. (C) 1998 Elsevier Science Ltd. All rights reserved.