3-Benzo[1,3]dioxol-4-yl-propionyl chloride | 124400-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-Benzo[1,3]dioxol-4-yl-propionyl chloride
• 英文别名: 3-(1,3-Benzodioxol-4-yl)propanoyl chloride
• CAS: 124400-01-7
• 化学式: C₁₀H₉ClO₃
• 分子量: 212.633
• InChiKey: FRSKKXLTNOUQGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Benzo[1,3]dioxol-4-yl-propionyl chloride 在 四氯化钛 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以3.6 g的产率得到4,5-(methylenedioxy)-1-indanone
  参考文献：
  名称：

  通过 Aza-Heck 环化全合成 (±)-Impatien A

  摘要：

  描述了天然产物凤仙花 A 的首次全合成。这种简洁的合成以 aza-Heck 环化为特征，以构建复杂的螺环系统，并为在复杂分子合成中使用 aza-Heck 环化提供了一个罕见的例子。为了实现亲电子氮原子与四取代烯烃的关键环化，我们利用高通量实验来鉴定新的配体，并最终通过已知化合物的七个步骤提供凤仙花 A。

  DOI：

  10.1021/acs.orglett.1c02767
• 作为产物：
  描述：

  2,3-(methylenedioxy)cinnamic acid 在 palladium on activated charcoal 氯化亚砜 、 氢气 作用下， 以 乙醇 、 苯 为溶剂， 反应 8.0h， 生成 3-Benzo[1,3]dioxol-4-yl-propionyl chloride
  参考文献：
  名称：

  Nonneurotoxic tetralin and indan analogs of 3,4-(methylenedioxy)amphetamine (MDA)

  摘要：

  Four cyclic analogues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied. These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Two groups of rats were trained to discriminate either LSD tartrate (0.08 mg/kg) from saline, or (+/-)-MDMA.HCl (1.75 mg/kg) from saline. In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine 1-(2,5-dimethoxy-4- methylphenyl)-2-aminopropane (DOM) were also evaluated. None of the methylenedioxy compounds substituted in LSD-trained rats, while both 3a and 3b fully substituted in MDMA-trained rats. Compounds 4a and 4b did not substitute in MDMA-trained rats. Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart. In view of the now well-established serotonin neurotoxicity of 3,4-(methylenedioxy)amphetamine and its N-methyl homologue 1, 3a and 3b were evaluated and compared to 1 for similar toxic effects following a single acute dose of 40 mg/kg sc. Sacrifice at 1 week showed that neither 3a nor 3b depressed rat cortical or hippocampal 5-HT or 5-HIAA levels nor were the number of binding sites (Bmax) depressed for [3H]paroxetine. By contrast, and in agreement with other reports, 1 significantly depressed all three indices of neurotoxicity. These results indicate that 3a and 3b have acute behavioral pharmacology similar to 1 but that they lack similar serotonin neurotoxicity.

  DOI：

  10.1021/jm00164a037