1-(3,4-亚甲基二氧苯基)-1-丁烯 | 16929-04-7

• 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
• 中文名称: 1-(3,4-亚甲基二氧苯基)-1-丁烯
• 英文名称: 1-(3,4-Methylenedioxyphenyl)-1-butene
• 英文别名: (E)-5-(but-1-en-1-yl)benzo[d][1,3]dioxole；5-[(E)-but-1-enyl]-1,3-benzodioxole
• CAS: 16929-04-7
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: ZLMZMSBNIVMXHF-ONEGZZNKSA-N

物化性质

• 沸点：
  266.7±25.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 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：

  1-(3,4-亚甲基二氧苯基)-1-丁烯 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 10.5h， 生成 外消旋MBDB盐酸（外消旋N-甲基-1-（3,4-亚甲二氧苯基）-2-丁胺盐酸盐）标准品
  参考文献：
  名称：

  Henry condensation at high pressures

  摘要：

  DOI：

  10.1007/bf00960337
• 作为产物：
  描述：

  1-(1,3-benzodioxol-5-yl)butan-1-ol 在 potassium hydrogensulfate 作用下， 以91%的产率得到1-(3,4-亚甲基二氧苯基)-1-丁烯
  参考文献：
  名称：

  Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class

  摘要：

  The alpha-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related alpha-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate. Stimulus generalization occurred with the racemate and the R-(-) enantiomer of the alpha-methyl homologue and the S-(+) enantiomer of the alpha-ethyl primary amine. No generalization occurred with the other enantiomers or with the N-methyl derivatives of either series. Human psychopharmacology studies revealed that the N-methyl derivative of the title compound was nonhallucinogenic and that it had a new, novel psychoactive effect. It is suggested that this compound is the prototype of a new pharmacologic class that may have value in facilitating psychotherapy and that this class be designated as entactogens.

  DOI：

  10.1021/jm00160a035

文献信息

• Molybdenum hexacarbonyl as a thiophilic metal raagent: desulfenylative allylation using allylic sulfides
  作者：Yoshiro Masuyama、Kohji Yamada、Yasuhiko Kurusu

  DOI：10.1016/s0040-4039(00)95751-4

  日期：1987.1

  Molybdenum hexacarbonyl is a useful reagent for desulfenylative allylation of carbon nucleophiles with allylic sulfides.

  六羰基钼是用于将碳亲核试剂与烯丙基硫化物进行脱硫烯基化烯丙基化的有用试剂。
• Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequent <i>in situ</i> functionalization
  作者：Guo-Ming Ho、Lucas Segura、Ilan Marek

  DOI：10.1039/d0sc02542a

  日期：——

  The stereoselective preparation of synthetically versatile vinylboronates from ω-alkenylboronates is achieved through a ruthenium-catalyzed isomerization reaction. A variety of di- and trisubstituted vinylboronates were conveniently produced and could be used as a new starting point for subsequent in situ remote functionalization through either a sequential Ru/Pd or Ru/Cu double catalytic system.

  通过钌催化的异构化反应，可以从ω-烯基硼酸酯中立体选择性地制备合成用途的乙烯基硼酸酯。可以方便地生产各种二取代和三取代的乙烯基硼酸酯，它们可以用作随后通过连续Ru / Pd或Ru / Cu双催化系统进行原位远程官能化的新起点。
• Hexacarbonylmolybdenum(0)-Induced Dechalcogenization of Allylic Sulfides, Sulfones, and Selenides: Nucleophilic Substitution and Reductive Dechalcogenization
  作者：Yoshiro Masuyama、Kohji Yamada、Soh-hei Shimizu、Yasuhiko Kurusu

  DOI：10.1246/bcsj.62.2913

  日期：1989.9

  Hexacarbonylmolybdenum(0)-induced dechalcogenization of allylic sulfides I, sulfones II, and selenides III in refluxing dioxane, which led to nucleophilic substitutions with carbon nucleophiles. Attack of the relatively bulky nucleophile, 2-ethoxycarbonyl-2-sodiocyclopentanone occurred regioselectively at the less substituted end of the allyl unit after the dechalcogenization to give only one isomer

  六羰基钼 (0) 诱导的烯丙基硫化物 I、砜 II 和硒化物 III 在回流的二恶烷中脱硫，导致碳亲核试剂发生亲核取代。相对庞大的亲核试剂 2-乙氧羰基-2-钠基环戊酮的攻击在脱硫后烯丙基单元的较少取代末端发生区域选择性，仅产生一种异构体。钠丙二酸二乙酯对 I 和 III 的攻击优先发生在 γ 位，而对 II 的攻击优先发生在脱磺酰化后烯丙基单元的更多取代端。在没有碳亲核试剂的情况下，在回流的二恶烷中用 Mo(CO)6 处理​​ I、II 和 III 导致还原性脱硫。H2O 的加入加速了还原脱硫。
• Benzodioxale derivatives
  申请人：Eisai Co., Ltd.

  公开号：US05110956A1

  公开（公告）日：1992-05-05

  A new benzodioxole derivative has a substituent in the phenyl ring which is a carboxyalkylthioalkyl or the like and is effective to treat a liver disease.

  一种新的苯二氧杂环己烷衍生物在苯环中具有一个羧基烷硫烷基或类似物的取代基，可有效治疗肝病。
• Iron-Catalyzed Tunable and Site-Selective Olefin Transposition
  作者：Xiaolong Yu、Haonan Zhao、Ping Li、Ming Joo Koh

  DOI：10.1021/jacs.0c08631

  日期：2020.10.21

  earth-abundant iron-based complex, a base and a boryl compound promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from

  CC 双键的催化异构化是必不可少的化学转化，用于提供更高价值的类似物，在化学工业中具有重要用途。尽管在该领域取得了进展，但仍然迫切需要一种通用催化解决方案，能够精确控制环状和非环状体系中的 C=C 键迁移位置，以提供二取代和三取代烯烃。在这里，我们展示了催化量的合适的地球丰富的铁基络合物、碱和硼基化合物促进有效和可控的烯烃转位。机理研究表明，这些过程可能涉及原位形成铁氢化物物种，该物种通过顺序烯烃插入/β-氢化物消除促进烯烃异构化。通过这个策略，