3-(3,4-methylenedioxyphenoxy)propyl bromide | 56219-51-3

• 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-(3,4-methylenedioxyphenoxy)propyl bromide
• 英文别名: 5-(3-bromopropoxy)benzo[d][1,3]dioxole；5-(3-bromopropoxy)-1,3-benzodioxole；5-(3-bromo-propoxy)-benzo[1,3]dioxole；5-(3-bromopropoxy)-2H-1,3-benzodioxole
• CAS: 56219-51-3
• 化学式: C₁₀H₁₁BrO₃
• mdl: MFCD11164581
• 分子量: 259.1
• InChiKey: LZVZRLKAMWQNLU-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 1 Torr)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-methylenedioxyphenoxy)propyl bromide 在 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 1-[3-(3,4-methylenedioxyphenoxy)propyl]-3-piperidone
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of 1-Oxo-2-(3-piperidyl)-1,2,3,4- tetrahydroisoquinolines and Related Analogues as a New Class of Specific Bradycardic Agents Possessing I_f Channel Inhibitory Activity

  摘要：

  A series of 1-oxo-2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinolines and related analogues were prepared and evaluated for their bradycardic activities in isolated right atrium and in anesthetized rats. (+/-)-6,7-Dimethoxy-2-{1-[3-(3,4-methylenedioxyphenoxy)propyl]-3-piperidyl}-1,2,3,4-tetrahydroisoquinoline (4) was chosen as a lead, and structural modifications were performed on the tetrahydroisoquinoline ring and the terminal aromatic ring. The modifications on the tetrahydroisoquinoline ring revealed that the 1-oxo-1,2,3,4-tetrahydroisoquinoline ring system was optimum structure for both in vitro potency and in vivo efficacy. Furthermore, methoxy, ethoxy, and methoxycarbonyl groups were identified as preferable substituents on the terminal aromatic ring. One of the 1-oxo-1,2,3,4-tetrahydroisoquinoline derivatives, (R)-10a, was further evaluated for its bradycardic activity and inhibitory activity against I-f currents. Compound (R)-10a demonstrated potent bradycardic activity in rats with minimal influence on blood pressure after oral administration. The compound also showed inhibition of I-f currents (IC50 = 0.32 muM) in guinea pig pacemaker cells.

  DOI：

  10.1021/jm0301742
• 作为产物：
  描述：

  芝麻酚 在 硫酸 、 potassium carbonate 、 sodium bromide 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 3-(3,4-methylenedioxyphenoxy)propyl bromide
  参考文献：
  名称：

  一种3-苯氧基溴丙烷或其类似物的制备方法

  摘要：

  本发明公开了一种3‑苯氧基溴丙烷或其类似物的制备方法，以廉价且易得的苯酚或其芳香酚和烯丙基化合物，经过取代反应和加成反应得到3‑苯氧基溴丙烷及其类似物产品，为避免使用气态溴化氢的不便，本发明采用溴化盐和酸原位生成高浓度氢溴酸以实现第二步加成反应，工艺操作简单、条件易控制、原子经济性好，从环境影响方面是低污染、零排放的符合当前绿色化学合成方向，从成本经济方面是由于烯烃的直接利用在很大程度上降低了成本。

  公开号：

  CN113683492A

文献信息

• N-Heterocyclic carbene–chromium-catalyzed alkylative cross-coupling of benzamide derivatives with aliphatic bromides
  作者：Jinghua Tang、Pei Liu、Xiaoming Zeng

  DOI：10.1039/c8cc05026k

  日期：——

  Described here is a chromium-catalyzed alkylative cross-coupling of benzamide derivatives with aliphatic electrophiles under mild conditions. This reaction was promoted by a low-cost and air-stable chromium(III) chloride salt combined with an N-heterocyclic carbene ligand and phenylmagnesium bromide as a reductant, and probably occurred with low-valent chromium involved in the catalytic cleavage of

  这里描述的是在温和条件下苯甲酰胺衍生物与脂肪族亲电子试剂的铬催化烷基化交叉偶联。低成本，空气稳定的氯化铬（III）盐与N-杂环卡宾配体和苯基溴化镁作为还原剂的结合促进了该反应，并且可能发生在低价铬参与邻位催化裂解的过程中苯甲酰胺的-C–H键，然后通过涉及自由基的机理与烷基溴偶联。
• (±)-2-(3-Piperidyl)-1,2,3,4-tetrahydroisoquinolines as a new class of specific bradycardic agents
  作者：Hideki Kubota、Akio Kakefuda、Toshihiro Watanabe、Yasuko Taguchi、Noe Ishii、Noriyuki Masuda、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1016/s0960-894x(03)00349-4

  日期：2003.7

  A series of (+/-)-2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinolines were prepared and their bradycardic activities were examined in isolated guinea-pigs' right atria and in anesthetized rats. Modifications on the benzyl moiety of the parent compound, 1, led to the identification of compound 11e as a potent and specific bradycardic agent.

  制备了一系列（+/-）-2-（3-哌啶基）-1，2，3，4-四氢异喹啉，并在分离的豚鼠右心房和麻醉大鼠中检查了它们的心动过缓。对母体化合物1的苄基部分进行的修饰导致将化合物11e鉴定为有效的特定缓激药。
• Indolylpiperidine derivatives as antihistaminic aand antiallergic agents
  申请人：——

  公开号：US20040116471A1

  公开（公告）日：2004-06-17

  The invention relates to indolyl piperidinyl derivatives of formula (I) wherein: A 1 represents an alkylene, alkyleneoxy, alkylenethio, alkanoylene or hydroxyalkylene group; A 2 represents an alkylene, alkyleneoxy, alkylenethio, alkanoylene or an alkyleneoxyalkylene group; W 1 represents a phenylene, furanylene or pyridinylene group which is unsubstituted or substituted by one or more halogen atoms, alkoxy groups and/or alkyl groups; W 2 represents a 3-10 membered monocyclic or bicyclic group containing from 1 to 3 heteroatoms said group being unsubstituted or substituted by one or more halogen atoms, alkyl groups, alkoxy groups and/or oxo groups; R 1 represents a hydrogen or halogen atom or an alkyl, alkoxy or methylamino group; and R 2 represents a carboxyl group; and pharmaceutically acceptable salts thereof; to processes for their preparation; to pharmaceutical compositions containing them; and to their medical use as antihistaminic and antiallergic agents.

  该发明涉及式(I)的吲哚基哌啶衍生物，其中：A1代表烷基、烷氧基、硫代烷基、烷酰基或羟基烷基基团；A2代表烷基、烷氧基、硫代烷基、烷酰基或烷氧基烷基基团；W1代表苯基、呋喃基或吡啶基，该基团未取代或被一个或多个卤素原子、烷氧基和/或烷基取代；W2代表含有1至3个杂原子的3-10元成员的单环或双环基团，该基团未取代或被一个或多个卤素原子、烷基、烷氧基和/或氧代基取代；R1代表氢原子或卤素原子或烷基、烷氧基或甲氧基氨基基团；R2代表羧基；及其药学上可接受的盐；其制备方法；含有它们的药物组合物；以及它们作为抗组胺和抗过敏药物的医药用途。
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSES ORGANIQUES
  申请人：SPEEDEL EXPERIMENTA AG

  公开号：WO2005061457A1

  公开（公告）日：2005-07-07

  Novel substituted piperidines of the general formulae (I) and (II) with the substituent definitions as explained in detail in the description are described. The compounds are suitable in particular as renin inhibitors and are highly potent.

  描述了一种具有一般式(I)和(II)的新型替代哌啶化合物，其中详细说明了取代基定义。这些化合物特别适用作为肾素抑制剂，并且具有很高的效力。
• Alkylenedioxybenzene derivatives and acid addition salts thereof
  申请人：Mitsubishi Chemical Industries Limited

  公开号：US04684739A1

  公开（公告）日：1987-08-04

  Alkylenedioxybenzene derivatives are prepared and found to be useful as pharmaceutical agents, particularly as hypotensives.

  烷二氧基苯衍生物被制备出来，并发现它们作为药物代理特别是降压药物非常有用。