2-(3-溴丙氧基)-1,3-二甲基-苯 | 3245-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(3-溴丙氧基)-1,3-二甲基-苯
• 英文名称: 2-(3-bromopropoxy)-1,3-dimethylbenzene
• CAS: 3245-54-3
• 化学式: C₁₁H₁₅BrO
• mdl: MFCD00596680
• 分子量: 243.143
• InChiKey: OILQSIAPINGGQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  140-142 °C(Press: 12 Torr)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-溴丙氧基)-1,3-二甲基-苯 在 肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-[3-(2,6-dimethylphenoxy)propylamino]guanidine
  参考文献：
  名称：

  芳氧基烷基氨基胍。它们的合成和生物学特性。

  摘要：

  DOI：

  10.1021/jm00315a024
• 作为产物：
  描述：

  3-(2,6-dimethyl-phenoxy)-propan-1-ol 在 三溴化磷 作用下， 生成 2-(3-溴丙氧基)-1,3-二甲基-苯
  参考文献：
  名称：

  The Claisen Rearrangement of Phenyl Allyl Ethers, Labeled with Carbon-14

  摘要：

  DOI：

  10.1021/ja01143a013

文献信息

• Asymmetric Synthesis of Nonracemic Primary Amines via Spiroborate-Catalyzed Reduction of Pure (<i>E</i>)- and (<i>Z</i>)-<i>O</i>-Benzyloximes: Applications toward the Synthesis of Calcimimetic Agents
  作者：Wenhua Ou、Sandraliz Espinosa、Héctor J. Meléndez、Silvia M. Farré、Jaime L. Alvarez、Valerie Torres、Ileanne Martínez、Kiara M. Santiago、Margarita Ortiz-Marciales

  DOI：10.1021/jo400371x

  日期：2013.6.7

  Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst

  使用衍生自稳定的螺硼酸酯，通过硼烷介导的单一异构体 ( E )- 和 ( Z ) -O-苄基肟醚的还原，合成了高对映体纯的 (1-芳基)-和 (1-萘基)-1-乙胺( S )-二苯基缬氨醇和乙二醇作为手性催化剂。伯 ( R )-芳基乙胺是通过使用 15% 的催化剂将纯 ( Z )-乙酮肟醚还原至 99% ee来制备的。描述了使用对映纯(1-萘-1-基)乙胺作为手性前体合成新的和已知的拟钙剂类似物的两种方便且容易的方法。
• Synthesis and Investigation of <i>S</i>-Substituted 2-Mercaptobenzoimidazoles as Inhibitors of Hedgehog Signaling
  作者：Simone Gräßle、Steven Susanto、Sonja Sievers、Emel Tavsan、Martin Nieger、Nicole Jung、Stefan Bräse

  DOI：10.1021/acsmedchemlett.7b00100

  日期：2017.9.14

  Due to the arising resistance of common drugs targeting the Hedgehog signaling pathway, the identification of new compound classes with inhibitory effect is urgently needed. We were able to identify S-alkylated 2-mercaptobenzoimidazoles as a new compound class that exhibits Hedgehog signaling activity in a low micromolar range. The scope of the 2-mercaptobenzoimidazole motif has been investigated by

  由于针对Hedgehog信号传导途径的常见药物出现耐药性，因此迫切需要鉴定具有抑制作用的新化合物。我们能够鉴定出S-烷基化的2-巯基苯并咪唑为一种新的化合物类别，该化合物在低微摩尔范围内表现出刺猬信号的活性。已经通过各种衍生物的合成研究了2-巯基苯并咪唑基序的范围，揭示了相对于化合物类别的活性，接头单元的伸长和特定取代模式的交换是可容忍的。
• Selectivity in Alkylation of Phenols with 1-Bromo-3-chloropropane Using Phase-Transfer Catalysis
  作者：E. Reinholz、A. Becker、B. Hagenbruch、S. Schäfer、A. Schmitt

  DOI：10.1055/s-1990-27096

  日期：——

  The use of various phase-transfer catalysts in the alkylation of phenol and substituted phenols with 1-bromo-3-chloropropane was investigated. When a quarternary ammonium salt of the general formula R′4N+ X-, where R′ = alkyl with a minimum chain length of 4 was used, a mixture of 1-aryloxy-3-chloropropane and 1-aryloxy-3-bromopropane resulted. The effect of counterion, added potassium bromide, and catalysts other than quarternary ammonium salts were assessed for the halopropylation of 2,5-dimethylphenol.

  研究了在1-溴-3-氯丙烷与酚及其取代酚的烷基化反应中使用各种相转移催化剂的情况。当使用一般式为R′4N+ X-的季铵盐时，其中R′为最小链长为4的烷基，结果得到1-芳氧-3-氯丙烷和1-芳氧-3-溴丙烷的混合物。评估了对2,5-二甲基酚进行卤丙基化反应时，反离子、添加的溴化钾以及其他催化剂（除了季铵盐）的影响。
• Regio- and Stereoselective Alkylboration of Endocyclic Olefins Enabled by Nickel Catalysis
  作者：Chao Ding、Yaoyu Ren、Caocao Sun、Jiao Long、Guoyin Yin

  DOI：10.1021/jacs.1c09214

  日期：2021.12.8

  construction of diversely substituted saturated heterocycles, direct and modular access is currently limited to the mono-, 2,3-, or 3,4-substitution pattern. This Communication describes the straightforward and modular construction of 2,4-substituted saturated heterocycles from readily available materials in a highly stereo- and regioselective manner, which sets the stage for numerous readily accessible

  尽管人们对快速构建不同取代的饱和杂环很感兴趣，但直接和模块化的访问目前仅限于单、2,3-或 3,4-取代模式。该通讯描述了以高度立体和区域选择性的方式从容易获得的材料中直接和模块化构建 2,4-取代饱和杂环，这为许多容易获得的药物基序奠定了基础。该策略依赖于链式行走催化。
• 2-Aryloxytetrahydrofurans. Their Reductive Cleavage by Ether Solutions of AlH₂Cl and their Cleavage and Rearrangement by Ether Solutions of AlCl₃
  作者：P. C. Loewen、R. K. Brown

  DOI：10.1139/v72-579

  日期：1972.11.15

  The hydrogenolysis of 2-aryloxytetrahydrofurans by excess AlH₂Cl gave, in excellent yield, only those products expected from exo C—O bond cleavage regardless of the nature of the substituent in the aryl ring. None of the 4-aryloxy-1-butanol, the product expected from ring cleavage, was detected. The reaction was very much faster than the corresponding AlH₂Cl hydrogenolysis of 2-alkoxytetrahydrofurans which is known to give only ring cleavage products under similar conditions.Treatment of 2-aryloxytetrahydrofurans or pyrans with AlCl₃ in ether, resulted in acid-catalyzed cleavage to the corresponding phenol and dihydrofuran or dihydropyran, the latter immediately forming polymeric products. For those 2-aryloxytetrahydrofurans or pyrans, unsubstituted, or substituted with electron donor groups in the aryl ring, another product was obtained which resulted from electrophilic attack of one protonated dihydrofuran or pyran on the ortho or para position of the phenol. These rearrangement products were also obtained in small amounts as byproducts when 2-aryloxytetrahydrofurans were hydrogenolyzed with insufficient AlH₂Cl.

  过量的AlH2Cl对2-芳氧基四氢呋喃的氢解反应，无论芳环上的取代基为何，都只产生预期的外向C-O键断裂产物，收率极高。没有检测到预期的环断裂产物4-芳氧基-1-丁醇。该反应比已知在相似条件下只产生环断裂产物的2-烷氧基四氢呋喃的AlH2Cl氢解反应要快得多。将2-芳氧基四氢呋喃或吡喃与AlCl3在醚中处理，会酸催化断裂为相应的酚和二氢呋喃或二氢吡喃，后者立即形成聚合物产物。对于那些芳环上没有取代基或芳环上带有电子给体基团的2-芳氧基四氢呋喃或吡喃，还会得到另一种产物，这种产物是由一个质子化的二氢呋喃或吡喃对酚的邻位或对位进行亲电攻击形成的。当2-芳氧基四氢呋喃与不足量的AlH2Cl氢解时，这些重排产物也会作为副产物产生，但数量很少。