1-溴-2-甲氧基-6-(甲氧基甲氧基)苯 | 146746-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-溴-2-甲氧基-6-(甲氧基甲氧基)苯
• 英文名称: 1-bromo-2-methoxy-6-(methoxymethoxy)benzene
• 英文别名: 2-bromo-1-methoxy-3-(methoxymethoxy)benzene；1-methoxy-3-(methoxymethoxy)benzene；2-bromo-3-(methoxymethoxy)anisole
• CAS: 146746-58-9
• 化学式: C₉H₁₁BrO₃
• 分子量: 247.089
• InChiKey: WLRPBPWWBLSEOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  293.6±30.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-溴-2-甲氧基-6-(甲氧基甲氧基)苯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 生成
  参考文献：
  名称：

  Studies toward the Total Synthesis of Popolohuanone E:  Enantioselective Synthesis of 8-O-MethylpopolohuanoneE

  摘要：

  [GRAPHIC]8-O-Methylpopolohuanone E (2) was synthesized in a highly convergent manner starting from the cis-fused decalin derivative accessible from the (-)-Wieland-Miescher ketone analogue. The synthetic method features a biogenetic-type annulation of the phenolic and quinone segments to regioselectively construct the central tricyclic ring system as the key step.

  DOI：

  10.1021/ol016285h
• 作为产物：
  描述：

  1-甲氧基-3-(甲氧基甲氧基)苯 在 正丁基锂 、 Br₂C₂Cl₄ 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.25h， 以87%的产率得到1-溴-2-甲氧基-6-(甲氧基甲氧基)苯
  参考文献：
  名称：

  根据CN（R，S）策略进行螺环氨基苯并二氢吡喃衍生物的对映选择性合成。

  摘要：

  对映体纯的（3'R）-和（3'S）-3'，4'-二氢螺[哌啶-2,3'（2'H）-苯并吡喃] s（R）-10和（S）-10成功合成根据CN（R，S）方法进行研究，目的是作为产生相关螺环化合物的模式。从2-氰基-6-苯基恶唑并哌啶（-）-2开始研究了两种不同的合成途径。选择其中之一并分别用于从（-）-2和（+）-2开始制备胺（R）-17和（S）-17。使用β-环糊精作为手性选择剂，通过毛细管电泳确定所有最终氨基苯并二氢吡喃衍生物的对映体纯度。

  DOI：

  10.1021/jo026228h

文献信息

• Mechanistic aspects of asymmetric intramolecular Heck reaction involving dynamic kinetic resolution: flexible conformation of the cyclohexenylidene–benzene system
  作者：Shinzo Hosoi、Minoru Ozeki、Masashi Nakano、Kenji Arimitsu、Tetsuya Kajimoto、Naoto Kojima、Hiroki Iwasaki、Takuya Miura、Hiroyuki Kimura、Manabu Node、Masayuki Yamashita

  DOI：10.1016/j.tet.2015.01.020

  日期：2015.4

  An asymmetric intramolecular Heck reaction that involves the dynamic kinetic resolution of an atropisomer as the substrate furnished a product in high yield with high enantioselectivity. DFT calculations (Spartan'10, B3LYP/6-31G*) confirmed that the reaction proceeded via atropisomerization involving a conformational transformation (half-chair form/distorted-boat form) of the substrate.

  不对称的分子内Heck反应涉及阻转异构体的动态动力学拆分，因为底物以高收率和高对映选择性提供了产物。DFT计算（Spartan'10，B3LYP / 6-31G *）证实了该反应通过阻转异构化而进行，该异构化涉及底物的构象转化（半椅子形式/扭曲皿形式）。
• The Synthesis of<i>trans</i>-Flavan-3-ol Gallates by Regioselective Oxidative Etherification and Their Cytotoxicity Mediated by 67 LR
  作者：Nana Shiraishi、Motofumi Kumazoe、Shinichiro Fuse、Hirofumi Tachibana、Hiroshi Tanaka

  DOI：10.1002/chem.201602817

  日期：2016.9.5

  approach for the synthesis of trans‐flavan‐3‐ol gallates from epichlorohydrin. The trans‐flavan‐3‐ol gallates were prepared by the cycloetherification of the phenol at the C2 benzylic position of 2‐acylozyl‐1,3‐diarylpropane during regioselective C−H oxidation. The 1,3‐diarylpropanes were prepared starting from epichlorohydrin by epoxide opening with A and B ring precursors, followed by acylation of the resultant

  我们报告了一种从表氯醇合成反式黄烷-3-醇没食子酸酯的手性池方法。通过在区域选择性CH氧化过程中2-酰基唑基1,3-二芳基丙烷的C2苄基位置处的苯酚进行环醚化，可以制备反式-flavan-3-醇没食子酸酯。1,3-二芳基丙烷的制备是从环氧氯丙烷开始，先用A和B环前体进行环氧化物开环，然后用没食子酰氯酰化所得的醇。表氯醇的两种对映异构体均可用，因此可以使用相同的方法制备相应的对映异构体。测试了化合物对U266细胞的细胞毒性，其中5-脱氧-7,3'- O-没食子儿茶素没食子酸二甲酯的细胞毒性比天然（-）-EGCG强十倍以上。此外，衍生物的绝对构型不会严重影响生物学活性。
• An intramolecular arene-triflate coupling reaction for the regiospecific synthesis of substituted benzofluoranthenes
  作者：Joseph E. Rice、Zhen Wei Cai

  DOI：10.1021/jo00058a023

  日期：1993.3

  An intramolecular triflate-arene coupling reaction mediated by bis(triphenylphosphine)palladium(II) chloride has been developed for the synthesis of each of the isomeric benzofluoranthenes. This reaction, which results in formation of a new five-membered ring, proceeds in highest yield when performed using 0.1 equiv of the palladium catalyst, 3 equiv of lithium chloride, and 1.2 equiv of 1,8-diazabicyclo[5.4.0]undec-7-ene in N,N-dimethylformamide at 140-degrees-C. The biaryl precursors needed for the coupling reaction can be prepared by [1,2-bis(diphenylphosphino)ethane]nickel(II) chloride catalyzed coupling of an aryl bromide with an [o-(methoxymethoxy)aryl]magnesium bromide (prepared by ortho-lithiation of an aryl methoxymethyl ether followed by transmetalation with magnesium bromide). Using this procedure benzo[a]fluoranthene, benzo[b]fluoranthene, benzo[j]fluoranthene, and benzo[k]fluoranthene were prepared in yields of 84%, 85%, 93%, and 64%, respectively. The reaction to prepare benzo[j]fluoranthene was regiospecific and afforded none of the six-membered ring product, perylene. The method was extended to the preparation of benzo[b]fluoranthene (BbF) derivatives with fluoro or methoxy groups on the benzo ring. The cyclization of compounds possessing a methoxy group on the same ring as the triflate required the addition of 0.4 equiv of triphenylphosphine to the reaction mixture. Strategies are reported for the regiospecific preparation of 4-, 5-, 6-, and 7-substituted benzo[b]fluoranthenes. Evidence is presented which suggests the intermediacy of radicals in the oxidative-addition of aryl triflates to the palladium catalyst.
• Palladium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles via Enantioselective C–H Bond Functionalization
  作者：Ryo Shintani、Haruka Otomo、Kensuke Ota、Tamio Hayashi

  DOI：10.1021/ja302278s

  日期：2012.5.2

  A Pd-catalyzed asymmetric synthesis of Sistereogenic dibenzosiloles is developed through enantioselective C-H bond functionalization of prochiral 2-(arylsily)aryl triflates. High chemo- and enantioselectivities are achieved by employing a Josiphos-type ligand under mild conditions.