2-allyl-6-methoxybenzene-1,4-diol | 31788-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-allyl-6-methoxybenzene-1,4-diol
• 英文别名: 2-Methoxy-6-(prop-2-en-1-yl)benzene-1,4-diol；2-methoxy-6-prop-2-enylbenzene-1,4-diol
• CAS: 31788-39-3
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: ZIWAQBRTNFYVGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-allyl-6-methoxybenzene-1,4-diol 在 (R)-(3,3'-bis(1-naphthyl)-1,1'-binaphthanele-2,2'-yl)phosphoric acid 、 rhodium(III) chloride trihydrate 、 三(五氟苯基)硼烷 、 三溴化硼 、 三甲基氢氧化锡 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 53.5h， 生成 (+)-fumimycin
  参考文献：
  名称：

  （+）-和（-）-泛霉素的简洁和收敛的对映体全合成

  摘要：

  通过利用高取代氢醌和相应脱氢丙氨酸生成的N-富芳基酮亚胺的不对称aza-Friedel-Crafts反应策略，可以实现（+）-和（-）-富霉素的简洁且收敛的总合成。对映体纯天然产物及其对映体通过使用BINOL衍生的手性磷酸（CPA）催化剂的两种对映体，以七个步骤和22％的总收率制备。

  DOI：

  10.1021/acs.joc.9b02020
• 作为产物：
  描述：

  4-(烯丙氧基)-3-甲氧基苯甲醛 在 二苯硒醚 、 双氧水 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 2-allyl-6-methoxybenzene-1,4-diol
  参考文献：
  名称：

  （+）-和（-）-泛霉素的简洁和收敛的对映体全合成

  摘要：

  通过利用高取代氢醌和相应脱氢丙氨酸生成的N-富芳基酮亚胺的不对称aza-Friedel-Crafts反应策略，可以实现（+）-和（-）-富霉素的简洁且收敛的总合成。对映体纯天然产物及其对映体通过使用BINOL衍生的手性磷酸（CPA）催化剂的两种对映体，以七个步骤和22％的总收率制备。

  DOI：

  10.1021/acs.joc.9b02020

文献信息

• Synthesis of Methoxyfumimycin with 1,2-Addition to Ketimines
  作者：Patrick J. Gross、Caroline E. Hartmann、Martin Nieger、Stefan Bräse

  DOI：10.1021/jo902026s

  日期：2010.1.1

  The synthesis of (±)-methoxyfumimycin, a potential new bacterial peptide deformylase (PDF) inhibitor, is reported. To generate the stereogenic fully substituted carbon, the key step is a 1,2-addition of a methyl Grignard reagent to a ketimine. The overall synthetic strategy involves a Dakin oxidation of a vanillin derivative, Friedel−Crafts acylation, Claisen rearrangement, lactonization, and rhodium-catalyzed

  据报道，（±）-甲氧基泛霉素是一种潜在的新型细菌肽去甲酰基酶（PDF）抑制剂的合成。为了产生立体生成的完全取代的碳，关键步骤是将甲基格氏试剂1,2-添加到酮亚胺上。总体合成策略涉及香兰素衍生物的Dakin氧化，Friedel-Crafts酰化，克莱森重排，内酯化和铑催化的烯烃异构化。
• Feeding-deterrent activity of ?-asarone isomers against some stored Coleoptera
  作者：Janusz Pop?awski、Bo?ena ?ozowicka、Alina T Dubis、Barbara Lachowska、Zbigiew Winiecki、Jan Nawrot

  DOI：10.1002/(sici)1526-4998(200006)56:6<560::aid-ps171>3.0.co;2-x

  日期：2000.6

  All isomers of alpha-asarone [(E)-4-prop-1-enyl-1,2,5-trimethoxybenze] were tested for their feeding deterrent activity against adults of Sitophilus granarius and Tribolium confusum and larvae of Trogoderma granarium and Tribolium confusum. (E)-2-prop-1-enyl-1,3, 5-trimethoxybenzene exhibited the strongest deterrent activity against all the species tested. The total coefficients of deterrency for this compound were 140.6 and 169.7 for Tribolium confusum adults and larvae, respectively, and 144.9 and 104.6 for larvae of Trogoderma granarium and adults of Sitophilus granarius, respectively. (C) 2000 Society of Chemical Industry.
• Synthesis and Hypolipidemic and Antiplatelet Activities of α-Asarone Isomers in Humans (in Vitro), Mice (in Vivo), and Rats (in Vivo)
  作者：Janusz Popławski、Bożena Łozowicka、Alina T. Dubis、Barbara Lachowska、Stanisław Witkowski、Danuta Siluk、Jacek Petrusewicz、Roman Kaliszan、Jacek Cybulski、Małgorzata Strzałkowska、Zdzisław Chilmonczyk

  DOI：10.1021/jm000905n

  日期：2000.10.1

  yA series of alpha-asarone isomers was synthesized and investigated for their hypolipidemic and antiplatelet activity. Considering the hypolipidemic activity in rats at a dose of 80 mg/kg/day, some isomers were more potent than clofibrate at 150 mg/kg. Compound 3 was one of the most active agents elevating the HDL cholesterol level by 56% and lowering the LDL cholesterol level by 46.8% in rats after 7 days of administration. The activities of the platelet aggregation test in vitro were significant but lower than those of the reference substances (indomethacine and acetylsalicylic add). In the pulmonary thromboembolic in vivo test in mice, two compounds (alpha-asarone (6) and compound 4) produced significant anti thrombotic effects at 100 mg/kg, namely 44% and 52% protection against lung microembolia, respectively. alpha-Asarone derivatives form a new group of potential hypolipidemic and/or antithrombotic agents. The compounds 3, 4, and 6 may serve as lead substances whose structural modifications may result in original drugs.
• Wolska; Poplawski; Lozowicka, Polish Journal of Chemistry, 1998, vol. 72, # 10, p. 2331 - 2341
  作者：Wolska、Poplawski、Lozowicka

  DOI：——

  日期：——
• Bi(OTf)3-catalyzed allylation of quinones with allyltrimethylsilane
  作者：J.S Yadav、B.V.S Reddy、T Swamy

  DOI：10.1016/s0040-4039(03)01130-4

  日期：2003.6

  p-Quinones react smoothly with allyltrimethylsilane in the presence of 2 mol%, of Bi(OTf)(3) under mild reaction conditions to afford the corresponding allyl substituted benzene derivatives, p-allylquinols and allyl substituted 1,4-naphthoquinones in excellent yields with high regioselectivity. This method is very useful for the direct introduction of an allyl functionality onto a quinone moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.