8-烯丙基-7-甲氧基香豆素 | 55136-74-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 8-烯丙基-7-甲氧基香豆素
• 英文名称: 8-allyl-7-methoxy-2H-chromen-2-one
• 英文别名: 8-allyl-7-methyloxycoumarin；7-methoxy-8-allylcoumarin；8-allyl-7-methoxycoumarin；8-allyl-7-methoxy-chromen-2-one；8-Allyl-7-methoxycumarin；7-methoxy-8-prop-2-enylchromen-2-one
• CAS: 55136-74-8
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: GSJJPFOIZRCDPP-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  371.0±42.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-烯丙基-7-甲氧基香豆素 在 吡啶盐酸盐 作用下， 反应 6.0h， 以47%的产率得到8-Methyl-8,9-dihydro-furo<2,3-h>chromen-2-on
  参考文献：
  名称：

  Mali; Manekar; Tilve, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 2, p. 113 - 116

  摘要：

  DOI：
• 作为产物：
  描述：

  7-羟基香豆素 在 potassium carbonate 、 potassium iodide 作用下， 以 乙二醇 、 丙酮 为溶剂， 反应 33.0h， 生成 8-烯丙基-7-甲氧基香豆素
  参考文献：
  名称：

  Synthesis and anthelmintic activity of osthol analogs against Dactylogyrus intermedius in goldfish

  摘要：

  In an attempt to develop novel anthelmintic agents, our previously isolated osthol was used as lead structures for further optimization. In our research, a series of coumarin analogs, prepared from 7-hydroxy coumarin or 7-hydroxy-4-methyl coumarin, have been evaluated for their anthelmintic activities. In all of the compounds, 6 and 7 were first synthesized, and their structures were identified based on NMR and MS values. Among the candidates, 8-allyl-7-allyloxycoumarin showed better anthelmintic activity than other compounds against Dactylogyrus infestation with EC50 value of 1.81 mg/L The quantitative structure-activity relationship (QSAR) of 16 osthol analogs with anthelmintic activity expressed as pEC(50) and toxicity to goldfish expressed pLC(50), such results can offer useful theoretical references for future experimental works. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.009

文献信息

• Synthesis of Allyl- and Prenylcoumarins via Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination
  作者：Bernd Schmidt、Martin Riemer

  DOI：10.1055/s-0035-1560501

  日期：——

  sequence of Claisen rearrangement, carbonyl olefination, and cyclization upon microwave irradiation in the presence of a stabilized ylide. The products are multiply substituted 6- or 8-allylated or prenylated coumarins (2H-chromen-2-ones). Allyl, dimethylallyl, crotyl, and prenyl ethers of various aromatic ortho-hydroxy carbonyl compounds undergo a tandem sequence of Claisen rearrangement, carbonyl olefination

  摘要 各种芳族邻羟基羰基化合物的烯丙基，二甲基烯丙基，巴豆基和异戊烯基醚在稳定的内酯存在下进行微波辐射后，会经历克莱森重排，羰基烯烃化和环化的串联序列。产物是被多重取代的6-或8-烯丙基化或烯丙基化的香豆素（2 H -chromen-2-ones）。 各种芳族邻羟基羰基化合物的烯丙基，二甲基烯丙基，巴豆基和异戊烯基醚在稳定的内酯存在下进行微波辐射后，会经历克莱森重排，羰基烯烃化和环化的串联序列。产物是被多重取代的6-或8-烯丙基化或烯丙基化的香豆素（2 H -chromen-2-ones）。
• Synthesis of linear coumarins via para-Claisen rearrangement of coumarate ester derivatives: total synthesis of suberosin, demethylsuberosin, and ostruthin
  作者：Nicholas Cairns、Laurence M. Harwood、David P. Astles

  DOI：10.1039/c39860001264

  日期：——

  Heating 2′-O-prenylated derivatives of 4′-O-benzyl methyl coumarates (3) furnishes the corresponding linear prenylated umbelliferones (1) directly via sequential para-Claisen rearrangement and relactonisation.

  加热4'- O-苄基香豆酸酯（3）的2'- O-烯丙基化衍生物（3），直接通过连续的对-克莱森重排和再内酯化作用提供相应的线性烯丙基化伞形酮（1）。
• Cobalt-Catalyzed Twofold Direct C(<i>sp</i> ² )−C(<i>sp</i> ³ ) Bond Coupling: Regioselective C-3 Alkylation of Coumarins with (Cyclo)alkyl Ethers
  作者：Longyang Dian、Hui Zhao、Daisy Zhang-Negrerie、Yunfei Du

  DOI：10.1002/adsc.201600349

  日期：2016.7.28

  A cobalt‐catalyzed regioselective C‐3 alkylation of coumarins was realized under mild reaction conditions, during which a variety of substituted coumarins including those containing sensitive functional groups could smoothly undergo the selective C(sp2)−C(sp3) bond formation with a series of cyclic or straight‐chain alkyl ethers.

  在温和的反应条件下实现了香豆素的钴催化区域选择性C-3烷基化，在此期间，包括具有敏感官能团的香豆素在内的各种取代的香豆素可以顺利地通过选择性C（sp 2）-C（sp 3）键形成一系列环状或直链烷基醚。
• Palladium-catalyzed synthesis of 8-allyl or 8-prenylcoumarins by using organotin reagents as multicoupling nucleophiles
  作者：Qiang Yin、Han Yan、Yaqin Zhang、Yige Wang、Guojin Zhang、Yuxiang He、Weihua Zhang

  DOI：10.1002/aoc.2944

  日期：2013.2

  In this study, 8‐iodocoumarin derivatives underwent a direct Stille cross‐coupling reaction with several organotin compounds in the presence of a catalytic amount of Pd(PPh3)4 in DMF at 80 °C. The cross‐coupling reaction proceeded smoothly under mild conditions and permitted the formation of 8‐allyl or 8‐prenylcoumarin compounds in good yields. Copyright © 2012 John Wiley & Sons, Ltd.

  在这项研究中，在80°C的DMF中催化量的Pd（PPh 3）4存在下，8-碘docoumarin衍生物与几种有机锡化合物直接进行了Stille交叉偶联反应。交叉偶联反应在温和条件下进行得很顺利，并以高收率形成了8个烯丙基或8个异戊烯基香豆素化合物。版权所有©2012 John Wiley＆Sons，Ltd.
• A novel class of inhibitors for steroid 5α-Reductase: synthesis and evaluation of umbelliferone derivatives
  作者：Gao-jun Fan、Woongchon Mar、Man Ki Park、Eun Wook Choi、Kinam Kim、Sanghee Kim

  DOI：10.1016/s0960-894x(01)00429-2

  日期：2001.9

  A series of umbelliferone derivatives was prepared and their 5alpha-reductase type 1 inhibitory activities were evaluated in cell culture systems. Our studies have identified a new series of potent 5alpha-reductase type 1 inhibitors and provided the basis for further development for the treatment of human endocrine disorders associated with overproduction of DHT by 5alpha-reductase type 1. The preliminary

  制备了一系列伞形酮衍生物，并在细胞培养系统中评估了它们的5α-还原酶1型抑制活性。我们的研究确定了一系列新的有效5α-还原酶1型抑制剂，并为进一步开发与5α-还原酶1型产生DHT相关的人类内分泌疾病提供了基础。初步的结构活性关系被描述为阐明基本的结构要求。