CN104262333A - 2-(丙烯-2-基)-2,3-二氢苯并呋喃-4-酚衍生物及其制备方法与应用 - Google Patents
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Abstract
本发明涉及化学结构式 Ⅰ 所示的2-(丙烯-2-基)-2,3-二氢苯并呋喃-4-酚衍生物:
Description
技术领域
本发明涉及一种新的化合物及其制备方法和应用,具体是2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物及其制备方法和应用。
背景技术
鱼藤酮是早期人们从鱼藤属等植物根部中提取分离出来的一种具有杀虫活性的化合物,是三大传统植物性杀虫剂之一 [杀虫植物与植物性杀虫剂. 第 2 版. 北京:中国农业出版社,2004]。由于鱼藤酮的杀虫谱广、残留期短、不易产生抗药性、对人畜安全和有利于促进生态平衡等优点,使得鱼藤酮作为绿色农药具有很大开发潜力 [中国植物性农药开发前景. 农药,2003,42(3):1]。中国发明专利描述了鱼藤酮衍生物的制备与应用[鱼藤酮肟醚及其制备方法和应用, ZL200810031441.2,2010.6.23授权;鱼藤酮肟烯/炔丙基醚及其作为杀虫剂的应用,ZL201110179503.6,2013.8.21授权;羧酸鱼藤酮肟酯及其制备方法与应用, ZL200810032173.6,2010.12.1授权;氨基甲酸鱼藤酮肟酯及其制备方法与应用, ZL200810031725.1,2010.10.6授权];中国发明专利也描述了鱼藤酮类似物的制备与应用[鱼藤环丙酰胺及其制备方法与应用,ZL201110226848.2,2013.3.20授权;N-酰基吡唑鱼藤醚及其制备方法与应用,ZL201010273525.4,2013.8.28授权;N-酰基吡唑鱼藤酚及其制备方法与应用, ZL201010273516.5,2013.9.4授权]。
中国发明专利描述了以鱼藤酮为原料合成一种结构新颖的环丙鱼藤酮,环丙鱼藤酮具有较好的抗肿瘤活性[环丙鱼藤酮及其制备方法与应用, ZL201010148043.6,2012.3.21授权]。
发明内容
本发明的目的在于提供了式Ⅰ所示的2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物:
Ⅰ
2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物化学名是 (2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚。2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物选自(R, 2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚、(S, 2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚或其非对映异构体的混合物:
。
本发明还提供了2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物的制备方法,其特征在于制备反应如下:
。
本发明还提供了式Ⅰ所示的化合物具有杀菌活性,可用于制备杀菌剂。
本发明与现有技术相比具有如下优点:首次制备了(2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚,其具有杀菌活性。
具体实施方式
以下实施例旨在说明本发明而不是对本发明的进一步限定。
实施例1
(2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚的制备:
2.00 g(4.90 mmol)环丙鱼藤酮,10 ml四氢呋喃,30℃下搅拌溶解,取0.28 g(7.4 mmol)硼氢化钠,分三次加入,TLC监测,50 min反应完全,反应液倒入200 ml水中,浓硫酸调pH至中性,抽滤,干燥得1.89 g (2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚,m.p. 85~87℃;1H NMR(400 MHz,CDCl3)δ:0.94~0.75(m,2H,C10H7O 1-H),1.04~0.95(m,1H,C10H7O 1a-H),1.77,1.78(2×s,3H,CH3),2.95~3.01(m,1H,C8H5O 3-H),3.38~3.27(m,1H,C8H5O 3-H),3.82,3.84(2×s,6H,2×OCH3),4.12~4.05(m,1H,C10H7O 2-H),4.19(d,J = 10.9 Hz,1H,C10H7O 2-H),4.91(s,1H,=CH2),5.09(s,1H,=CH2),5.25~5.17(m,1H,C8H5O 2-H),5.49(d,J = 10.9 Hz,1H,CH),6.34~6.28(m,1H,C10H7O 4-H),6.48(d,J = 4.3 Hz,1H,C8H5O 7-H),6.75(d,J = 8.1 Hz,1H,C10H7O 7-H),7.08(d,J = 4.3 Hz,1H,C8H5O 6-H),8.64,8.65(2×s,1H,4-OH)。
实施例2
(2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚的杀菌活性测定。
1 试验目的
在室内测定了新化合物在供试浓度下对各种病原菌的毒力,初步评价其杀菌活性。
2 试验条件
2.1供试靶标
油菜菌核病菌(Sclerotonia sclerotiorum),菌种均保存在冰箱(4-8℃)内,试验前2-3天从试管斜面接种到培养皿内,在适宜温度下培养供试验用。实验用培养基均为马铃薯琼脂培养基(PDA)。
2.2培养条件
供试靶标及试验后靶标的培养条件为温度25 ± 5℃,相对湿度65 ± 5%。
2.3仪器设备
烧杯、移液管、量筒、培养皿、高压灭菌锅、恒温生化培养箱等。
3 试验设计
3.1试验药剂
(2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚
。
3.2试验浓度
离体药剂浓度设25mg/L。
3.3药剂配制
原药:用万分之一电子天平称取所需量;溶剂:N,N-二甲基甲酰胺(DMF),0.2%;乳化剂:Tween 80,0.1%。
普筛测定:准确称取0.0500g样品,用0.20mLDMF溶解,加入含0.1% Tween80乳化剂的无菌水98.8ml,搅拌均匀,配制成500mg/L浓度溶液备用。
4 试验方法
参照《农药生物活性评价SOP》。
油菜菌核病菌:参照生测标准方法NY/T1156.2-2006,采用含药培养基法:取各500mg/L化合物药液2mL,加入冷却至45℃的38mL的PDA中,制成终浓度为25mg/L的含药培养基平板。然后从培养好的试验病菌菌落边缘取6.0mm直径菌丝块,移至含药培养基上,每处理4次重复。处理完毕,置于28℃的恒温生化培养箱中培养,4天后测量菌落直径,计算生长抑制率。
5 杀菌剂活性评价
处理后定期观察记录叶片、植株的发病情况和菌丝生长情况,根据病情指数和菌丝直径,计算防效和抑制率:
实验结果显示:在试验浓度25mg/L下,(2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚对油菜菌核病菌的抑制率为70.6%,活性良好,可以用于制备杀菌剂。
Claims (4)
1.化学结构式Ⅰ所示的2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物:
Ⅰ
2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物化学名是 (2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚。
2.权利要求1所述的2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物选自(R, 2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚、(S, 2R)-5-[(5,6-二甲氧基-1,1a,2,7b-四氢环丙并[c]苯并吡喃-7b-基) 羟甲基]- 2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚或其非对映异构体的混合物:
。
3. 权利要求1所述的2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物的制备方法,其特征在于它制备反应如下:
。
4. 权利要求1所述的2-(丙烯-2-基)-2, 3-二氢苯并呋喃-4-酚衍生物在制备杀菌核病菌的杀菌剂中的应用。
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CN112500421A (zh) * | 2020-12-15 | 2021-03-16 | 河南科技大学第一附属医院 | 一种可用于杀菌消毒的苯并吡喃脲类化合物的制备方法及应用 |
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CN112500421A (zh) * | 2020-12-15 | 2021-03-16 | 河南科技大学第一附属医院 | 一种可用于杀菌消毒的苯并吡喃脲类化合物的制备方法及应用 |
CN112500421B (zh) * | 2020-12-15 | 2021-08-24 | 河南科技大学第一附属医院 | 一种可用于杀菌消毒的苯并吡喃脲类化合物的制备方法及应用 |
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