2,2,7-trimethyl-1-benzofuran-3(2H)-one | 126224-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2,2,7-trimethyl-1-benzofuran-3(2H)-one
• 英文别名: 2,2,7-trimethyl-benzofuran-3-one；2,2,7-Trimethyl-benzofuran-3-on；2,2,7-Trimethyl-1-benzofuran-3-one
• CAS: 126224-37-1
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: SAYHBUQZHPWWJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,7-trimethyl-1-benzofuran-3(2H)-one 、 1,2-乙二硫醇 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以100%的产率得到2,2,7-trimethylspiro[1-benzofuran-3,2'-[1,3]dithiolane]
  参考文献：
  名称：

  Increasing Selectivity of CC Chemokine Receptor 8 Antagonists by Engineering Nondesolvation Related Interactions with the Intended and Off-Target Binding Sites

  摘要：

  The metabolic stability and selectivity of a series of CCR8 antagonists against binding to the hERG ion channel and cytochrome Cyp2D6 are studied by principal component analysis. It is demonstrated that an efficient way of increasing metabolic stability and selectivity of this series is to decrease compound lipophilicity by engineering nondesolvation related attractive interactions with CCR8, as rationalized by three-dimensional receptor models. Although Such polar interactions led to increased compound selectivity, such a strategy could also jeopardize the DMPK profile of compounds. However, once increased potency is found, the lipophilicity can be readjusted by engineering hydrophobic substituents that fit to CCR8 but do not fit to hERG. Several such lipophilic fragments are identified by two-dimensional fragment-based QSAR analysis. Electrophysiological measurements and site-directed mutagenesis studies indicated that the repulsive interactions of these fragments with hERG are caused by steric hindrances with residue F656.

  DOI：

  10.1021/jm900713y
• 作为产物：
  描述：

  2-methyl-2-(2-methylphenoxy)propionyl chloride 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以42%的产率得到2,2,7-trimethyl-1-benzofuran-3(2H)-one
  参考文献：
  名称：

  Increasing Selectivity of CC Chemokine Receptor 8 Antagonists by Engineering Nondesolvation Related Interactions with the Intended and Off-Target Binding Sites

  摘要：

  The metabolic stability and selectivity of a series of CCR8 antagonists against binding to the hERG ion channel and cytochrome Cyp2D6 are studied by principal component analysis. It is demonstrated that an efficient way of increasing metabolic stability and selectivity of this series is to decrease compound lipophilicity by engineering nondesolvation related attractive interactions with CCR8, as rationalized by three-dimensional receptor models. Although Such polar interactions led to increased compound selectivity, such a strategy could also jeopardize the DMPK profile of compounds. However, once increased potency is found, the lipophilicity can be readjusted by engineering hydrophobic substituents that fit to CCR8 but do not fit to hERG. Several such lipophilic fragments are identified by two-dimensional fragment-based QSAR analysis. Electrophysiological measurements and site-directed mutagenesis studies indicated that the repulsive interactions of these fragments with hERG are caused by steric hindrances with residue F656.

  DOI：

  10.1021/jm900713y

文献信息

• Resorcine Derivatives and Their Use as Pesticides
  申请人：Puhl Michael

  公开号：US20090209598A1

  公开（公告）日：2009-08-20

  This invention relates to resorcine derivatives of formula (I) wherein R 1 is phenyl or a 5- to 6-membered heteroaromatic ring which may contain 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur, wherein phenyl or the heteroaromatic ring may be fused to a ring selected from phenyl and a 5- to 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which may contain 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur, wherein phenyl or the 5- to 6-membered heteroaromatic ring or the respective fused ring systems may be unsubstituted or substituted by any combination of 1 to 6 optionally substituted groups R 3 , wherein R 3 is halogen, cyano, nitro, hydroxy, mercapto, amino, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, halocycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, alkylthio, alkenylthio, alkynylthio, haloalkylthio, haloalkenylthio, haloalkynylthio, alkylamino, alkenylamino, alkynylamino, dialkylamino, dialkenylamino, dialkynylamino, alkyl-alkenylamino, alkyl-alkynylamino, alkenyl-alkynylamino, trialkylsilyl, or phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which may contain 1 to 3 heteroatoms selected from oxygen, sulfur and nitrogen or a 5- to 6-membered heteraromatic ring system which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur, which phenyl and which heteroaromatic ring may be bonded via an oxygen or a sulfur atom, or —C(=G)Ra, —C(=G)ORa, —C(=G)NRa2, —C(=G)[N═SRa2], —C(═NORa)Ra, —C(═NORa)NRa2, —C(═NNRa2)Ra, —OC(=G)-OC(=G)ORa, N═SRa2, —NRaC(=G)Ra, —N[C(=G)Ra]2, —NRaC(=G)ORa, —C(=G)NRa—NRa2, —C(=G)NRa—NRa[C(=G)Ra], —NRa—C(=G)NRa2, —NRa—NRaC(=G)Ra, —NRa—N[C(=G)Ra]2, —N[(C=G)Ra]—NRa2, —NRa—NRa[(C=G)GRa], —NRa[(C=G)NRa2, —NRa[C═NRa]Ra, —NRa(C═NRa)NRa2, —O—NRa2, —O—NRa(C=G)Ra, —SO2NRa2, —NRaSO2Ra, —S(═O)Ra, —S(═O)2Ra, —SO2ORa, or —OSO2Ra, wherein G is oxygen or sulfur and Ra is as defined in the description, R 2 is hydrogen, halogen, cyano, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, or haloalkoxy, x is 2, 3, 4, 5, 6, or 7, or the diastereomers, enantiomers, salts or N-oxides thereof, with the proviso that R 1 is not 5-chloro-2,2,-dimethyl-2,3-dihydrobenzo[b]furan-7-yl when R 2 is hydrogen and x is 3 or 4, processes and intermediates for the preparation of compounds I, use of compounds I for combating insects, acarids, or nematodes, and a method for treating, controlling, preventing or protecting animals against infestation or infection by parasites using compounds I.

  本发明涉及公式（I）的间苯二酚衍生物，其中R1是苯基或5-至6-成员杂芳环，可以包含1至3个从氧、氮和硫选择的杂原子，其中苯基或杂芳环可以与从苯基和5-至6-成员饱和、部分不饱和或芳香杂环环中选择的环融合，该环可以包含1至3个从氧、氮和硫选择的杂原子，其中苯基或5-至6-成员杂芳环或相应的融合环系统可以是未取代或由1至6个可选取代基团R3的任意组合取代，其中R3是卤素、氰基、硝基、羟基、巯基、氨基、烷基、烯基、炔基、环烷基、环烯基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、卤代环烯基、烷氧基、烯氧基、炔氧基、卤代烷氧基、卤代烯氧基、卤代炔氧基、烷硫基、烯硫基、炔硫基、卤代烷硫基、卤代烯硫基、卤代炔硫基、烷基氨基、烯基氨基、炔基氨基、二烷基氨基、二烯基氨基、二炔基氨基、烷基-烯基氨基、烷基-炔基氨基、烯基-炔基氨基、三烷基硅基、苯基或5-至7-成员饱和或部分不饱和杂环环，可以包含1至3个从氧、硫和氮选择的杂原子或可以包含1至4个从氧、氮和硫选择的杂原子的5-至6-成员杂芳环系统，其中苯基和杂芳环可以通过氧或硫原子连接，或-C（=G）Ra、-C（=G）ORa、-C（=G）NRa2、-C（=G）[N═SRa2]、-C（═NORa）Ra、-C（═NORa）NRa2、-C（═NNRa2）Ra、-OC（=G）-OC（=G）ORa、N═SRa2、-NRaC（=G）Ra、-N[C（=G）Ra]2、-NRaC（=G）ORa、-C（=G）NRa-NRa2、-C（=G）NRa-NRa[C（=G）Ra]、-NRa-C（=G）NRa2、-NRa-NRaC（=G）Ra、-NRa-N[C（=G）Ra]2、-N[(C=G）Ra]-NRa2、-NRa-NRa[(C=G）GRa]、-NRa[(C=G）NRa2、-NRa[C═NRa]Ra、-NRa（C═NRa）NRa2、-O-NRa2、-O-NRa（C=G）Ra、-SO2NRa2、-NRaSO2Ra、-S（═O）Ra、-S（═O）2Ra、-SO2ORa或-OSO2Ra，其中G是氧或硫，Ra如描述中所定义，R2是氢、卤素、氰基、烷基、卤代烷基、烯基、卤代烯基、炔基、卤代炔基、烷氧基或卤代烷氧基，x是2、3、4、5、6或7，或其对映异构体、对映体、盐或N-氧化物，但在R2为氢且x为3或4时，R1不是5-氯-2,2-二甲基-2,3-二氢苯并[b]呋喃-7-基，制备化合物I的过程和中间体，使用化合物I对抗昆虫、螨虫或线虫，以及使用化合物I治疗、控制、预防或保护动物免受寄生虫的侵害或感染的方法。
• KITAZAWA, MAKIO;AKAHANE, MASUO;NAKANO, YASUSHI;HAYAKAWA, KAZUHIDE;SATO, K+, YAKUGAKU DZASSI, 109,(1989) N0, S. 718-736
  作者：KITAZAWA, MAKIO、AKAHANE, MASUO、NAKANO, YASUSHI、HAYAKAWA, KAZUHIDE、SATO, K+

  DOI：——

  日期：——
• Increasing Selectivity of CC Chemokine Receptor 8 Antagonists by Engineering Nondesolvation Related Interactions with the Intended and Off-Target Binding Sites
  作者：Igor Shamovsky、Chris de Graaf、Lisa Alderin、Malena Bengtsson、Håkan Bladh、Lena Börjesson、Stephen Connolly、Hazel J. Dyke、Marco van den Heuvel、Henrik Johansson、Bo-Göran Josefsson、Anna Kristoffersson、Tero Linnanen、Annea Lisius、Roope Männikkö、Bo Nordén、Steve Price、Lena Ripa、Didier Rognan、Alexander Rosendahl、Marco Skrinjar、Klaus Urbahns

  DOI：10.1021/jm900713y

  日期：2009.12.10

  The metabolic stability and selectivity of a series of CCR8 antagonists against binding to the hERG ion channel and cytochrome Cyp2D6 are studied by principal component analysis. It is demonstrated that an efficient way of increasing metabolic stability and selectivity of this series is to decrease compound lipophilicity by engineering nondesolvation related attractive interactions with CCR8, as rationalized by three-dimensional receptor models. Although Such polar interactions led to increased compound selectivity, such a strategy could also jeopardize the DMPK profile of compounds. However, once increased potency is found, the lipophilicity can be readjusted by engineering hydrophobic substituents that fit to CCR8 but do not fit to hERG. Several such lipophilic fragments are identified by two-dimensional fragment-based QSAR analysis. Electrophysiological measurements and site-directed mutagenesis studies indicated that the repulsive interactions of these fragments with hERG are caused by steric hindrances with residue F656.