6-fluoro-3-methyl-chroman-4-one | 113209-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-fluoro-3-methyl-chroman-4-one
• 英文别名: 6-fluoro-2-methyl-4-chromanone；6-fluoro-3-methyl-4-chromanone；6-fluoro-3-methyl-2,3-dihydrochromen-4-one
• CAS: 113209-67-9
• 化学式: C₁₀H₉FO₂
• 分子量: 180.179
• InChiKey: CJEBXKSOAGIMIU-UHFFFAOYSA-N

物化性质

• 沸点：
  284.0±40.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-fluoro-3-methyl-chroman-4-one 在 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 (6-Fluoro-4-hydroxy-3-methyl-chroman-4-yl)-acetic acid
  参考文献：
  名称：

  乙内酰脲生物等排体。体内活性螺羟基乙酸醛糖还原酶抑制剂。

  摘要：

  醛糖还原酶抑制剂（ARI）山梨醇的临床副作用与其乙内酰脲环有关的假说导致了生物立体分析并用螺羟基乙酸部分取代乙内酰脲，如40所示。与乙内酰脲相比，这些羟酸在苯并二氢吡喃2-甲基取代时，效价增加相似，酸性与芳族部分的正交关系相似，ARI对映选择性也相似。在该系列中，六元螺羟基乙酸乙酸阴离子阵列是螺乙内酰脲阴离子的生物等排体，可导致ARI具有出色的体内活性。像第4步那样，通过苯并二氢吡喃-2-甲基化和通过芳香族6,7-卤素取代，使体外和体内活性提高了40倍以上。将大鼠体内具有最佳急性体内活性的化合物的慢性体内活性进行了比较。

  DOI：

  10.1021/jm00090a004
• 作为产物：
  描述：

  2-(allyloxy)-5-fluorobenzaldehyde 在 3-mesityl-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以57%的产率得到6-fluoro-3-methyl-chroman-4-one
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Hydroacylation of Unactivated Double Bonds

  摘要：

  An intramolecular N-heterocyclic carbene (NHC)-catalyzed hydroacylation of unactivated double bonds is reported. Systematic variation of the catalyst structure revealed an N-mesitylthiazolylidene annulated with a seven-membered ring to be especially reactive. This NHC enables a unique C-C bond-forming reaction to afford substituted chroman-4-ones in moderate to excellent yields, even ones containing all-carbon quaternary centers.

  DOI：

  10.1021/ja906361g

文献信息

• [EN] MGLUR7 AGONIST COMPOUNDS FOR TREATING MGLUR7- REGULATED DISEASES, DISORDERS, OR CONDITIONS<br/>[FR] COMPOSÉS AGONISTES DE MGLUR7 POUR LE TRAITEMENT DE MALADIES, TROUBLES OU ÉTATS RÉGULÉS PAR MGLUR7
  申请人：TAKEDA PHARMACEUTICALS CO

  公开号：WO2018092921A1

  公开（公告）日：2018-05-24

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof wherein Z, R1, R2, R3, R4, R5 and R6 are as defined in the specification, a process for their preparation, pharmaceutical compositions containing them and their use in therapy. The present invention further provides methods of treating at least one disease, disorder, or condition associated with the glutamatergic and GABAergic signalling pathways regulated in full or in part by metabotropic glutamate receptor 7 (mGluR7) by administering a compound of formula (I) or a pharmaceutically acceptable salt thereof to a subject. The compound may be a selective agonist of mGluR7, which modulates the release of at least one neurotransmitter in the subject.

  本发明提供了式(I)的化合物及其药用盐，其中Z、R1、R2、R3、R4、R5和R6如规范中定义，以及它们的制备方法，含有它们的药物组合物以及它们在治疗中的用途。本发明还提供了治疗至少一种与谷氨酸能和GABA能信号通路相关的疾病、紊乱或症状的方法，该信号通路完全或部分由代谢型谷氨酸受体7（mGluR7）调节，通过向受试者投药式(I)的化合物或其药用盐。该化合物可能是mGluR7的选择性激动剂，调节受试者中至少一种神经递质的释放。
• Preparation of 6-substituted 4-chromanones
  申请人：Mallinckrodt Inc.

  公开号：US04918203A1

  公开（公告）日：1990-04-17

  Disclosed is a practical and efficient process for preparing 6-substituted 4-chromanones from phenolic acrylate ester compounds derivable from para-substituted phenolic or thiophenolic compounds and beta-unsubstituted acrylic acid compounds which are esterifiable therewith. The process includes effecting rearrangement of a phenolic or thiophenolic acrylate ester in the presence of a rearrangement effective amount of hydrogen fluoride to the corresponding hydroxy - or mercapto (vinyl ketone) wherein the carbonyl carbon atom of the vinyl carboxy group is directly attached to the benzene ring ortho to the hydroxy or mercapto group. Thereafter, the vinyl ketone is cyclized to the corresponding 6-substituted 4-chromanone in the presence of a cyclization-effective amount of hydrogen fluoride. The 6-substituted 4-chromanones prepared by the process are useful as intermediates for preparing pharmaceutical agents.

  本公开了一种从可由对位取代酚或噻吩酚化合物和可与之酯化的β-未取代丙烯酸化合物制备6-取代的4-色酮的实用高效方法。该方法包括在氢氟酸的存在下使酚或噻吩酚丙烯酸酯发生重排，形成对应的羟基或巯基（乙烯酮），其中乙烯羧基的羰基碳原子直接连接到苯环邻位的羟基或巯基。然后，在氢氟酸的存在下，乙烯酮被环化成相应的6-取代的4-色酮，生成环化效果的氢氟酸量。通过该方法制备的6-取代的4-色酮可用作制备药物代理的中间体。
• 플러렌 유도체, 이를 이용한 유기 태양 전지 및 이의 제조 방법
  申请人：LG CHEM, LTD. 주식회사 엘지화학(120010134563) Corp. No ▼ 110111-2207995BRN ▼107-81-98139

  公开号：KR20150092724A

  公开（公告）日：2015-08-13

  본 명세서는 플러렌 유도체, 이를 포함하는 유기 태양 전지 및 이의 제조 방법에 관한 것이다.

  本规范书涉及有机太阳能电池，包括其中包含的花菲催化剂以及其制造方法。
• Synthesis of 3,3‐Dimethyl‐4‐chromanones: Improved Procedures Without Ring Opening
  作者：Ayako Yamashita、Emily B. Norton、Cilien Hanna、Jaechul Shim、Edward J. Salaski、Dahui Zhou、Tarek S. Mansour

  DOI：10.1080/00397910500383543

  日期：2006.3.1

  Abstract A procedure for the 3,3‐dimethylation of 4‐chromanones under basic conditions was improved; the by‐product from chromanone ring opening was isolated and its structure was determined.

  摘要 改进了碱性条件下 4-色满酮的 3,3-二甲基化工艺；分离出色满酮开环的副产物并确定其结构。
• [EN] SUBSTITUTED SULFONAMIDE-CHROMAN COMPOUNDS, AND PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE SULFONAMIDE-CHROMANE SUBSTITUÉS, COMPOSITIONS PHARMACEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SUNOVION PHARMACEUTICALS INC

  公开号：WO2022217248A1

  公开（公告）日：2022-10-13

  Provided herein are compounds, pharmaceutical compositions, and methods of use thereof, including methods of treating neurological disorders. For example, provided herein is a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein values for the variables (e.g., X1, R1A, R1B, R2A, R2B, R3A, R3B, R3C, R3D) are as disclosed herein. The compounds disclosed herein (e.g., compounds of Formula I, or pharmaceutically acceptable salts thereof) and pharmaceutical compositions can be used to treat neurological disorders.

  本文提供了化合物、药物组合物及其使用方法，包括治疗神经系统疾病的方法。例如，本文提供了公式I的化合物或其药学上可接受的盐，其中变量的值（例如X1、R1A、R1B、R2A、R2B、R3A、R3B、R3C、R3D）如本文所披露。本文披露的化合物（例如公式I的化合物或其药学上可接受的盐）和药物组合物可用于治疗神经系统疾病。