2-氟-6-碘苯酚 | 28177-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-氟-6-碘苯酚
• 英文名称: 2-fluoro-6-iodophenol
• CAS: 28177-50-6
• 化学式: C₆H₄FIO
• 分子量: 238.0
• InChiKey: ZFARONFWYBCKDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2908199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-氟-6-碘苯酚 在 正丁基锂 、 氢氟酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.17h， 生成 5-Fluorobicyclo[4.2.0]octa-1(6),2,4-trien-7-one
  参考文献：
  名称：

  通过热和金属催化C的合并，RhI催化的苯丙基/ [7 + 1]环丙基苯并环丁烯与CO的环加成反应？C键解理

  摘要：

  已开发出Rh催化的环丙基-苯并环丁烯（CP-BCBs）和CO向苯并环辛烯酮的苯并/ [7 + 1]环加成反应。在该反应中，CP-BCB充当苯并/ 7-C合成子，该反应涉及两个CC键裂解：CP-BCB中四元环的热电环开环和Rh催化的C C环丙烷环的裂解。

  DOI：

  10.1002/chem.201405712
• 作为产物：
  描述：

  2-氟苯酚 在 盐酸 、 sodium hydroxide 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正戊烷 为溶剂， 反应 4.5h， 生成 2-氟-6-碘苯酚
  参考文献：
  名称：

  O-芳基N-异丙基氨基甲酸酯的定向邻锂化和异碘去甲硅烷基化反应合成卤代酚

  摘要：

  报道了通过原位 N-甲硅烷基化 O-芳基 N-异丙基氨基甲酸酯的直接邻位锂化反应区域选择性合成卤代酚。该协议由 C-甲硅烷基化氨基甲酸酯的 ipso-iododesilylation 反应和碘-镁交换反应补充，这些反应由相邻的氨基甲酰基团促进。这些方法提供了一系列 o-fluoro- 的入口。o-iodo- 和 oo'-diiodophenols 以其他方式难以获得的高产率。

  DOI：

  10.1055/s-2006-926462

文献信息

• MACROCYCLIC ANTAGONISTS OF THE MOTILIN RECEPTOR FOR TREATMENT OF GASTROINTESTINAL DYSMOTILITY DISORDERS
  申请人：Marsault Eric

  公开号：US20100093720A1

  公开（公告）日：2010-04-15

  The present invention provides conformationally-defined macrocyclic compounds that bind to and/or are functional modulators of the motilin receptor including subtypes, isoforms and/or variants thereof. These macrocyclic compounds, at a minimum, possess adequate pharmacological properties to be useful as therapeutics for a range of disease indications. In particular, these compounds are useful for treatment and prevention of disorders characterized by hypermotilinemia and/or gastrointestinal hypermotility, including, but not limited to, diarrhea, cancer treatment-related diarrhea, cancer-induced diarrhea, chemotherapy-induced diarrhea, radiation enteritis, radiation-induced diarrhea, stress-induced diarrhea, chronic diarrhea, AIDS-related diarrhea, C. difficile associated diarrhea, traveller's diarrhea, diarrhea induced by graph versus host disease, other types of diarrhea, dyspepsia, irritable bowel syndrome, chemotherapy-induced nausea and vomiting (emesis) and post-operative nausea and vomiting and functional gastrointestinal disorders. In addition, the compounds possess utility for the treatment of diseases and disorders characterized by poor stomach or intestinal absorption, such as short bowel syndrome, celiac disease and cachexia. The compounds also have use for the treatment of inflammatory diseases and disorders of the gastrointestinal tract, such as inflammatory bowel disease, ulcerative colitis, Crohn's disease and pancreatitis. Accordingly, methods of treating such disorders and pharmaceutical compositions including compounds of the present invention are also provided.

  本发明提供了与胃动素受体及其亚型、异构体和/或变体结合和/或是功能调节剂的构象定义明确的大环化合物。这些大环化合物至少具有足够的药理特性，可用作治疗一系列疾病指示的治疗药物。特别是，这些化合物对于治疗和预防以高胃动素血症和/或胃肠道高蠕动性为特征的疾病非常有用，包括但不限于腹泻、癌症治疗相关腹泻、癌症诱导腹泻、化疗诱导腹泻、放射性肠炎、放射性腹泻、压力诱导腹泻、慢性腹泻、艾滋病相关腹泻、C. difficile相关腹泻、旅行者腹泻、移植物宿主病引起的腹泻、其他类型的腹泻、消化不良、肠易激综合征、化疗诱导的恶心和呕吐（呕吐）以及术后恶心和呕吐和功能性胃肠道疾病。此外，这些化合物对于治疗以胃或肠道吸收不良为特征的疾病和疾病也具有用途，例如短肠综合征、乳糜泻和虚弱。这些化合物还可用于治疗胃肠道炎症性疾病和疾病，如炎症性肠病、溃疡性结肠炎、克罗恩病和胰腺炎。因此，本发明还提供了治疗此类疾病的方法和包括本发明化合物的药物组合物。
• Synthesis of 2-isoxazolyl-2,3-dihydrobenzofurans <i>via</i> palladium-catalyzed cascade cyclization of alkenyl ethers
  作者：Fei Zhou、Can Li、Meng Li、Yangbin Jin、Huanfeng Jiang、Yingjun Zhang、Wanqing Wu

  DOI：10.1039/d1cc00709b

  日期：——

  A novel palladium-catalyzed cascade cyclization reaction of alkenyl ethers with alkynyl oxime ethers for the construction of poly-heterocyclic scaffolds has been developed, in which the electron-rich alkene moiety functions as a three-atom unit, simultaneously dealing well with the coordination and regioselectivity of electron-rich olefins under metal catalysis. The strategy features excellent regio-

  开发了一种新型的钯催化的烯基醚与炔基肟肟的级联环化反应，以构建多杂环骨架，其中富电子的烯烃部分起三个原子单元的作用，同时很好地处理了配位和配位反应。金属催化下富电子烯烃的区域选择性。该策略具有出色的区域选择性和化学选择性以及良好的官能团耐受性。而且，新形成的2-异恶唑基-2,3-二氢苯并呋喃产物可以进一步转化为各种复杂的杂环，证明了它们在有机合成和药物化学中的潜在应用。
• Palladium-Catalyzed [3+3] Annulation of Vinyl Chromium(0) Carbene Complexes through Carbene Migratory Insertion/Tsuji-Trost Reaction
  作者：Kang Wang、Yifan Ping、Taiwei Chang、Jianbo Wang

  DOI：10.1002/anie.201707590

  日期：2017.10.9

  Vinyl chromium(0) Fischer carbene complexes were employed as the source of π‐allylic palladium species for catalytic [3+3] annulation under palladium catalysis. Mechanistically, this transformation is proposed to involve carbene migratory insertion and intramolecular Tsuji–Trost reaction as the key steps. Substituted six‐membered heterocyclic flavonones and quinolines are obtained, depending on the

  乙烯基铬（0）菲舍尔卡宾络合物被用作π烯丙基钯物质的来源，用于钯催化下的催化[3 + 3]环化。从机理上讲，这种转化被认为包括卡宾迁移插入和分子内Tsuji-Trost反应作为关键步骤。根据偶联伙伴上的亲核官能团，获得了取代的六元杂环黄酮和喹啉。
• Process for producing 1,2-dialkoxy-3-fluorobenzene
  申请人：Qiu Mingjian

  公开号：US20090227817A1

  公开（公告）日：2009-09-10

  The present invention relates to a process for producing a 2-fluoro-6-halophenol as an intermediate; a process for producing a 2-alkoxy-3-fluorophenol and further a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; a second process for producing a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; and a 2-alkoxy-3-fluorophenol. The 2-fluoro-6-halophenol can be obtained using a 2-fluorophenol as a starting material and through a sulfonation reaction, a halogenation reaction, and a deprotection reaction. The 2-fluoro-6-halophenol is alkyl-etherified, and subsequently the halogen atom is converted into a hydroxyl group to obtain the 2-alkoxy-3-fluorophenol, which is further alkyl-etherified to thereby obtain the 1,2-dialkoxy-3-fluorobenzene. Alternatively, a 1,2-dialkoxy-3-fluorobenzene is also obtained by converting the halogen atom of the 2-fluoro-6-halophenol into a hydroxyl group to thereby form 3-fluorocatechol and subsequently alkyl-etherifying two hydroxyl groups thereof. The processes of the invention realize low production costs and high process yields, and thus are suitable for industrial production of a 1,2-dialkoxy-3-fluorobenzene.

  本发明涉及一种生产2-氟-6-卤苯酚作为中间体的过程；一种从2-氟-6-卤苯酚生产2-烷氧基-3-氟苯酚，进而从中生产1,2-二烷氧基-3-氟苯的过程；一种从2-氟-6-卤苯酚生产1,2-二烷氧基-3-氟苯的第二过程；以及2-烷氧基-3-氟苯酚。可以使用2-氟苯酚作为起始原料，通过磺化反应、卤代反应和去保护反应获得2-氟-6-卤苯酚。将2-氟-6-卤苯酚烷基醚化，随后将卤原子转化为羟基以获得2-烷氧基-3-氟苯酚，进一步烷基醚化以获得1,2-二烷氧基-3-氟苯。另外，通过将2-氟-6-卤苯酚的卤原子转化为羟基从而形成3-氟邻苯二酚，随后烷基醚化两个羟基，也可以获得1,2-二烷氧基-3-氟苯。本发明的工艺实现了低生产成本和高工艺产率，因此适用于工业生产1,2-二烷氧基-3-氟苯。
• Halogen–lithium exchange between substituted dihalobenzenes and butyllithium: application to the regioselective synthesis of functionalized bromobenzaldehydes
  作者：Marek Dąbrowski、Joanna Kubicka、Sergiusz Luliński、Janusz Serwatowski

  DOI：10.1016/j.tet.2005.04.051

  日期：2005.7

  Halogen–lithium interconversion reactions between unsymmetrically substituted mono- and bifunctional dihalobenzenes C6H3XHal2 and C6H2XYHal2 (Hal=Br, I; X, Y=F, OR, CF3, CH(OMe)2) and butyllithium were investigated. The resultant organolithium intermediates were converted into the corresponding benzaldehydes in moderate to good yields. As a rule, bromine atoms in the position ortho to the functional group

  非对称取代的单官能和双官能二卤代苯C 6 H 3 XHal 2和C 6 H 2 XYHal 2之间的卤素-锂互变反应（Hal = Br，I； X，Y = F，OR，CF 3，CH（OMe）2）研究了丁基锂和丁基锂。将所得的有机锂中间体以中等至良好的产率转化成相应的苯甲醛。通常，邻位的溴原子官能团中的α优先被锂取代。具有双功能系统的分子内竞争实验表明，与甲氧基和二甲氧基甲基相比，氟能够更强地激活相邻的溴原子。用碘代替未活化的溴后，由于优选的碘-锂交换，可以完全逆转这种反应模式。