(±)-7-(1,3-benzodioxol-5-yl)-furo[3,4-b]pyridine-5(7H)-one | 1438281-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (±)-7-(1,3-benzodioxol-5-yl)-furo[3,4-b]pyridine-5(7H)-one
• 英文别名: 7-(benzo[d][1,3]dioxol-5-yl)furo[3,4-b]pyridin-5(7H)-one；7-(1,3-benzodioxol-5-yl)-7H-furo[3,4-b]pyridin-5-one
• CAS: 1438281-41-4
• 化学式: C₁₄H₉NO₄
• 分子量: 255.23
• InChiKey: RGCZQTXLMXDTPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  胡椒醛 、 2-碘吡啶-3-羧酸乙酯 在 lithium chloro-isopropyl-magnesium chloride 、 甲醇 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以83%的产率得到(±)-7-(1,3-benzodioxol-5-yl)-furo[3,4-b]pyridine-5(7H)-one
  参考文献：
  名称：

  A concise synthesis of 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4- b ]pyridin-5(7 H )-ones], 3-aryl-, and alkylphthalides

  摘要：

  A synthetically useful protocol has been developed for the preparation of highly functionalized 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4-b]pyridin-5(7H)-ones], 3-aryl-, and alkylphthalides. Reaction of 2-iodobenzoate esters and 2-iodopyridine carboxylate esters with i-PrMgCl center dot LiCl in the presence of cyclic ketones under standard Barbier reaction conditions affords 3,4-fused spiro[isobenzofuran-3-ones] and spiro[furo[3,4-b]pyridin-5(7H)-ones] in good to excellent yields. Step-wise addition of i-PrMgCl center dot LiCl to 2-iodobenzoate esters followed by trapping with various aldehydes yields 3-aryl and 3-alkylphthalides; whereas, under similar conditions access to 3-aryl and 3-alylazaphthalides is also possible. Extension of this methodology toward the preparation of 3-n-butylphthalide and chrycolide, a natural product isolated from the leaves and stems of Chrysanthemum coronarium, is also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.051

文献信息

• Organometallic Reagents: Efficient Tools for the Synthesis of Fused Pyridinyl‐Lactones
  作者：Lynda Hammas、Sabrina Touchet、Sandrine Adach、Corinne Comoy

  DOI：10.1002/ejoc.202300800

  日期：2023.11.14

  Through the development of a one pot synthesis of fused substituted heteroaryl-lactones involving a Metal/Halogen Exchange reaction as key step, the reactivity of various mono- or bimetallic reagents (organolithiums, Grignard reagents and lithium organomagnesiate complexes) was explored to aim high chemoselectivity and efficiency starting from sensitive substrates.

  通过开发以金属/卤素交换反应为关键步骤的稠合取代杂芳基内酯的一锅合成，探索了各种单金属或双金属试剂（有机锂、格氏试剂和有机镁酸锂络合物）的反应性，以实现高化学选择性和效率从敏感基材开始。
• BENZO AND PYRIDO PYRIDAZINONE AND PYRIDAZINTHIONE COMPOUNDS WITH PDE IV INHIBITING ACTIVITY
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0612321A1

  公开（公告）日：1994-08-31
• [EN] BENZO AND PYRIDO PYRIDAZINONE AND PYRIDAZINTHIONE COMPOUNDS WITH PDE IV INHIBITING ACTIVITY
  申请人：SYNTEX (U.S.A.) INC.

  公开号：WO1993007146A1

  公开（公告）日：1993-04-15

  (EN) Benzo or pyridopyridazinones and pyridazinthiones of formula (I) wherein: X and Y are nitrogen or carbon, provided that at least one is carbon, and Z is oxygen or sulfur; R1 is hydrogen, lower alkyl, aryl, heteroaryl, or heterocycle lower alkylene; R2, R3, R4, R5 and R6 are independently selected from hydrogen, lower alkyl, halo, carboxy, alkoxycarbonyl, carbamoyl, acyl, acyl halide, thiomethyl, trifluoromethyl, cyano or nitro; or a pharmaceutically acceptable ester, ether or salt thereof, have been found to be useful as an anti-inflammatory, antiasthmatic, immunosuppressive, anti-allograft rejection, anti-graft-vs-host rejection, autoimmune disease or analgetic agent(s).(FR) Benzo ou pyrido pyridazinones et pyridazinthiones de la formule (I) dans laquelle X et Y représentent azote ou carbone, à condition qu'au moins l'un des deux représente du carbone, et Z représente oxygène ou soufre; R1 représente hydrogène, alkyle inférieur, aryle, hétéroaryle ou alkylène inférieur à hétérocycles; R2, R3, R4, R5 et R6 sont sélectionnés indépendamment parmi hydrogène, alkyle inférieur, halo, carboxy, alcoxycarbonyle, carbamoyle, acyle, halogénure d'acyle, thiométhyle, trifluorométhyle, cyano ou nitro; ou un ester, éther ou sel pharmaceutiquement acceptable desdits composés. On a découvert que les composés de l'invention sont utiles comme agents anti-inflammatoires, anti-asthmatiques, immunosuppresseurs, anti-rejet d'halogreffes, anti-rejet de greffes par un hôte, contre les maladies auto-immunes ou analgésiques.