6-methyl-4,5,6,7-tetrahydrobenzofuran-4-one | 157435-90-0

• 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: 6-methyl-4,5,6,7-tetrahydrobenzofuran-4-one
• 英文别名: 6-Methyl-6,7-dihydrobenzofuran-4(5H)-one；6-methyl-6,7-dihydro-5H-1-benzofuran-4-one
• CAS: 157435-90-0
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: ZHULAUSPJVAEMB-UHFFFAOYSA-N

物化性质

• 沸点：
  234.6±9.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  6-methyl-4,5,6,7-tetrahydrobenzofuran-4-one 、 氰基甲酸甲酯 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到methyl 4-oxo-6-methyl-4,5,6,7-tetrahydrobenzofuran-5-carboxylate
  参考文献：
  名称：

  Total Synthesis of Coriandrin

  摘要：

  Coriandrin, an antiviral agent, has been synthesized in nine steps from diketone 3. The key steps in the synthesis include an efficient aromatization reaction using N-bromosuccinimide and a palladium-mediated coupling of a benzylic bromide with a vinyl stannane.

  DOI：

  10.1021/jo00096a013
• 作为产物：
  描述：

  6-methyl-4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-2-yl acetate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以85%的产率得到6-methyl-4,5,6,7-tetrahydrobenzofuran-4-one
  参考文献：
  名称：

  AgBF4/[Bmim]BF4 催化的环状重氮二羰基化合物的 [3+2] 环加成：高效合成 2,3-二氢呋喃并转化为 3-酰基呋喃

  摘要：

  通过环状重氮二羰基化合物与苯乙烯和乙酸乙烯酯的反应，实现了一种新型高效的二氢呋喃环上具有多种取代基的 2,3-二氢呋喃的合成方法。关键策略是 AgBF/[Bmim]BF 催化的 [3+2] 环加成。合成的具有乙酸根的二氢呋喃进一步转化为相应的 3-酰基呋喃。

  DOI：

  10.5012/bkcs.2011.32.5.1554

文献信息

• Dipolar cycloaddition of rhodium carbenoids with vinyl esters. Total synthesis of pongamol and lanceolatin B
  作者：Michael C. Pirrung、Yong Rok Lee

  DOI：10.1016/s0040-4039(00)73399-5

  日期：1994.8

  A new method for dipolar cycloaddition of diazocyclohexane-1,3-diones, leading to benzofuran derivatives, has been applied to the total synthesis of natural products from Tephrosia and Pongamia.

  一种重氮偶氮环己烷-1,3-二酮偶极环加成反应的新方法，可产生苯并呋喃衍生物，已被用于全合成来自提弗罗西亚和庞加米的天然产物。
• WO2021009566A5
  申请人：——

  公开号：WO2021009566A5

  公开（公告）日：2023-07-25
• A new route for the synthesis of furanoflavone and furanochalcone natural products
  作者：Yong Rok Lee、Andrew T. Morehead

  DOI：10.1016/0040-4020(95)98689-f

  日期：1995.4

  An efficient synthesis of furanoflavones and furanochalcones has been carried out starting from a dihydrobenzofuran derivative.
• N-((1,2,3.5,6,7-HEXAHYDRO-S-INDACEN-4-YL)CARBAMOYL)-4, 5, 6, 7-TETRAHYDROBENZOFURAN -2-SULFONAMIDE DERIVATIVES AND RELATED COMPOUNDS AS NLPR3 MODULATORS FOR THE TREATMENT OF MULTIPLE SCLEROSIS (MS)
  申请人：Zomagen Biosciences Ltd

  公开号：US20220396559A1

  公开（公告）日：2022-12-15

  Described herein are N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl) carbamoyl)-4,5,6,7-tetrahydrobenzofuran-2-sulfonamide derivatives and related compounds of formula (I) wherein R1 is formulae (II), (III), (IV), (V), (VI), (VII), (VIII) or (IX) and R2 is formulae (X) or (XI) as NLPR3 (pyrin domain-containing protein 3) modulators for the treatment of e.g. metabolic diseases (e.g. type 2 diabetes or obesity), liver diseases (e.g. NAFLD or cirrhosis), lung diseases (e.g. asthma or CORD), central nervous system diseases (e.g. Alzheimer's disease or multiple sclerosis), inflammatory or autoimmune diseases (e.g. rheumatoid arthritis or psoriasis), cardiovascular diseases (e.g. atherosclerosis or stroke). The present description discloses the synthesis and characterisation of exemplary compounds as well as pharmacological data thereof (e.g. pages 67 to 90; examples 1 to 21; compounds 1 to 126; tables). An exemplary compound is e.g. N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)-4-hydroxy-4-methyl-4,5,6,7-tetrahydrobenzofuran-2-sulfonamide (Example 1; compound (5))
• [EN] N-((1,2,3,5,6,7-HEXAHYDRO-S-INDACEN-4-YL)CARBAMOYL)-4,5,6,7-TETRAHYDROBENZOFURAN -2-SULFONAMIDE DERIVATIVES AND RELATED COMPOUNDS AS NLPR3 MODULATORS FOR THE TREATMENT OF MULTIPLE SCLEROSIS (MS)<br/>[FR] DÉRIVÉS DE N-((1,2,3,5,6,7-HEXAHYDRO-S-INDACÈN-4-YL)CARBAMOYL)-4,5,6,7-TÉTRAHYDROBENZOFURAN -2-SULFONAMIDE ET COMPOSÉS APPARENTÉS EN TANT QUE MODULATEURS DE NLPR3 POUR LE TRAITEMENT DE LA SCLÉROSE EN PLAQUES (SEP)
  申请人：ZOMAGEN BIOSCIENCES LTD

  公开号：WO2021009566A1

  公开（公告）日：2021-01-21

  Described herein are N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl) carbamoyl)-4,5,6,7-tetrahydrobenzofuran-2-sulfonamide derivatives and related compounds of formula (I) wherein R1 is formulae (II), (III), (IV), (V), (VI), (VII), (VIII) or (IX) and R2 is formulae (X) or (XI) as NLPR3 ( pyrin domain-containing protein 3 ) modulators for the treatment of e.g. metabolic diseases (e.g. type 2 diabetes or obesity), liver diseases (e.g. NAFLD or cirrhosis), lung diseases (e.g. asthma or CORD), central nervous system diseases (e.g. Alzheimer's disease or multiple sclerosis), inflammatory or autoimmune diseases (e.g. rheumatoid arthritis or psoriasis), cardiovascular diseases (e.g. atherosclerosis or stroke). The present description discloses the synthesis and characterisation of exemplary compounds as well as pharmacological data thereof (e.g. pages 67 to 90; examples 1 to 21; compounds 1 to 126; tables). An exemplary compound is e.g. N-((1,2,3,5,6,7-hexahydro- s-indacen-4-yl)ca rba moyl)-4-hydroxy-4-methy 1-4, 5,6,7- tetrahydrobenzofuran-2-sulfonamide (Example 1; compound (5))