1-[5-[(4-氟苯基)甲基]呋喃-2-基]乙酮 | 280571-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[5-[(4-氟苯基)甲基]呋喃-2-基]乙酮
• 英文名称: 2-acetyl-5-(4-fluorobenzyl)-furan
• 英文别名: 1-(5-(4-fluorobenzyl)furan-2-yl)ethanone；5-(4-fluorobenzyl)-2-furyl methyl ketone；2-acetyl-5-(4-fluorobenzyl)furan；2-acetyl-5(4-fluorobenzyl)furan；1-[5-[(4-Fluorophenyl)methyl]furan-2-yl]ethanone
• CAS: 280571-34-8
• 化学式: C₁₃H₁₁FO₂
• 分子量: 218.228
• InChiKey: KJMDYHQKWUHDLU-UHFFFAOYSA-N

物化性质

• 熔点：
  28 °C
• 沸点：
  334.9±37.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[5-[(4-氟苯基)甲基]呋喃-2-基]乙酮 在 盐酸 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 1-(5-(4-氟苄基)呋喃-2-基)-3-羟基-3-(1H-1,2,4-三唑-3-基)-2-丙烯-1-酮
  参考文献：
  名称：

  Development of HIV-Integrase Inhibitor S-1360: Selection of the Protecting Group on the 1,2,4-Triazole Ring

  摘要：

  HIV-integrase inhibitor S-1360 was synthesized by Claisen-type reaction of 5-(4-fluorobenzyl)-2-furyl methyl ketone with N-protected 1H-1,2,4-triazole-3-carboxylate. The protecting group on the triazole ring is essential for the reaction to proceed. Tetrabydropyranyl and 1-methoxy-1-methylethyl groups were examined for manufacturing S-1360 on a large scale. High throughput and a convenient procedure were realized by using the 1-methoxy-1-methylethyl group.

  DOI：

  10.1021/op700116y
• 作为产物：
  描述：

  5-(4-fluorobenzyl)-furan-2-carboxylic acid 2-pyridylthioester 在 甲基溴化镁 作用下， 生成 1-[5-[(4-氟苯基)甲基]呋喃-2-基]乙酮
  参考文献：
  名称：

  EP1186599

  摘要：

  公开号：
• 作为试剂：
  描述：

  ethyl 1-(1-methoxy-1-methylethyl)-1H-1,2,4-triazole-3-carboxylate 、 1-[5-[(4-氟苯基)甲基]呋喃-2-基]乙酮 在 1-[5-[(4-氟苯基)甲基]呋喃-2-基]乙酮 作用下， 以83.6的产率得到1-[5-(4-fluorobenzyl)furan-2-yl]-3-hydroxy-3-[1-(1methoxy-1-methylethyl)-1H-1,2,4-triazole-3-yl]propenone
  参考文献：
  名称：

  Organic Process Research and Development. 2007, 11, 1055-1058

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Benzylation of Heterocyclic Aromatic Compounds
  作者：David Lapointe、Keith Fagnou

  DOI：10.1021/ol901689q

  日期：2009.9.17

  Broadly applicable palladium-catalyzed heteroarene benzylation reactions are described with a focus on the most challenging heterocyclic classes under traditional benzylation techniques such as sulfur-containing heterocycles and those bearing functional groups that would be incompatible with reactions requiring Lewis acids and/or strong bases.

  描述了广泛适用的钯催化的杂芳基苄基化反应，重点是传统苄基化技术下最具挑战性的杂环类，例如含硫杂环以及带有与需要路易斯酸和/或强碱的反应不相容的官能团的杂环。
• Medicinal compositions containing propenone derivatives
  申请人：——

  公开号：US20030171406A1

  公开（公告）日：2003-09-11

  A combination of an integrate inhibitor with an anti-retrovirus active substance and medical compositions containing the same as the active ingredients are found.

  一种将整合抑制剂与抗逆转录病毒活性物质组合使用的医药组合物被发现，该组合物以其作为活性成分。
• Heteroaromatic derivatives having an inhibitory activity against HIV integrase
  申请人：——

  公开号：US20040002485A1

  公开（公告）日：2004-01-01

  A compound of the formula (I): 1 wherein X is hydroxy, protected hydroxy or optionally substituted amino; Y is —COOR A wherein R A is hydrogen or ester residue, —CONR B R C wherein R B and R C each is independently hydrogen or amide residue, optionally substituted aryl or optionally substituted heteroaryl; and A 1 is optionally substituted heteroaryl; provided that a compound wherein Y and/or A 1 is optionally substituted indol-3-yl is excluded, a tautomer, a prodrug, a pharmaceutically acceptable salt or a hydrate thereof has an inhibitory activity against an integrase.

  式(I)的化合物：其中X为羟基，保护羟基或可选取代的氨基；Y为—COORA，其中RA为氢或酯基残基，—CONRBRC，其中RB和RC各自独立地为氢或酰胺基残基，可选取代的芳基或可选取代的杂芳基；且A1为可选取代的杂芳基；但其中Y和/或A1为可选取代的吲哚-3-基的化合物被排除，其互变异构体、前药、药物可接受的盐或水合物具有对整合酶的抑制活性。
• Inhibitor for enzyme having two divalent metal ions as active centers
  申请人：——

  公开号：US20040039060A1

  公开（公告）日：2004-02-26

  A pharmaceutical composition for use as an inhibitor of an enzyme having two divalent metal ions as an active center was found. It is possible to inhibit the activity of an enzyme by a compound capable of chelating both of the two divalent metal ions.

  发现了一种用作酶抑制剂的药物组合物，该酶具有两个二价金属离子作为活性中心。能够通过一种化合物来螯合这两个二价金属离子，从而抑制酶活性。
• Processes for the preparation of substituted propenone derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US06831177B1

  公开（公告）日：2004-12-14

  Industrial and commercial processes for the preparation of 2-acyl-5-benzylfuran derivatives, 1,2,4-triazole-3-carboxylic acid ester derivatives or propenone derivatives having an anti-HIV activity; and useful crystals of the derivatives. A deblocking: (III-2), (IV-10), (VI-1), wherein R1, R2 and R4 are each independently hydrogen or the like; A is CR6 or N; R6 is hydrogen or the like; Q is a protecting group; and L is a leaving group.

  制备具有抗HIV活性的2-酰基-5-苄基呋喃衍生物、1,2,4-三唑-3-羧酸酯衍生物或丙烯酮衍生物的工业和商业过程；以及这些衍生物的有用晶体。解保护反应: (III-2), (IV-10), (VI-1)，其中R1、R2和R4各自独立地为氢或类似物；A为CR6或N；R6为氢或类似物；Q为保护基；L为离去基团。