Tert-butyl 4-[3-(dicyanomethyl)-4,4-dimethoxybutyl]benzoate | 134373-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Tert-butyl 4-[3-(dicyanomethyl)-4,4-dimethoxybutyl]benzoate
• CAS: 134373-01-6
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: MPNNYWMBRDWRNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-[3-(dicyanomethyl)-4,4-dimethoxybutyl]benzoate 在 potassium tert-butylate 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 4-<2-(2,4-Diaminopyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoic acid
  参考文献：
  名称：

  A novel synthetic approach to pyrrolo[2,3-d]pyrimidine antifolates

  摘要：

  A novel and efficient synthetic method for the synthesis of pyrrolo[2,3-d]pyrimidine antifolates is described. The key reaction of this method is the photo-initiated free radical addition of bromomalononitrile or ethyl bromocyanoacetate to an enol ether to afford the backbone skeleton of the targeted antifolate molecule. The key intermediates 3 or 4 are smoothly converted to the pyrrolo[2,3-d]pyrimidine antifolates 1 or 2 in three steps and in high overall yield.

  DOI：

  10.1021/jo00059a016
• 作为产物：
  描述：

  3-(4-[2,2-二甲基乙基]羧基苯基)-1-丙醛 在 potassium tert-butylate 作用下， 反应 2.67h， 生成 Tert-butyl 4-[3-(dicyanomethyl)-4,4-dimethoxybutyl]benzoate
  参考文献：
  名称：

  A novel synthetic approach to pyrrolo[2,3-d]pyrimidine antifolates

  摘要：

  A novel and efficient synthetic method for the synthesis of pyrrolo[2,3-d]pyrimidine antifolates is described. The key reaction of this method is the photo-initiated free radical addition of bromomalononitrile or ethyl bromocyanoacetate to an enol ether to afford the backbone skeleton of the targeted antifolate molecule. The key intermediates 3 or 4 are smoothly converted to the pyrrolo[2,3-d]pyrimidine antifolates 1 or 2 in three steps and in high overall yield.

  DOI：

  10.1021/jo00059a016

文献信息

• Production of pyrrolopyrimidines and intermediates therefor
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0402903A1

  公开（公告）日：1990-12-19

  There is provided an improved process for producing novel compounds represented by the general formula: wherein the ring Ⓐ a pyrrole ring which may be hydrogenated; X represents an amino, hydroxyl or mercapto group R¹, R² and R³ each, being the same as or different from the other, represents hydrogen or an alkyl, alkenyl or alkynyl group which may be substituted: R⁴ represents OR⁵ wherein R⁵ represents hydrogen or a hydrocarbon group which may be substituted or NHCH(COOR⁶)CH₂CH₂COOR⁷ wherein R⁶ and R⁷ each represents hydrogen or a hydrocarbon group which may be substituted; and n represents an integer of 1 to 4, or a salt thereof from compounds represented by the general formula: wherein X, R¹, R², R³, R⁴ and n are the same as defined above; Y¹ and Y² each represents oxygen or sulfur atom; R⁸ and R⁹ each, being the same as or different from the other, represents a hydrocarbon group which may be substituted, or salts thereof by an intramolecular ring closure reaction ot form a pyrrolo­pyrimidine ring and, if necessary, reducing pyrrole ring thus formed to pyrroline ring. The compound are useful as antitumor agents.

  本发明提供了一种生产通式所代表的新型化合物的改进工艺： 其中环Ⓐ为可氢化的吡咯环；X代表氨基、羟基或巯基 R¹、R²和R³各自相同或不同地代表氢或可被取代的烷基、烯基或炔基：R⁴ 代表 OR⁵，其中 R⁵ 代表氢或可被取代的烃基或 NHCH(COOR⁶)CH₂CH₂COOR⁷，其中 R⁶ 和 R⁷ 各自代表氢或可被取代的烃基；以及 n 代表 1 至 4 的整数，或通式所代表化合物的盐： 其中，X、R¹、R²、R³、R⁴ 和 n 与上述定义相同；Y¹ 和 Y² 各自代表氧原子或硫原子；R⁸ 和 R𠞙 各自代表可被取代的烃基，或其盐通过分子内封环反应形成吡咯并嘧啶环，必要时将由此形成的吡咯环还原为吡咯啉环。这些化合物可用作抗肿瘤药物。
• US5349064A
  申请人：——

  公开号：US5349064A

  公开（公告）日：1994-09-20
• US5496946A
  申请人：——

  公开号：US5496946A

  公开（公告）日：1996-03-05
• A novel synthetic approach to pyrrolo[2,3-d]pyrimidine antifolates
  作者：Tetsuo Miwa、Takenori Hitaka、Hiroshi Akimoto

  DOI：10.1021/jo00059a016

  日期：1993.3

  A novel and efficient synthetic method for the synthesis of pyrrolo[2,3-d]pyrimidine antifolates is described. The key reaction of this method is the photo-initiated free radical addition of bromomalononitrile or ethyl bromocyanoacetate to an enol ether to afford the backbone skeleton of the targeted antifolate molecule. The key intermediates 3 or 4 are smoothly converted to the pyrrolo[2,3-d]pyrimidine antifolates 1 or 2 in three steps and in high overall yield.