tert-butyl 4-(5-methoxy-4-pentenyl)benzoate | 134373-02-7

• 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-(5-methoxy-4-pentenyl)benzoate
• 英文别名: tert-butyl 4-(5-methoxypent-4-enyl)benzoate
• CAS: 134373-02-7
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: FADXNJDAQBEVKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(5-methoxy-4-pentenyl)benzoate 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 4.17h， 生成 tert-butyl 4-<4-(2,4,6-triaminopyrimidin-5-yl)-5,5-dimethoxypentyl>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
• 作为产物：
  描述：

  tert-butyl 4-(4-hydroxy-1-butenyl)benzoate 在 palladium on activated charcoal 草酰氯 、 potassium tert-butylate 、 氢气 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 tert-butyl 4-(5-methoxy-4-pentenyl)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：US05496946A1

  公开（公告）日：1996-03-05

  There is provided an improved process for producing novel compounds represented by the general formula: ##STR1## wherein the ring A/ represents a pyrrole ring which may be hydrogenated; X represents an amino, hydroxyl or mercapto group; R.sup.1, R.sup.2 and R.sup.3 each, being the same as or different from the other, represents hydrogen or an alkyl, alkenyl or alkynyl group which may be substituted; R.sup.4 represents OR.sup.5 wherein R.sup.5 represents hydrogen or a hydrocarbon group which may be substituted or NHCH(COOR.sup.6)CH.sub.2 CH.sub.2 COOR.sup.7 wherein R.sup.6 and R.sup.7 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: ##STR2## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are the same as defined above; Y.sup.1 and Y.sup.2 each represents oxygen or sulfur atom; R.sup.8 and R.sup.9 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 to form a pyrrolopyrimidine ring and, if necessary, reducing pyrrole ring thus formed to pyrroline ring. The compounds are useful as antitumor agents.

  提供了一种改进的制备新化合物的方法，该化合物通式表示为：##STR1## 其中环A /表示可能氢化的吡咯环; X表示氨基，羟基或巯基; R.sup.1，R.sup.2和R.sup.3分别与另一个相同或不同，表示氢或可取代的烷基，烯基或炔基; R.sup.4表示OR.sup.5，其中R.sup.5表示氢或可取代的碳氢基或NHCH（COOR.sup.6）CH.sub.2 CH.sub.2 COOR.sup.7，其中R.sup.6和R.sup.7各自表示氢或可取代的碳氢基; n表示1到4的整数，或其盐，来自通式表示的化合物：##STR2## 其中X，R.sup.1，R.sup.2，R.sup.3，R.sup.4和n与上述定义相同; Y.sup.1和Y.sup.2各表示氧或硫原子; R.sup.8和R.sup.9各自与另一个相同或不同，表示可取代的碳氢基，或其盐，通过分子内环闭合反应形成吡咯嘧啶环，并如有必要，还原形成的吡咯环至吡咯烃环。这些化合物可用作抗肿瘤剂。
• 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.