ethyl 2-(4-pyrrolidinophenylmethyl)acetoacetate | 452963-76-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 2-(4-pyrrolidinophenylmethyl)acetoacetate
• 英文别名: Ethyl 3-oxo-2-[(4-pyrrolidin-1-ylphenyl)methyl]butanoate
• CAS: 452963-76-7
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: ACCONZZCYHLVPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-pyrrolidinophenylmethyl)acetoacetate 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以63%的产率得到4-(4-pyrrolidinophenylmethyl)-3-methyl-5(4H)-isoxazolone
  参考文献：
  名称：

  Novel Non-Steroidal/Non-Anilide Type Androgen Antagonists with an Isoxazolone Moiety

  摘要：

  3-Substitutcd (Z)-4-(4-N,N-dialkylaminophenylmethylene)-5(4H)-isoxazolones and related compounds were designed and prepared as candidates for structurally novel androgen antagonists. Several compounds showed potent anti-androgenic activity as assessed by nuclear androgen receptor binding assay and growth inhibition assay using androgen-dependent Shionogi carcinoma cells SC-3. They were approximately 10-220 times more potent than flutamide in these assay systems, They also showed anti-androgenic activity toward prostate tumor cell line LNCaP, which has an aberrant nuclear androgen receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00421-7
• 作为产物：
  描述：

  1-苯基吡咯烷 、 聚合甲醛 、 乙酰乙酸乙酯 以 溶剂黄146 为溶剂， 以11%的产率得到ethyl 2-(4-pyrrolidinophenylmethyl)acetoacetate
  参考文献：
  名称：

  Novel Non-Steroidal/Non-Anilide Type Androgen Antagonists with an Isoxazolone Moiety

  摘要：

  3-Substitutcd (Z)-4-(4-N,N-dialkylaminophenylmethylene)-5(4H)-isoxazolones and related compounds were designed and prepared as candidates for structurally novel androgen antagonists. Several compounds showed potent anti-androgenic activity as assessed by nuclear androgen receptor binding assay and growth inhibition assay using androgen-dependent Shionogi carcinoma cells SC-3. They were approximately 10-220 times more potent than flutamide in these assay systems, They also showed anti-androgenic activity toward prostate tumor cell line LNCaP, which has an aberrant nuclear androgen receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00421-7

文献信息

• Novel Mannich-type nucleophilic substitution reaction with tertiary aromatic amines
  作者：Hiroyasu Takahashi、Nobuyuki Kashiwa、Yuichi Hashimoto、Kazuo Nagasawa

  DOI：10.1016/s0040-4039(02)00447-1

  日期：2002.4

  A novel formaldehyde-mediated condensation reaction of N,N-dialkyl aromatic amines and resonance-stabilized carbon nucleophiles is described. A condensation reaction between N,N-dimethylaniline (4) and ethyl acetoacetate (8) in the presence of formaldehyde in acetic acid took place to give 2-(4-dimethylaminobenzyl)-3-oxo butyric acid ethyl ester (9) together with the dimerization product 7 in 73 and

  描述了N，N-二烷基芳族胺与共振稳定的碳亲核试剂的新的甲醛介导的缩合反应。N，N-二甲基苯胺（4）与乙酰乙酸乙酯（8）在甲醛存在下于乙酸中发生缩合反应，得到2-（4-二甲基氨基苄基）-3-氧代丁酸乙酯（9）和二聚产物7的产率分别为73％和21％。该缩合反应进一步用于合成4-取代的二烷基苯胺衍生物。