ethyl 4-(ethylenediamine)benzoate | 86234-55-1

• 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: ethyl 4-(ethylenediamine)benzoate
• 英文别名: Ethyl 4[N-(2-aminoethyl)]aminobenzoate；Ethyl 4-(2-aminoethylamino)benzoate
• CAS: 86234-55-1
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: NBNWNYNSPNCQAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-丙-1-烯-2-基苯甲酸 、 ethyl 4-(ethylenediamine)benzoate 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 对苯醌 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成
  参考文献：
  名称：

  亲核分子链烷烃的钯催化串联羰基化氮杂-瓦克型环化反应，以获取熔融的N-杂环

  摘要：

  尽管串联反应可在一锅反应中快速接近结构复杂的分子，但选择性问题仍需解决，特别是涉及不相容的阶跃反应时。在此，我们报道了通过亲核连接的链烯基酰胺和一氧化碳通过以下方法选择性合成稠合的N-杂环钯（Pd）催化的串联羰基化氮杂-瓦克型环化反应。酰胺NH的电子不足性质以及Pd与烯烃的分子内配位会加速氨基palpalation，并有效防止二胺部分的侧氧化羰基化形成尿素。还发现报道的酰基Pd氯化物中间体可能不参与该串联环化。这项工作不仅为融合1，4-二氮杂潘酮和1,4-二氮杂潘酮提供了有效的合成途径，而且还激发了串联反应的进一步发展，以实现杂环的多样化合成。

  DOI：

  10.1002/cjoc.202000491
• 作为产物：
  描述：

  2-唑烷酮 、 苯佐卡因盐酸盐 以 various solvent(s) 为溶剂， 以61%的产率得到ethyl 4-(ethylenediamine)benzoate
  参考文献：
  名称：

  The use of 2-oxazolidinones as latent aziridine equivalents. 2. Aminoethylation of aromatic amines, phenols, and thiophenols

  摘要：

  The utility of 2-oxazolidinones 1 as latent, carboxylated aziridine functionalities was examined. Reaction of 2-oxazolidinone (1a), 3-methyl-2-oxazolidinone (1b), 3-(phenylmethyl)-2-oxazolidinone (1c), 3-phenyl-2-oxazolidinone (1d), 4,4-dimethyl-2-oxazolidinone (1e), and 5-ethyl-2-oxazolidinone (1f) with aromatic amine salts, phenol, or thiophenols at elevated temperatures (> 130-degrees-C) afforded aminoethylated adducts. The aminoethylation occurred with concomitant loss of carbon dioxide to furnish variously substituted N-aryl-1,2-ethanediamines 4, 1-(2-phenoxyethyl)-2-imidazolidinone (8), or 2-(arylthio)ethanamines 9 on reactions of 1 with aromatic amine salts, phenol, and thiophenols, respectively. Imidazolidinone 8 is believed to be a secondary reaction product resulting from the condensation of the initially formed 2-phenoxyethanamine with starting oxazolidinone 1a. The aminoethylation reaction did not proceed with aliphatic amine hydrochlorides or alkyl mercaptans. Preliminary mechanistic pathways for these ring openings were also investigated employing a specific, C-5 deuterium-labeled oxazolidinone 1b-d2. Ring-opening experiments of 1b-d2 with N-methylaniline hydrochloride suggest reaction can occur through either a dioxazolinium 5 and/or an aziridinium 6 intermediate. In contrast, reaction of 1b-d2 with thiophenol suggests ring-opening to proceed only via the dioxazolinium pathway.

  DOI：

  10.1021/jo00049a037

文献信息

• [EN] C-28 AMIDES OF MODIFIED C-3 BETULINIC ACID DERIVATIVES AS HIV MATURATION INHIBITORS<br/>[FR] AMIDES C-28 DE DÉRIVÉS D'ACIDE BÉTULINIQUE MODIFIÉS EN C-3, UTILISÉS COMME INHIBITEURS DE MATURATION DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011153319A1

  公开（公告）日：2011-12-08

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, modified C-3 and C-28 betulinic acid derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors. These compounds are useful for the treatment of HIV and AIDS.

  具有药物和生物活性的化合物、其药物组合物及其使用方法。特别是，提供了一种具有独特抗病毒活性的改性C-3和C-28桦木酸衍生物，用作HIV成熟抑制剂。这些化合物可用于治疗HIV和艾滋病。
• Development of an S_NAr Reaction: A Practical and Scalable Strategy To Sequester and Remove HF
  作者：A. John Blacker、Gabriel Moran-Malagon、Lyn Powell、William Reynolds、Rebecca Stones、Michael R. Chapman

  DOI：10.1021/acs.oprd.8b00090

  日期：2018.9.21

  simple and operationally practical method to sequester and remove fluoride generated through the SNAr reaction between amines and aryl fluorides is reported. Calcium propionate acts as an inexpensive and environmentally benign in situ scrubber of the hydrofluoric acid byproduct, which is simply precipitated and filtered from the reaction mixture during standard aqueous workup. The method has been tested

  报道了一种简单且操作上可行的方法，用于隔离和去除通过胺与芳基氟化物之间的S N Ar反应生成的氟化物。丙酸钙可作为氢氟酸副产物的廉价且对环境无害的原地洗涤器，在标准的水后处理过程中，氢氟酸副产物可以简单地从反应混合物中沉淀出来并过滤掉。该方法已在10到100 g的操作规模上进行了测试，显示在每种情况下氟化物含量均降低> 99.5％。两种规模的氟化钙都得到了全面的回收，这证明这是一种通用，有效且健壮的氟化物提取方法，有助于防止搪玻璃反应堆腐蚀。
• Aminoethylation process
  申请人：The Dow Chemical Company

  公开号：US04381401A1

  公开（公告）日：1983-04-26

  2-Oxazolidinone or N-substituted derivatives thereof are reacted with aromatic amine hydrochlorides at elevated temperatures to produce 1,2-ethanediamines.

  2-噁唑啉酮或其N-取代衍生物在高温下与芳香胺盐酸盐反应，生成1,2-乙二胺。
• C-28 AMIDES OF MODIFIED C-3 BETULINIC ACID DERIVATIVES AS HIV MATURATION INHIBITORS
  申请人：Regueiro-Ren Alicia

  公开号：US20120142653A1

  公开（公告）日：2012-06-07

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, modified C-3 and C-28 betulinic acid derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors. These compounds are useful for the treatment of HIV and AIDS.

  本发明涉及具有药物和生物影响性质的化合物、它们的制药组合物和使用方法。具体而言，提供了具有独特的抗病毒活性的改性C-3和C-28桦酸衍生物作为HIV成熟抑制剂。这些化合物对于治疗HIV和艾滋病非常有用。
• Cinnamamide derivatives
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0407200A1

  公开（公告）日：1991-01-09

  Novel cinnamamide derivatives and the salts thereof are provided. An antihyperlipidemic composition is also provided. The composition comprises an active ingredient which is at least one selected from the group consisting of the above-mentioned cinnamamide derivative and the pharmaceutically acceptable salt thereof.

  本研究提供了新型肉桂酰胺衍生物及其盐类。还提供了一种抗高血脂组合物。该组合物包含至少一种选自上述肉桂酰胺衍生物及其药学上可接受的盐所组成的组的活性成分。