3-phenyl-1-propyl 1-imidazolecarboxylate | 170895-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-phenyl-1-propyl 1-imidazolecarboxylate
• 英文别名: 1-(3-phenylpropoxycarbonyl)-1H-imidazole；3-Phenylpropyl imidazole-1-carboxylate
• CAS: 170895-01-9
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: BEWGSLMPENEQHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  385.8±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-propyl 1-imidazolecarboxylate 在 1-环己烯氧基三甲基硅烷 、 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以48%的产率得到bis(3-phenylpropyl) carbonate
  参考文献：
  名称：

  Synthesis of Enol Carbonates from a Reaction of Silyl Enolates with 1H-Imidazolylurethane

  摘要：

  Enol Carbonates (6) were prepared by treatment of trimethylsilyl enolates (5) with 1-alkoxycarbonyl-1H-imidazoles (2) in the presence of boron trifluoride etherate and tetrabutylammonium fluoride.

  DOI：

  10.3987/com-95-7048
• 作为产物：
  描述：

  3-苯丙醇 、 N,N'-羰基二咪唑 在 吡啶溴化氢盐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-phenyl-1-propyl 1-imidazolecarboxylate
  参考文献：
  名称：

  布朗斯台德酸诱导的脂肪族氨基咪唑氨基甲酸酯被卤离子亲核取代的机理研究

  摘要：

  在本文中，我们报道了在布朗斯台德酸性条件下，氨基甲酸咪唑对卤离子进行亲核取代的有趣反应性。取决于反应条件，卤离子可以容易地攻击羧基位置并触发脱羧烷基卤的形成。或者，还发现卤离子竞争性地经历亲核酰基取代，最终导致生成碳酸盐二聚产物。

  DOI：

  10.1016/j.tetlet.2015.01.098

文献信息

• Simple Method for the Preparation of Esters from Grignard Reagents and Alkyl 1-Imidazolecarboxylates
  作者：Thomas Werner、Anthony G. M. Barrett

  DOI：10.1021/jo060562m

  日期：2006.5.1

  The reaction of Grignard reagents with alkyl imidazolecarboxylates, which were prepared from alcohols with carbonyl diimidazole, gave the corresponding esters in good to excellent yields. This method conveniently provides esters from alkyl halides and alcohols by C1-carbon chain extension.

  由醇与羰基二咪唑制备的格利雅试剂与烷基咪唑羧酸酯的反应以良好或优异的收率得到了相应的酯。该方法方便地通过C 1-碳链增长从烷基卤化物和醇提供酯。
• [EN] PROCESS FOR PREPARATION OF SOLRIAMFETOL AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE SOLRIAMFÉTOL ET SES INTERMÉDIAIRES
  申请人：LUPIN LTD

  公开号：WO2021161232A1

  公开（公告）日：2021-08-19

  The present invention relates to a process for the preparation of dopamine and norepinephrine reuptake inhibitor (DNRI) compound Solriamfetol and pharmaceutically acceptable salts thereof, having the chemical name (R)-2-amino- 3-phenylpropyl carbamate (APC) by using novel intermediates. (I)

  本发明涉及一种制备多巴胺和去甲肾上腺素再摄取抑制剂（DNRI）化合物Solriamfetol及其药用可接受盐的方法，其化学名称为（R）-2-氨基-3-苯基丙基氨甲酸酯（APC），通过使用新颖的中间体。（I）
• Synthesis, molecular modeling and biological evaluation of aza-proline and aza-pipecolic derivatives as FKBP12 ligands and their in vivo neuroprotective effects
  作者：Douglas E Wilkinson、Bert E Thomas、David C Limburg、Agnes Holmes、Hansjorg Sauer、Douglas T Ross、Raj Soni、Yi Chen、Hong Guo、Pamela Howorth、Heather Valentine、Dawn Spicer、Mike Fuller、Joseph P Steiner、Gregory S Hamilton、Yong-Qian Wu

  DOI：10.1016/s0968-0896(03)00478-4

  日期：2003.11

  Nonimmunosuppressant ligands, exemplified by GPI 1046 (1), for the peptidyl-prolyl isomerase FKBP12 have been found to unexpectedly possess powerful neuroprotective and neuroregenerative effects in vitro and in vivo. We have extensively explored the therapeutic utility of FKBP12 ligands based on analogues of proline and pipecolic acid. As part of our ongoing program to explore novel structural classes of FKBP12 ligands, we herein wish to report a new class of FKBP12 ligands containing aza-proline and aza-pipecolic acid analogues. Details of the synthetic studies, together with biological activity will be presented. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of Enol Carbonates from a Reaction of Silyl Enolates with 1H-Imidazolylurethane
  作者：Shunsaku Ohta、Masayuki Yamashita、Nobuaki Nagai、Ikuo Kawasaki、Kazuto Maeda、Yoshiko Miyano

  DOI：10.3987/com-95-7048

  日期：——

  Enol Carbonates (6) were prepared by treatment of trimethylsilyl enolates (5) with 1-alkoxycarbonyl-1H-imidazoles (2) in the presence of boron trifluoride etherate and tetrabutylammonium fluoride.
• Mechanistic insights into Brønsted acid-induced nucleophilic substitution of aliphatic imidazole carbamate with halide ions
  作者：Mirza A. Saputra、Rashel L. Forgey、Jeffrey L. Henry、Rendy Kartika

  DOI：10.1016/j.tetlet.2015.01.098

  日期：2015.3

  interesting reactivity of imidazole carbamate towards nucleophilic substitution with halide ions under Brønsted acidic conditions. Depending upon reaction conditions, halide ions could readily attack the carboxyl position and trigger decarboxylative alkyl halide formation. Alternatively, halide ions were also found to competitively undergo nucleophilic acyl substitution, which ultimately results in the

  在本文中，我们报道了在布朗斯台德酸性条件下，氨基甲酸咪唑对卤离子进行亲核取代的有趣反应性。取决于反应条件，卤离子可以容易地攻击羧基位置并触发脱羧烷基卤的形成。或者，还发现卤离子竞争性地经历亲核酰基取代，最终导致生成碳酸盐二聚产物。