2-phenylethyl carbonylimidazolide | 170895-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenylethyl carbonylimidazolide
• 英文别名: 2-Phenylethyl imidazole-1-carboxylate
• CAS: 170895-03-1
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: SCWXHPMRUNVMPK-UHFFFAOYSA-N

物化性质

• 沸点：
  370.8±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2-phenylethyl carbonylimidazolide 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-phenylethyl 2-(3,3-dimethyl-2-oxopentanoyl)-pyrazolidinecarboxylate
  参考文献：
  名称：

  Synthesis, molecular modeling and biological evaluation of aza-proline and aza-pipecolic derivatives as FKBP12 ligands and their in vivo neuroprotective effects

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(03)00478-4
• 作为产物：
  描述：

  苯乙醇 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 生成 2-phenylethyl carbonylimidazolide
  参考文献：
  名称：

  氨基甲酸酯挤出烷基化合成叔胺

  摘要：

  碱性胺是许多具有生物活性的天然产物和药物的关键元素。鉴于其固有的反应性，在靶向合成过程中通常需要保护碱性胺，这会导致保护/脱保护序列的浪费。我们报告了一种分步经济的方法，能够在仲胺通过 CO 2的正式挤出转化为叔胺之前将其保护为氨基甲酸酯。该方法适用于 iboga 生物碱 (±)-conodusine A 和 (±)-conodusine B 的合成。

  DOI：

  10.1021/acs.orglett.2c02516

文献信息

• Design and comparative anticonvulsant activity assessment of CNS-active alkyl-carbamoyl imidazole derivatives
  作者：Hafiz Mawasi、David Bibi、Meir Bialer

  DOI：10.1016/j.bmc.2016.07.018

  日期：2016.9

  A novel series of carbamoyl derivatives of alkylimidazole has been designed and their anticonvulsant activity was comparatively evaluated in the mice- and rats-maximal-electroshock (MES), subcutaneous-metrazol (scMet) seizure tests and the mice-6Hz psychomotor (6Hz) models. The ten new designed molecules contain in their chemical structure imidazole, alkyl side-chain and carbamate as three potential

  设计了一系列新型的烷基咪唑氨基甲酰基衍生物，并在小鼠和大鼠最大电击（MES），皮下metrazol（scMet）癫痫发作试验和小鼠6Hz精神运动（6Hz）模型中比较了它们的抗惊厥活性。 。十个新设计的分子在其化学结构中包含咪唑，烷基侧链和氨基甲酸酯作为三个潜在的活性部分。尽管氨基甲酰基咪唑衍生物具有紧密的结构特征，但在MES试验中只有化合物7、8、13和16才具有活性，ED50值在12至20mg / kg的范围内，并具有较高的保护指数（PI = TD50 / ED50）。给大鼠腹膜内注射后的4.1-7.3。在化合物7、8、9、12的MES-ED50值为14-26mg / kg的小鼠中观察到了类似的现象。化合物7和13在6Hz模型中也表现出抗惊厥活性，ED50值分别为32和44mg / kg。作为活性最高的化合物，化合物7、8以及随后的13和16提供了最佳的疗效安全性，因此可能有望成为开发新型抗癫痫药的候选药物。
• Synthetic process for trans-aminocyclohexyl ether compounds
  申请人：Barrett G. M. Anthony

  公开号：US20050038256A1

  公开（公告）日：2005-02-17

  A method of stereoselectively making an aminocyclohexyl ether comprises, for example, reacting to form the aminocyclohexyl ether having the formula respectively, wherein independently at each occurrence, R 1 and R 2 are independently hydrogen, C 1 -C 8 alkyl, C 3 -C 8 alkoxyalkyl, C 1 -C 8 hydroxyalkyl, or C 7 -C 12 aralkyl; or R 1 and R 2 are independently C 3 -C 8 alkoxyalkyl, C 1 -C 8 hydroxyalkyl, and C 7 -C 12 aralkyl; or R 1 and R 2 , when taken together with the nitrogen atom to which they are directly attached in formula (57) or (75), form a ring denoted by formula (I): wherein the ring of formula (I) is formed from the nitrogen as shown as well as three to nine additional ring atoms independently carbon, nitrogen, oxygen, or sulfur; where any two adjacent ring atoms may be joined together by single or double bonds, and where any one or more of the additional carbon ring atoms may be substituted with one or two substituents selected from the group consisting of hydrogen, hydroxy, C 1 -C 3 hydroxyalkyl, oxo, C 2 -C 4 acyl, C 1 -C 3 alkyl, C 2 -C 4 alkylcarboxy, C 1 -C 3 alkoxy, and C 1 -C 20 alkanoyloxy, or may be substituted to form a spiro five- or six-membered heterocyclic ring containing one or two oxygen and/or sulfur heteroatoms; or any two adjacent additional carbon ring atoms may be fused to a C 3 -C 8 carbocyclic ring, and any one or more of the additional nitrogen ring atoms may be substituted with substituents selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 4 acyl, C 2 -C 4 hydroxyalkyl and C 3 -C 8 alkoxyalkyl; or R 1 and R 2 , when taken together with the nitrogen atom to which they are directly attached in formula (I), may form a bicyclic ring system selected from the group consisting of 3-azabicyclo[3.2.2]nonan-3-yl, 2-azabicyclo[2.2.2]octan-2-yl, 3-azabicyclo[3.1.0]hexan-3-yl, and 3-azabicyclo[3.2.0]heptan-3-yl; and wherein R 3 , R 4 and R 5 are independently bromine, chlorine, fluorine, carboxy, hydrogen, hydroxy, hydroxymethyl, methanesulfonamido, nitro, cyano, sulfamyl, trifluoromethyl, C 2 -C 7 alkanoyloxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 7 alkoxycarbonyl, C 1 -C 6 thioalkyl, aryl or N(R 6 ,R 7 ) where R 6 and R 7 are independently hydrogen, acetyl, methanesulfonyl or C 1 -C 6 alkyl; or R 3 , R 4 and R 5 are independently hydrogen, hydroxy or C 1 -C 6 alkoxy; with the proviso that R 3 , R 4 and R 5 cannot all be hydrogen; and wherein O-J is a leaving group. Methods of making intermediates are also disclosed.

  一种立体选择性制备氨基环己醚的方法，例如，反应生成具有以下式子的氨基环己醚，其中在每个出现的位置上，独立的R1和R2分别为氢、C1-C8烷基、C3-C8烷氧基烷基、C1-C8羟基烷基或C7-C12芳基烷基；或者独立的R1和R2为C3-C8烷氧基烷基、C1-C8羟基烷基和C7-C12芳基烷基；或者R1和R2与它们直接连接的氮原子一起形成由以下式子表示的环：其中式子（I）的环由氮原子形成，以及三到九个独立的环原子，包括碳、氮、氧或硫；任意相邻的两个环原子可以通过单键或双键连接在一起，任何一个或多个额外的碳环原子可以被氢、羟基、C1-C3羟基烷基、氧代、C2-C4酰基、C1-C3烷基、C2-C4烷基羧基、C1-C3烷氧基或C1-C20烷酰氧基中的一个或两个取代，或者被取代以形成一个螺五元或六元杂环环，其中包含一个或两个氧和/或硫杂原子；任意相邻的两个额外碳环原子可以融合到一个C3-C8碳环中，任何一个或多个额外的氮环原子可以被氢、C1-C6烷基、C2-C4酰基、C2-C4羟基烷基和C3-C8烷氧基烷基中的一个或多个取代；或者R1和R2与它们直接连接的氮原子一起形成从以下组中选择的双环系统：3-氮杂双环[3.2.2]壬烷-3-基、2-氮杂双环[2.2.2]辛烷-2-基、3-氮杂双环[3.1.0]己烷-3-基和3-氮杂双环[3.2.0]庚烷-3-基；其中R3、R4和R5独立地为溴、氯、氟、羧基、氢、羟基、羟甲基、甲磺酰胺基、硝基、氰基、磺酰胺基、三氟甲基、C2-C7烷酰氧基、C1-C6烷基、C1-C6烷氧基、C2-C7烷氧羰基、C1-C6硫代烷基、芳基或N（R6，R7），其中R6和R7独立地为氢、乙酰、甲磺酰或C1-C6烷基；或者R3、R4和R5独立地为氢、羟基或C1-C6烷氧基；但是R3、R4和R5不能都为氢；O-J是一个离去基团。还公开了制备中间体的方法。
• Photoreleasable protecting groups based on electron transfer chemistry. Donor sensitized release of phenacyl groups from alcohols, phosphates and diacids
  作者：Anamitro Banerjee、Kwangjoo Lee、Daniel E. Falvey

  DOI：10.1016/s0040-4020(99)00754-1

  日期：1999.10

  The electron transfer mediated photochemical release of alcohols, phosphates and diacids is examined. The alcohols can be protected as mixed phenacyl carbonate esters. Irradiation of mixtures containing electron donating sensitizers and phenacyl alkyl carbonate ester initiates a series of bond scission reactions that result in clean release of the corresponding alcohols. This was demonstrated for a variety of primary, secondary and tertiary hydroxyl groups, including the 5'-hydroxy group of thymidine. Sensitizers that were effective in promoting photolytic release include 9,10-dimethylanthracene and 9-methylcarbazole. GC/MS and NMR analysis of the by-products formed in these release reactions implicates the intermediacy of radical ion intermediates in these reactions. It is further demonstrated that the electron transfer sensitized release method can be extended to phosphate esters and di-functional acids. (C) 1999 Elsevier Science 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.
• A New Simple One-Pot Regioselective Preparation of Mixed Diesters of Carbonic Acid
  作者：Giorgio Bertolini、Gianfranco Pavich、Barbara Vergani

  DOI：10.1021/jo980286e

  日期：1998.8.1