1-phthalimidyl-2-butene | 66784-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1-phthalimidyl-2-butene
• 英文别名: 2-(but-2-enyl)isoindoline-1,3-dione；N-((E/Z)-but-2-enyl)phthalimide；2-But-2-enylisoindole-1,3-dione
• CAS: 66784-19-8
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: PMUYLAJCELXRCO-UHFFFAOYSA-N

物化性质

• 熔点：
  77.5-79.5 °C
• 沸点：
  314.5±21.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phthalimidyl-2-butene 在 一水合肼 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以98%的产率得到crotylamine hydrochloride
  参考文献：
  名称：

  N-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligands

  摘要：

  Previous studies have shown that several imidazole derivatives posses affinity to histamine H-3 and H-4 receptors. Continuing our study on structural requirements responsible for affinity and selectivity for H-3/H-4 receptor subtypes, two series of 3-(1H-imidazol-4-yl) propyl carbamates were prepared: a series of unsaturated alkyl derivatives (1-9) and a series possessing a cycloalkyl group different distances to the carbamate moiety (10-13). The compounds were tested for their affinities at the human histamine H3 receptor, stably expressed in CHO-K1 cells. Compounds 1, 2, 5-7, 10-13 were investigated for their affinities at the human histamine H-4 receptor co-expressed with G alpha(i2) and G beta(1)gamma(2) subunits in Sf9 cells. To expand the pharmacological profile, compounds were further tested for their H3 receptor antagonist activity on guinea pig ileum and in vivo after oral administration to mice. All tested compounds exhibited good affinity for the human histamine H-3 receptor with K-i values in the range from 14 to 194 nM. All compounds were active in vivo after peroral administration (p.o.) to Swiss mice, thus demonstrating their ability to cross the blood-brain barrier. The most potent H-3 receptor ligand of these series was compound 5, 3-(1H-imidazol-4-yl) propyl pent-4-enylcarbamate with the highest affinity (K-i = 14 nM). Additionally, compound 3 showed remarkable central nervous system (CNS) H3R activity, increasing the N-tau-methylhistamine levels in mice with an ED50 value of 0.55 mg/kg, p.o. evidencing therefore, a twofold increase of inverse agonist/antagonist potency compared to the reference inverse agonist/antagonist thioperamide. In this study, the imidazole propyloxy carbamate moiety was kept constant. The different lipophilic moieties connected to the carbamate functionality in the eastern part of the molecule had a range of influences on the human H-4 receptor affinity (154-1326 nM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.046
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 1-溴-2-丁烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-phthalimidyl-2-butene
  参考文献：
  名称：

  Palladium-catalyzed allylic C–H amination of alkenes with N-fluorodibenzenesulfonimide: water plays an important role

  摘要：

  开发了一种新的基于钯催化的高区域选择性烯烃的烯丙基C–H氨化反应，使用NFSI并在催化量水的存在下进行。同时成功扩展到了在室温下使用Selectfluor介导的钯催化烯烃与N-托烯基氨基酸的氨化反应。

  DOI：

  10.1039/c2cc16720d

文献信息

• Asymmetric allylic substitution by chiral palladium catalysts: Which is more reactive, major π-allyl Pd(II) species or minor π-allyl species?
  作者：Chisato Urano、Masatoshi Onuki、Yuuta Uchida、Risa Suzuki、Kiyoshi Sato、Dai Masui、Motowo Yamaguchi、Takamichi Yamagishi

  DOI：10.1016/j.mcat.2020.111221

  日期：2021.1

  The reactivity difference of major and minor π-allyl species was examined for two typed asymmetric allylic substitutions via linear symmetrical π-allyl and linear unsymmetrical π-allyl intermediates. 31P NMR observation of the stoichiometric reaction of [Pd(1,3-diphenyl-π -allyl)(N-P-N-type ligand)]+ with malonate ion verified that major species was much more reactive than the minor one. In the case

  通过线性对称π-烯丙基和线性不对称π-烯丙基中间体，对两种类型的不对称烯丙基取代基检测了主要和次要π-烯丙基物种的反应性差异。31 [（NP的Pd（1,3-二苯基-烯丙基π）的化学计量反应的P NMR观察- ñ -型配体）] +与丙二酸离子证实主要种类是比次一个更具有反应性。在[Pd（1,1,3-三甲基-π-烯丙基）（（S）-BINAP）] +物种与软酰胺离子反应的情况下，π-烯丙基物种的次要/主要比率增加给出更高的对映选择性，表明次要的π-烯丙基比主要的π-烯丙基更具反应性。
• Poly-β-peptides from functionalized β-lactam monomers and antibacterial compositions containing same
  申请人：Stahl Shannon S.

  公开号：US09120892B2

  公开（公告）日：2015-09-01

  Disclosed is a method of making β-polypeptides. The method includes polymerizing β-lactam-containing monomers in the presence of a base initiator and a co-initiator which is not a metal-containing molecule to yield the product β-polypeptides. Specifically disclosed are methods wherein the base initiator is potassium t-butoxide, lithium bis(trimethylsilyl)amide (LiN(TMS)2), potassium bis(trimethyl-silyl)amide, and sodium ethoxide, and the reaction is carried out in a solvent such as chloroform, dichloromethane, dimethylsulfoxide, or tetrahydrofuran.

  揭示了一种制备β-多肽的方法。该方法包括在碱引发剂和不是金属含量分子的共引发剂的存在下，聚合含β-内酰胺的单体，从而产生产物β-多肽。具体揭示的方法包括基础引发剂为钾叔丁醇盐、锂双(三甲基硅基)胺(LiN(TMS)2)、双(三甲基硅基)胺钾和乙醇钠，反应在氯仿、二氯甲烷、二甲基亚砜或四氢呋喃等溶剂中进行。
• Nickel‐Catalyzed Switchable Site‐Selective Alkene Hydroalkylation by Temperature Regulation**
  作者：Jia‐Wang Wang、De‐Guang Liu、Zhe Chang、Zhen Li、Yao Fu、Xi Lu

  DOI：10.1002/anie.202205537

  日期：2022.8

  A nickel-catalyzed switchable site-selective alkene hydroalkylation was developed. The selection of reaction temperatures led to protocols that provide regiodivergent hydroalkylated products starting from a single alkene substrate.

  开发了一种镍催化的可切换位点选择性烯烃加氢烷基化反应。反应温度的选择导致提供从单一烯烃底物开始的区域发散性氢化烷基化产物的方案。
• Fluoride-Catalyzed Addition of PhSCF₂SiMe₃ to <i>N</i>-Substituted Cyclic Imides Followed by Radical Cyclization: General Synthetic Strategy of <i>gem</i>-Difluoromethylenated 1-Azabicyclic Compounds
  作者：Teerawut Bootwicha、Duanghathai Panichakul、Chutima Kuhakarn、Samran Prabpai、Palangpon Kongsaeree、Patoomratana Tuchinda、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1021/jo802794u

  日期：2009.5.15

  PhSCF2SiMe3 (1) was found, for the first time, to undergo fluoride-catalyzed nucleophilic difluoro-(phenylsulfanyl)methylation reaction to cyclic imides 2, affording the corresponding adducts 3 in moderate to good yields. Reductive cleavage of the phenylsulfanyl group of N-alkylated adducts 3 with Bu3SnH/AIBN yielded gem-difluoromethylated products 4. Under the same reduction conditions, N-alkenylated and N-alkynylated adducts 3 afforded the corresponding gem-difluoromethylenated 1-azabicyclic compounds 5 and 6 with trans stereoselectivity. These compounds were employed as precursors for preparing substituted gem-difluoromethylenated pyrrolizidinones and indolizidinones 7 and 8 by treatment with Et3SiH/BF3 center dot OEt2, and compounds 9 and 10 by nucleophilic displacement of the hydroxyl group, using organosilanes in the presence of BF3 center dot OEt2. The synthesis of highly substituted gem-difluoromethylenated pyrrolizidines 13 and 14 was also demonstrated.
• Zhang, Jihua; Kissounko, Denis A.; Lee, Sarah E., Journal of the American Chemical Society, 2009, vol. 131, p. 1589 - 1597
  作者：Zhang, Jihua、Kissounko, Denis A.、Lee, Sarah E.、Gellman, Samuel H.、Stahl, Shannon S.

  DOI：——

  日期：——