N-<(E)-2-butenyloxycarbonyl>imidazole | 104208-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-<(E)-2-butenyloxycarbonyl>imidazole
• 英文别名: (E)-But-2-en-1-yl 1H-imidazole-1-carboxylate；[(E)-but-2-enyl] imidazole-1-carboxylate
• CAS: 104208-01-7
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: JGNHUWISNXLDCV-NSCUHMNNSA-N

物化性质

• 沸点：
  266.1±33.0 °C(Predicted)
• 密度：
  1.107 g/mL at 25 °C
• 闪点：
  >110℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  N-<(E)-2-butenyloxycarbonyl>imidazole 、 对溴苯乙酸 以 乙腈 为溶剂， 反应 48.0h， 以84%的产率得到(E)-but-2-en-1-yl 2-(4-bromophenyl)acetate
  参考文献：
  名称：

  Chemoselective Esterification and Amidation of Carboxylic Acids with Imidazole Carbamates and Ureas

  摘要：

  Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields

  DOI：

  10.1021/ol1018882
• 作为产物：
  描述：

  巴豆醇 、 N,N'-羰基二咪唑 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到N-<(E)-2-butenyloxycarbonyl>imidazole
  参考文献：
  名称：

  三氟化硼醚介导的烯丙基 1H-咪唑-1-羧酸酯对酮烯醇酯的 O-酰化一种合成取代烯醇碳酸酯的简便方法

  摘要：

  通过酮烯醇化物与烯丙基 1 H-咪唑-1-羧酸酯和三氟化硼醚合物的配合物的反应，建立了对取代烯丙醇碳酸酯的便捷获取。

  DOI：

  10.1021/jo7016313

文献信息

• Syntheses of (5E)-PGE2 and New 6-Functionalized Derivatives by the Use of Palladium-Catalyzed Decarboxylative Allylic Alkylation
  作者：Toshio Tanaka、Noriaki Okamura、Kiyoshi Bannai、Atsuo Hazato、Satoshi Sugiura、Koji Tomimori、Kenji Manabe、Seizi Kurozumi

  DOI：10.1016/s0040-4020(01)82115-3

  日期：1986.1

  followed by intramolecular palladium-catalyzed decarboxylative allylic alkylation. The (5)-prostaglandin E2 skeleton was also obtained from the β-keto allylic ester (11) by a similar decarboxylative allylic alkylation. The decarboxylative allylic alkylation of another type of the three-component coupling product (12) gave new 6-methyleneprostaglandin E1 skeleton (15a), which was converted into new 6-methylprosta-glandin

  （5 ）-前列腺素E 2（7）由有机铜共轭加成加合物（3）的2-烯氧基氧羰基（1）由（）-4-丁基二甲基甲硅烷氧基-2-环戊烯酮（1）合成，然后通过分子内钯催化的脱羧烯丙基烷基化反应合成。（5 ）-前列腺素E 2骨架也由β-酮烯丙基酯（11）通过类似的脱羧烯丙基烷基化获得。另一种类型的三组分偶联产物（12）的脱羧烯丙基烷基化反应产生了新的6-亚甲基前列腺素E1骨架（15a），将其转化成新的6 methylprosta-glandin我甲酯（20）6-methyleneprostaglandin˚F 1 α衍生物（16由两种不同的方式）。该分子内脱羧烯丙基烷基化的立体化学在2-[（）-或（）-2-丁烯氧基-羰基]环戊酮体系的反应中进行了讨论。
• Stereospecific synthesis of (5)-PGE2 by palladium-catalyzed decarboxylative 2-alkenylation of 2-alkenyloxycarbonylated cyclopentanone derivative
  作者：T. Tanaka、N. Okamura、K. Bannai、A. Hazato、S. Sugiura、K. Manabe、S. Kurozumi

  DOI：10.1016/s0040-4039(01)80891-1

  日期：1985.1

  lopentenone by 2-alkenyloxycarbonylation of the organocopper conjugate-addition adduct followed by intramolecular palladium-catalyzed decarboxylative 2-alkenylation. A ()-2-butenylated cyclopentanone derivative was obtained from either 2-[()- or ()-2-butenyloxy-carbonyl]cyclopentanone derivative under the similar reaction condition.

  （5 ）-前列腺素E 2甲酯是通过（2- ）-4-丁基二甲基甲硅烷氧基-2-环戊烯酮通过有机铜共轭加成加合物的2-链烯基氧羰基化，然后通过分子内钯催化的脱羧2-链烯基化而合成的。A（从任2得到）-2- butenylated环戊酮衍生物- [（ ）-或（）-2-丁烯氧基羰基]相似的反应条件下环戊酮衍生物。
• Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp³–sp³ Coupling
  作者：Timothy J. McClure、Connor Saludares、Gisela Martinez、Cheyenne Orozco、Raul Navarro

  DOI：10.1021/acs.joc.2c00723

  日期：2022.6.3

  A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and decarboxylation under mild reaction conditions, a process facilitated by the formation of a stabilized aromatic anion. The regioselective allylic coupling

  已经开发出用于钯催化的脱羧烯丙基烷基化反应的新的稳定苄基亲核试剂家族。发现衍生自 3-羧基苯酞的烯丙酯在温和的反应条件下经历了钯催化的脱烯丙基化和脱羧反应，该过程通过形成稳定的芳族阴离子来促进。该中间体的区域选择性烯丙基偶联以 73-96% 的产率提供了多种功能化的苯酞。
• On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents
  作者：Stephen T. Heller、Richmond Sarpong

  DOI：10.1016/j.tet.2011.09.057

  日期：2011.11

  The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of alpha,beta-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids. (C) 2011 Elsevier Ltd. All rights reserved.
• Direct N-Carbamoylation of 3-Monosubstituted Oxindoles with Alkyl Imidazole Carboxylates
  作者：Barry M. Trost、Yong Zhang、Ting Zhang

  DOI：10.1021/jo900760r

  日期：2009.7.17

  Regioselective N-carbamoylation of oxindoles was achieved through the use of imidazole carboxylate reagents. This reaction provides ready access to N-carbamoyl-3-monosubstituted oxindoles.