N-phenylcyclopent-3-ene-1-carboxamide | 7686-79-5

• 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: N-phenylcyclopent-3-ene-1-carboxamide
• 英文别名: 3-Cyclopenten-1-carbonsaeure-anilid；N-Phenyl-3-cyclopentene-1-carboxamide
• CAS: 7686-79-5
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: QGQXPSKFLSZDRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-phenylcyclopent-3-ene-1-carboxamide 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 4,4,6-trimethyl-1,3,2-dioxaborinane 、 N-benzyl-N-phenyl-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-amine 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到(1R,3S)-3-hydroxycyclopentanecarboxylic acid phenyl amide
  参考文献：
  名称：

  Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki–Miyaura Cross-Coupling

  摘要：

  The rhodium-catalyzed enantioselective desymmetrization of symmetric gamma,delta-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral gamma-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

  DOI：

  10.1021/ol503764d
• 作为产物：
  描述：

  环戊-3-烯-1,1-二羧酸 在 氯化亚砜 作用下， 以 乙醚 为溶剂， 生成 N-phenylcyclopent-3-ene-1-carboxamide
  参考文献：
  名称：

  A New Route to 1-Substituted 3-Cyclopentenes

  摘要：

  DOI：

  10.1021/jo01054a027

文献信息

• Merging Photoredox PCET with Ni-Catalyzed Cross-Coupling: Cascade Amidoarylation of Unactivated Olefins
  作者：Shuai Zheng、Álvaro Gutiérrez-Bonet、Gary A. Molander

  DOI：10.1016/j.chempr.2018.11.014

  日期：2019.2

  integration of amidyl radicals with cross-coupling chemistry opens new avenues for reaction design. However, the lack of efficient methods for the generation of such radical species has prevented many such transformations from being brought to fruition. Herein, the amidoarylation of unactivated olefins by a cascade process from non-functionalized amides is reported by merging, for the first time, photoredox

  酰胺基自由基与交叉偶联化学的整合为反应设计开辟了新途径。然而，缺乏产生此类自由基物种的有效方法阻止了许多此类转化的实现。在本文中，首次报道了通过光氧化还原质子偶联电子转移（PCET）与镍催化的合并，通过级联法从非官能化酰胺进行的未活化烯烃的酰胺化。这项新技术可以在可见光催化剂和镍催化剂的存在下，从烯基酰胺，芳基和杂芳基卤化物中获得一系列包含特权吡咯烷酮核心的复杂分子。值得注意的是，该反应不限于酰胺-也可以使用氨基甲酸酯和脲。机理研究，
• Chromium-Catalyzed Ligand-Free Amidation of Esters with Anilines
  作者：Changpeng Chen、Liang Ling、Meiming Luo、Xiaoming Zeng

  DOI：10.1246/bcsj.20200277

  日期：2021.3.15

  Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available es...

  由于有趣的生物活性特性，酰胺是药物和农业化学化学中的重要结构基序。我们在此报告市售 es 的酰胺化...
• Chromium-Catalyzed Activation of Acyl C–O Bonds with Magnesium for Amidation of Esters with Nitroarenes
  作者：Liang Ling、Changpeng Chen、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/acs.orglett.9b00554

  日期：2019.3.15

  chromium-catalyzed activation of acyl C–O bonds with magnesium for amidation of esters with nitroarenes. Low-cost chromium(III) chloride shows high reactivity in promoting amidation by using magnesium as reductant and chlorotrimethylsilane as additive. It provides a step-economic strategy to the synthesis of centrally important amide motifs using inexpensive and air-stable nitroarenes as amino sources.

  在这里，我们报道了铬与镁催化的羰基C–O键活化，从而使酯与硝基芳烃酰胺化。通过使用镁作为还原剂和氯代三甲基硅烷作为添加剂，低成本的氯化铬（III）在促进酰胺化方面显示出高反应活性。它为使用廉价且空气稳定的硝基芳烃作为氨基源合成重要的酰胺基序提供了分步经济策略。
• Rhodium-Catalyzed Desymmetrization by Hydroformylation of Cyclopentenes: Synthesis of Chiral Carbocyclic Nucleosides
  作者：Cai You、Biao Wei、Xiuxiu Li、Yusheng Yang、Yue Liu、Hui Lv、Xumu Zhang

  DOI：10.1002/anie.201601478

  日期：2016.5.23

  Excellent enantioselectivities (up to 97 % ee) and diastereoselectivities (up to >99:1 d.r.) have been achieved in the desymmetrization of cyclopentenes by catalytic hydroformylation. This novel methodology provides an efficient and concise synthetic route to chiral cyclopentane carboxaldehydes. The key intermediate, (1S,3S)‐(3‐hydroxymethyl)cyclopentanol, for the synthesis of carbocyclic‐ddA was obtained

  在通过催化加氢甲酰化进行环戊烯的不对称化反应中，已实现了出色的对映选择性（高达97％ee）和非对映选择性（高达> 99：1 dr）。这种新颖的方法为手性环戊烷羧酸醛的合成提供了一种有效而简洁的方法。通过三个步骤获得了用于合成碳环-ddA的关键中间体（1 S，3 S）-（3-羟甲基）环戊醇。
• Eine Ni0-induzierte CC-kupplungsreaktion von phenylisocyanat mit cyclopenten in gegenwart von chiralen phosphor-liganden
  作者：A. Tillack、R. Selke、Ch. Fischer、D. Bilda、K. Kortus

  DOI：10.1016/0022-328x(96)06149-9

  日期：1996.7

  In the presence of chiral phosphite- and phosphonite-Ni-0-systems, cyclopentene reacts with phenylisocyanate to give optically active 2-cyclopentene-1-carboxanilide (2) by CC-coupling. Enantiomeric excesses of up to 13% have been obtained so far.As a competitive reaction, an isomerization of 2 occurs; this gives rise to a decrease in regioselectivity, The isomeric distribution in the final product mixture clearly shows a relationship between the tendency of isomerization and the basicity of the P-ligands.The product distribution, as well as the determination of enantiomeric excess, took place on GC, and the enantiomeric separation took place on HPLC.