(Z)-ethyl 3-(cyclohexylamino)but-2-enoate | 32805-76-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-ethyl 3-(cyclohexylamino)but-2-enoate
• 英文别名: ethyl (Z)-3-(cyclohexylamino)but-2-enoate；ethyl 3-(cyclohexylamino)-2-butenoate；ethyl (2Z)-3-(cyclohexylamino)but-2-enoate；3-Cyclohexylamino-trans-crotonsaeure-ethylester
• CAS: 32805-76-8
• 化学式: C₁₂H₂₁NO₂
• 分子量: 211.304
• InChiKey: PFMZXZYYDKQAOO-KTKRTIGZSA-N

物化性质

• 沸点：
  110-115 °C(Press: 0.35 Torr)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 3-(cyclohexylamino)but-2-enoate 在 三乙酰氧基硼氢化钠 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以87%的产率得到Ethyl 3-(cyclohexylamino)butyrate
  参考文献：
  名称：

  Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters

  摘要：

  Convenient procedures for the chemo- and diastereoselective reduction of beta-enamino esters 1 are described. Both cis- and trans-gamma-amino alcohols 2 or beta-amino esters 3 can be prepared by reduction of beta-enamino esters 1, readily available starting materials, with the use of inexpensive reagents Nali-PrOH or NaHbB(OAc)(3)/AcOH, respectively, and the appropriate reduction conditions. The mechanisms and diastereoselectivities for the reductions are discussed. The relative configurations and conformations of the diastereoisomeric gamma-amino alcohols 2 and beta-amino esters 3 obtained are established by H-1 and C-13 NMR study and unequivocally set by their cyclic derivatives tetrahydro-1,3-oxazines 4.

  DOI：

  10.1021/jo00097a039
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 环己胺 在 碘 作用下， 以 乙腈 为溶剂， 以94%的产率得到(Z)-ethyl 3-(cyclohexylamino)but-2-enoate
  参考文献：
  名称：

  串联 Nenitzescu 反应/亲核芳香取代形成新型吡啶基稠合吲哚骨架

  摘要：

  由Nenitzescu反应制备的两组5-羟基吲哚通过分子内亲核取代转化为以吡啶、呋喃和吲哚为关键组分的多稠环体系。该方法提供了在温和反应条件下从易于获得的前体中获得各种线性和角形吡啶并（呋喃）稠合吲哚骨架的简单途径。

  DOI：

  10.1002/ejoc.202100827

文献信息

• Efficient Synthetic Method for β-Enamino Esters Catalyzed by Yb(OTf)3 under Solvent-Free Conditions
  作者：Ravi Varala、Sreelatha Nuvula、Srinivas R. Adapa

  DOI：10.1071/ch06239

  日期：——

  esters have been synthesized in moderate to excellent yields by reacting 1,3-dicarbonyl compounds with amines in the presence of catalytic amounts of Yb(OTf)3 (2 mol%). The reaction proceeds smoothly at ambient temperature under solvent-free conditions. The catalyst can be recovered and reused.

  在催化量的 Yb(OTf)3 (2 mol%) 存在下，通过 1,3-二羰基化合物与胺反应，以中等至极好的产率合成了多种 β-烯氨基酯。该反应在环境温度下在无溶剂条件下顺利进行。催化剂可以回收再利用。
• A General and Efficient Method for the Preparation of β-Enamino Ketones and Esters Catalyzed by Indium Tribromide
  作者：Zhan-Hui Zhang、Liang Yin、Yong-Mei Wang

  DOI：10.1002/adsc.200505268

  日期：2006.1

  A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide. The reaction proceeds smoothly at room temperature in a short reaction time under solvent-free conditions.

  在催化量的三溴化铟存在下，通过使β-二羰基化合物与胺反应，可以高产率地合成出多种β-烯胺酮和酯。在无溶剂条件下，反应在室温下以短的反应时间平稳地进行。
• Iodine‐Catalyzed Conversion of β‐Dicarbonyl Compounds into β‐Enaminones Within a Minute Under Solvent‐Free Conditions
  作者：Siddhartha Gogoi、Ranjana Bhuyan、Nabin C. Barua

  DOI：10.1080/00397910500290557

  日期：2005.11.1

  Abstract Synthesis of β‐enaminones from β‐dicarbonyl compounds has been achieved in high yields within a minute using primary and aromatic amines and catalytic amounts of iodine under solvent‐free conditions at room temperature.

  摘要 在室温无溶剂条件下，使用伯胺和芳香胺以及催化量的碘，在 1 分钟内以高产率从 β-二羰基化合物合成 β-烯胺酮。
• Zinc Triflate Catalysed Synthesis of β-Enamino Ketones(Esters) under Solvent-Free Conditions
  作者：Chengliang Feng、Shuguang Zhang、Jin Cai、Junqing Chen、Huayou Hu、Min Ji

  DOI：10.3184/174751913x13787959859506

  日期：2013.10

  An efficient and mild procedure is described for the synthesis of a series of β-enamino ketones(esters) from 1,3-dicarbonyl compounds and aliphatic and aromatic amines using zinc triflate as the catalyst.

  描述了使用三氟甲磺酸锌作为催化剂从 1,3-二羰基化合物和脂肪族和芳香族胺合成一系列 β-烯氨基酮（酯）的有效和温和的程序。
• Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate
  作者：Cheng-Liang Feng、Ning-Ning Chu、Shu-Guang Zhang、Jin Cai、Jun-Qing Chen、Hua-You Hu、Min Ji

  DOI：10.2478/s11696-014-0544-8

  日期：2014.1.1

  A novel application of highly stable Fe(OTf)3 as an efficient catalyst for the synthesis of a variety of β-enamino ketones and esters under solvent-free conditions is described. Notably, this protocol of a “green synthesis”, which produced β-enamino ketones and esters by the reaction of a variety of β-dicarbonyl compounds and primary amines, exhibits attractive properties including high yields, short

  描述了一种高度稳定的Fe（OTf）3作为无催化剂条件下合成各种β-烯胺酮和酯的有效催化剂的新型应用。值得注意的是，这种“绿色合成”方案是通过多种β-二羰基化合物与伯胺的反应生成β-烯酮和酯，具有诱人的性能，包括高收率，较短的反应时间，较低的催化剂负载量和化学和区域选择性。另外，催化剂易于从反应系统中回收，并易于重新使用而活性损失最小。