(Z)-methyl 3-(pyrrolidin-1-yl)but-2-enoate | 666857-90-5

• 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)-methyl 3-(pyrrolidin-1-yl)but-2-enoate
• 英文别名: cis-methyl 3-(pyrrolidin-1-yl)but-2-enoate；methyl 3-pyrrolidine-1-yl-but-2-enoate；Methyl-3-(N-pyrrolidinyl)crotonate；methyl (Z)-3-pyrrolidin-1-ylbut-2-enoate
• CAS: 666857-90-5
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: UTIVUPFHBDCEGI-FPLPWBNLSA-N

物化性质

• 沸点：
  245.0±19.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-氯甲基-苯甲酰胺 、 (Z)-methyl 3-(pyrrolidin-1-yl)but-2-enoate 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以71%的产率得到甲基2-[(苯甲酰基氨基)甲基]-3-氧代丁酸酯
  参考文献：
  名称：

  Asymmetric synthesis of optically active methyl-2-benzamido-methyl-3-hydroxy-butyrate by robust short-chain alcohol dehydrogenases from Burkholderia gladioli

  摘要：

  特定的短链醇脱氢酶被发现并用于甲基2-苯甲酰胺基-3-羟基丁酸甲酯的动力学不对称转化，具有优异的立体选择性。

  DOI：

  10.1039/c5cc04652a
• 作为产物：
  描述：

  四氢吡咯 、 乙酰乙酸甲酯 在 montmorillonite clay K₁₀ 作用下， 反应 0.02h， 以95%的产率得到(Z)-methyl 3-(pyrrolidin-1-yl)but-2-enoate
  参考文献：
  名称：

  Synthesis in dry media coupled with microwave irradiation : Application to the preparation of enaminoketones.

  摘要：

  Beta-diketones react with a variety of amines and aminoesters over clay K10 or silica under microwave irradiation in open vessels to give within a few minutes, the corresponding enaminoketones with good yields. According to the reaction conditions acylamines may also result.

  DOI：

  10.1016/s0040-4039(00)60678-0

文献信息

• Substituted tetrahydronaphthaline and analogous compounds
  申请人：Bayer Aktiengellschaft

  公开号：US06586613B1

  公开（公告）日：2003-07-01

  Substituted tetrahydro-naphthalenes and analogous compounds are prepared by reducing or condensing appropriate functional substituents in substituted tetrahydro-naphthalenes and analogous compounds by customary methods and converting functional groups in this manner into the desired groups. The compounds according to the invention are suitable for use as active compounds in pharmaceuticals, in particular in pharmaceuticals for treating arteriosclerosis and also dyslipidaemias.

  通过常规方法，通过还原或缩合替代四氢萘和类似化合物中的适当官能基取代物，并将这种方式中的功能基转化为所需的基团，制备出替代四氢萘和类似化合物。根据本发明的化合物适用于作为药物中的活性成分，特别是适用于治疗动脉硬化和血脂异常的药物。
• New aromatic annulation reaction via a C14 enaminone synthon: synthesis of ‘terpenoid-like chalcones’
  作者：Alain Valla、Benoist Valla、Dominique Cartier、Régis Le Guillou、Roger Labia、Pierre Potier

  DOI：10.1016/j.tetlet.2005.07.141

  日期：2005.9

  Diverse functionalized synthons from a new enaminone are reported. These synthons were easily obtained in a one pot process starting from a compound derived from β-ionone. A new annulation reaction of this C-14 compound with several anions led to new ‘terpenoid-like’ chalcones.

  报道了来自新的烯胺酮的各种功能化的合成子。这些合成子很容易以一锅法从衍生自β-紫罗兰酮的化合物开始获得。这种C-14化合物与几种阴离子的新环化反应产生了新的“类萜样”查耳酮。
• Demonstrating the Synergy of Synthetic, Mechanistic, and Computational Studies in a Regioselective Aniline Synthesis
  作者：Ian W. Davies、Jean-François Marcoux、Jeffery T. Kuethe、Michael D. Lankshear、Jeremy D. O. Taylor、Nancy Tsou、Peter G. Dormer、David L. Hughes、K. N. Houk、Vildan Guner

  DOI：10.1021/jo035677u

  日期：2004.2.1

  Tri- and tetrasubstituted anilines are formed in good to excellent yields by the addition of ketones to vinamidinium salts (up to 98%). The reaction proceeds via the formation of dienone intermediates, which react to form an enamine with the liberated amine. In the case of a nitro, or dimethylaminomethylene substituent, the enamines undergo a facile electrocyclic ring closure to form a cyclohexadiene, which goes on to form anilines with a high degree of selectivity (up to 50:1) with a minor competing pathway proceeding via the enol providing phenols. Competition experiments using isotopic substitution reveal that the rate determining step en route to dienone is enol/enolate addition to the vinamidinium salt, which is characterized by an inverse secondary isotope effect (k(H/D) 0.7-0.9). Computational studies have been used to provide a framework for understanding the reaction pathway. The original proposal for a [1,5]-H shift was ruled out on the basis of the calculations, which did not locate a thermally accessible transition state. The minimum energy conformation of the enamine is such that a facile electrocyclic ring closure is ensured, which is corroborated by the experimental studies. A framework for understanding the reaction pathway is presented.
• KANG, G, J.;CHAN, T. H., J. ORG. CHEM., 1985, 50, N 4, 452-457
  作者：KANG, G, J.、CHAN, T. H.

  DOI：——

  日期：——
• US6586613B1
  申请人：——

  公开号：US6586613B1

  公开（公告）日：2003-07-01