(1-benzyl-pyrrolidin-2-yl)-acetic acid ethyl ester | 139376-75-3

• 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: (1-benzyl-pyrrolidin-2-yl)-acetic acid ethyl ester
• 英文别名: (1-Benzyl-pyrrolidin-2-yl)-essigsaeure-aethylester；ethyl 2-(1-benzyl-2-pyrrolidinyl)acetate；Ethyl 2-(1-benzylpyrrolidin-2-yl)acetate
• CAS: 139376-75-3
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: DJVUPVOYKBTAIH-UHFFFAOYSA-N

物化性质

• 沸点：
  108 °C(Press: 0.02 Torr)
• 密度：
  1.065±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (E)-2-(1-benzylpyrrolidin-2-ylidene)acetate 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以88%的产率得到(1-benzyl-pyrrolidin-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

  摘要：

  The conditions of the Eschenmoser coupling reaction were studied. The formation of the alpha-thioiminium ion was achieved faster in the presence of an additive (Nal) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.081

文献信息

• Ti(IV) promoted 1, 3-dipolar cycloaddition of nitrones to vinyl ethers
  作者：Pau Bayo´n、Pedro de March、Marta Figueredo、Josep Font

  DOI：10.1016/s0040-4020(98)00983-1

  日期：1998.12

  The 1, 3-dipolar cycloaddition of nitrones to vinyl ethers is accelerated by Ti(IV) species. The efficiency of the catalyst parallels its complexation capacity. The use of Ti(iPrO)2Cl2 favours the formation of trans cycloadducts, presumably through an endo bidentate complex, in which the metal atom is simultaneously coordinated to the vinyl ether and to the cyclic nitrone or the Z isomer of the acyclic

  Ti（IV）促进了硝酮与乙烯基醚的1，3-偶极环加成反应。催化剂的效率与其络合能力平行。Ti（i PrO）2 Cl 2的使用有利于反式环加合物的形成，大概是通过内齿二齿配合物形成的，其中金属原子同时与乙烯基醚和环状硝酮或非环状硝酮的Z异构体配位。
• Therapeutic Compounds
  申请人：Katz Jason

  公开号：US20110207711A1

  公开（公告）日：2011-08-25

  The present invention relates to pyrazolopyridines and imidazopyridines which are inhibitors of the kinase PDK1 and are thus useful for the treatment of myeloproliferative disorders or cancer. The compounds are also useful as inhibitors of other kinases such as FGFR3, NTRK3, RP-S6K and WEE1. Furthermore, the present compounds also selectively inhibit microtubule affinity regulating kinase (MARK) and are therefore useful for the treatment or prevention of Alzheimer's disease.

  本发明涉及一种抑制激酶PDK1的吡唑吡啶和咪唑吡啶化合物，因此可用于治疗骨髓增生性疾病或癌症。这些化合物也可用作其他激酶的抑制剂，例如FGFR3、NTRK3、RP-S6K和WEE1。此外，本化合物还具有选择性抑制微管亲和力调节激酶（MARK）的作用，因此可用于治疗或预防阿尔茨海默病。
• Therapeutic compounds
  申请人：Katz Jason

  公开号：US08455477B2

  公开（公告）日：2013-06-04

  The present invention relates to pyrazolopyridines and imidazopyridines which are inhibitors of the kinase PDK1 and are thus useful for the treatment of myeloproliferative disorders or cancer. The compounds are also useful as inhibitors of other kinases such as FGFR3, NTRK3, RP-S6K and WEE1. Furthermore, the present compounds also selectively inhibit microtubule affinity regulating kinase (MARK) and are therefore useful for the treatment or prevention of Alzheimer's disease.

  本发明涉及一种吡唑吡啶和咪唑吡啶，它们是激酶PDK1的抑制剂，因此可用于治疗骨髓增生性疾病或癌症。这些化合物还可用作其他激酶的抑制剂，例如FGFR3、NTRK3、RP-S6K和WEE1。此外，本化合物还能选择性地抑制微管亲和力调节激酶(MARK)，因此可用于治疗或预防阿尔茨海默病。
• Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles
  作者：Richard A. Bunce、Christopher J. Peeples、Paul B. Jones

  DOI：10.1021/jo00032a025

  日期：1992.3

  A one-pot tandem S(N)2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters. Nitrogen-containing rings are prepared by reaction of the omega-halo-2-alkenoate ester with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt. Yields are routinely in the 60-80% range. Experiments are described which elucidate the chronology of the reaction sequences. Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.
• Doyle et al., Journal of the Chemical Society, 1958, p. 4458,4462
  作者：Doyle et al.

  DOI：——

  日期：——