3-oxo-3-(toluene-4-sulfonylamino)-propionic acid ethyl ester | 145909-26-8

• 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: 3-oxo-3-(toluene-4-sulfonylamino)-propionic acid ethyl ester
• 英文别名: Ethyl 3-oxo-3-(p-tolylsulfonylamino)propanoate；ethyl 3-[(4-methylphenyl)sulfonylamino]-3-oxopropanoate
• CAS: 145909-26-8
• 化学式: C₁₂H₁₅NO₅S
• 分子量: 285.321
• InChiKey: HZUDWYCDJLGGCC-UHFFFAOYSA-N

物化性质

• 熔点：
  97-99 °C
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-oxo-3-(toluene-4-sulfonylamino)-propionic acid ethyl ester 在 盐酸 、 苯磺酰基叠氮化物 、 氢氧化钾 、 sodium ethanolate 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 24.0h， 生成 2-Diazo-N-methyl-N-(4-nitro-phenyl)-3-oxo-3-(toluene-4-sulfonylamino)-propionamide
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1011648303788
• 作为产物：
  描述：

  对甲苯磺酰叠氮 、 丙炔酸乙酯 在 水 、 copper(II) acetate monohydrate 、 2-氨基苯酚 作用下， 以92%的产率得到3-oxo-3-(toluene-4-sulfonylamino)-propionic acid ethyl ester
  参考文献：
  名称：

  钯催化的[3 + 2] -CC / NC形成键

  摘要：

  从共振稳定的乙酰胺和环状α，β-不饱和-γ-氧羰基衍生物开始，公开了掺入吡咯烷酮环的双环和三环结构的合成。该过程涉及分子间的Tsuji-Trost烯丙基化/分子内的氮1,4-加成序列。这种双亲核试剂/双亲电子试剂[3 + 2]的成功成功的关键是其明确定义的步骤时间顺序以及前一步的总化学选择性。当新形成的环状产物在氮取代基上带有适当定位的邻卤代芳基部分时，另一分子内的酮基α-芳基化反应可加入级联反应，从而在同一合成操作中形成两个新的环和三个新的键。

  DOI：

  10.1021/acs.orglett.8b01616

文献信息

• Analogues of the 2-carboxyl-6-hydroxyoctahydroindole (CHOI) unit from diverging Pd-catalyzed allylations: Selectivity as a function of the double bond position
  作者：Zhongyi Mao、Elisabetta Martini、Guillaume Prestat、Julie Oble、Pei-Qiang Huang、Giovanni Poli

  DOI：10.1016/j.tetlet.2017.09.046

  日期：2017.11

  bearing an unsaturation in different positions. Sequential homologation, and epoxidation or syn-dihydroxylation steps were investigated to access analogues of the bicyclic 2-carboxyl-6-hydroxyoctahydroindole motif of aeruginosins, a family of peptides displaying serine protease inhibitor activity.

  钯催化的环状双烯丙基底物的烯丙基化，以两个单独的步骤或以假多米诺方式进行，可以生成在不同位置带有不饱和键的2-羧基-六氢吲哚。为了获得铜绿素酶的双环2-羧基-6-羟基八氢吲哚基序的序列类似物，环氧化或顺-二羟基化步骤进行了研究，这是一个显示丝氨酸蛋白酶抑制剂活性的肽家族。
• Heterocyclic amines useful in the therapy of asthma and imflammation of
  申请人：Boehringer Mannheim Italia S.p.A.

  公开号：US05453423A1

  公开（公告）日：1995-09-26

  Compounds of the formula ##STR1## wherein A, Y, X, B and D are described in the specification are disclosed. The compounds possess activity in treating asthma and other pathologies of the respiratory tract.

  公式为##STR1##的化合物在规范中描述了A、Y、X、B和D。这些化合物具有治疗哮喘和呼吸道其他病变的活性。
• Pd‐Catalyzed [3+2]‐Dehydrogenative Annulation Reactions
  作者：Yang Liu、Mikaël Le Roch、Alessia Mori、Alexandre Pradal、Giovanni Poli、Julie Oble

  DOI：10.1002/ejoc.202300710

  日期：2023.10.9

  Pd-catalyzed [3+2] annulations go dehydrogenative: a new protocol enables the Pd(II)-catalyzed [3+2] annulation between resonance-stabilized acetamides (or 3-oxoglutarates) and β,γ-unsaturated cyclic carbonyl derivatives. This dehydrogenative strategy represents a more atom- and step- economical version than the corresponding Pd(0)-catalyzed redox-neutral couplings previously studied by our group,

  Pd 催化的 [3+2] 环化进行脱氢：一种新方案能够在共振稳定的乙酰胺（或 3-酮戊二酸盐）和 β,γ-不饱和环状羰基衍生物之间进行 Pd(II) 催化的 [3+2] 环化。这种脱氢策略代表了比我们小组之前研究的相应的 Pd(0) 催化氧化还原中性偶联更原子和步骤更经济的版本，使得能够直接构建许多杂多环结构。
• Highly controlling selectivity of copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC) between sulfonyl azids and normal alkynes or propynoates
  作者：Yantao Liu、Xinyan Wang、Jimin Xu、Qun Zhang、Yi Zhao、Yuefei Hu

  DOI：10.1016/j.tet.2011.06.017

  日期：2011.8

  In this article, a combination of Cu(OAc)(2).H(2)O/(2)-aminophenol was developed as a highly efficient and controlling catalytic system for sulfonyl azids involved CuAAC. By using this catalytic system, sulfonyl azids reacted with normal alkynes or propynoates to selectively give the ring products or the chain products, respectively, in excellent yields within minutes. HOAc in situ produced in the reaction has been proved to be a super protonation reagent, by which the unstable intermediate 5-cuprated 1,2,3-triazole was protonated efficiently to yield ring-product 1-sulfonyl 1,2,3-trizoles. The control experiments also proved that 2-aminophenol played dual roles as both ligand and reductant, which led to the cheap and chemically stable Cu(OAc)(2)center dot H(2)O being an efficient copper source for our purpose. (C) 2011 Elsevier Ltd. All rights reserved.
• Ethyl malonate amides: A diketo acid offspring fragment for HIV integrase inhibition
  作者：Katarzyna Serafin、Pawel Mazur、Andrzej Bak、Elodie Laine、Luba Tchertanov、Jean-François Mouscadet、Jaroslaw Polanski

  DOI：10.1016/j.bmc.2011.06.054

  日期：2011.8

  While searching for new HIV integrase inhibitors we discovered that some ethyl malonate amides (EMA) are active against this enzyme. Surprisingly, the main function can only very rarely be found among the reported drug candidates. We synthesised a series of compounds in order to establish and analyse the structure-activity relationship. The similarity to the important classes of HIV integrase inhibitors as well as the synthetic availability of the different targets including this pharmacophore makes EMA compounds an interesting object of investigations. (C) 2011 Elsevier Ltd. All rights reserved.