4-(4-氰基苯基)丁酸甲酯 | 20637-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-氰基苯基)丁酸甲酯
• 英文名称: 4-(3-methoxycarbonylprop-1-yl)benzonitrile
• 英文别名: methyl 4-(4-cyanophenyl)butanoate；γ--buttersaeure-methylester；4-(p-Cyanophenyl)-buttersaeure-methylester；4-(4-Cyanophenyl)butanoic acid methyl ester
• CAS: 20637-03-0
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: LUGWUGOOOXSQFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  334.6±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为产物：
  描述：

  Methyl 3-[(4-cyanophenyl)methylamino]propanoate 在 N-(benzyloxy)-N-(pivaloyloxy)-4-(trifluoromethyl)benzamide 、 三甲胺 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到4-(4-氰基苯基)丁酸甲酯
  参考文献：
  名称：

  通过仲胺的直接氮缺失进行骨骼编辑

  摘要：

  合成化学旨在从简单的原料1建立分子复杂性。然而，尽管具有扩大可访问化学空间2,3的巨大潜力，但施加精确变化以操纵分子骨架本身的连接性的能力仍然有限。在这里，我们报告了一种从有机分子中“删除”氮的反应。我们证明了N -pivaloyloxy- N-烷氧基酰胺是异头酰胺的一个子类，它促进脂肪族仲胺的分子间活化以产生分子内碳-碳偶联产物。机理实验表明，反应通过异二氮烯中间体进行，该中间体将氮原子挤出为二氮，产生短寿命的双自由基，它们迅速偶联形成新的碳-碳键。该反应显示出广泛的官能团耐受性，这使得常规胺合成方案能够转化为碳-碳键结构和环合成的策略。通过在生物活性化合物的合成和骨架编辑中使用该反应突出了这一点。

  DOI：

  10.1038/s41586-021-03448-9

文献信息

• Oxadiazole derivatives as S1P1 receptor agonists
  申请人：Almirall, S.A.

  公开号：EP2210890A1

  公开（公告）日：2010-07-28

  New compounds having the chemical structure of formula (I) or pharmaceutically acceptable salts or N-oxides thereof wherein A is selected from the group consisting of -N-, -O- and -S-; B and C independently are selected from the group consisting of -N- and -O-, with the proviso that at least two of A, B and C are nitrogen atoms; G1 is selected from the group consisting of nitrogen atoms and -CRC- groups, wherein RC represents a hydrogen atom, a halogen atom, a C1-4 alkyl group or a C1-4 alkoxy group; R1 is selected from the group consisting of hydrogen atoms, C1-4 alkyl groups, C1-4 alkoxy groups, C3-4 cycloalkyl groups, and -NRdRe groups wherein Rd and Re are independently selected from hydrogen atoms and C1-4 alkyl groups; R2 and R3 are independently selected from the group consisting of hydrogen atoms and C1-4 alkyl groups; R4, R5 and R7 are independently selected from the group consisting of hydrogen atoms, halogen atoms, C1-4 alkyl groups, C1-4 alkoxy groups and C1-4 haloalkyl groups; R6 represents a C1-4 alkyl group or a C1-4 hydroxyalkyl group; or R6 is selected from the group consisting of -S(O)2-NRaRb groups, -(CRfRg)n-(CRhRi)x-(CRjRk)y-NRaRb groups, -(CH2)n-NRaRb groups, -O-(CH2)n-NRaRb groups, -(CH2)n-COOH groups, -(CH2)n-NRa-CO-Rb' groups, -(CH2)n-NRa-(CH2)p-(NH)q-SO-CH3 groups and -(CH2)n-CO-NRaRb groups, wherein n, p, x and y are each independently integers from 0 to 3, q is 0 or 1, Rf, Rg, Rh, Ri, Rj and Rk independently represent hydrogen atoms or halogen atoms, Rb' is selected from the group consisting of methylsulphonyl groups, C1-4 alkyl groups, C1-4 hydroxyalkyl groups, C1-4 carboxyalkyl groups, and C1-4 haloalkyl groups; Ra and Rb are independently selected from the group consisting of hydrogen atoms, methylsulphonyl groups, C1-4 alkyl groups, C1-4 hydroxyalkyl groups, C1-4 carboxyalkyl groups, and C1-4 haloalkyl groups, or Ra and Rb together with the nitrogen atom to which they are attached form a 4 to 6 membered, saturated heterocyclic group, which contains, as heteroatoms, one or two nitrogen atoms and which is substituted by a carboxyl group or a C1-4 carboxyalkyl group; or Rc together with R6 form a C5-8 carbocyclic ring optionally substituted by - NHR' wherein R' represents a hydrogen atom or a 61-4 carboxyalkyl group.

  新化合物具有化学结构的公式(I)或其药学上可接受的盐或N-氧化物，其中 A选自由-N-，-O-和-S-组; B和C独立地选自- N-和-O-组，但至少两个A，B和C是氮原子; G1选自氮原子和-CRC-基团组，其中RC代表氢原子，卤素原子，C1-4烷基基团或C1-4烷氧基团; R1选自氢原子，C1-4烷基基团，C1-4烷氧基团，C3-4环烷基基团和-NRdRe基团，其中Rd和Re独立地选自氢原子和C1-4烷基基团; R2和R3独立地选自氢原子和C1-4烷基基团; R4，R5和R7独立地选自氢原子，卤素原子，C1-4烷基基团，C1-4烷氧基团和C1-4卤代烷基基团; R6代表C1-4烷基基团或C1-4羟基烷基基团; 或R6选自-S(O)2-NRaRb基团，-(CRfRg)n-(CRhRi)x-(CRjRk)y-NRaRb基团， -(CH2)n-NRaRb基团，-O-(CH2)n-NRaRb基团，-(CH2)n-COOH基团，-(CH2)n-NRa-CO-Rb'基团，-(CH2)n-NRa-(CH2)p-(NH)q-SO-CH3基团和-(CH2)n-CO-NRaRb基团，其中 n，p，x和y分别独立地为0到3的整数， q为0或1， Rf，Rg，Rh，Ri，Rj和Rk独立地代表氢原子或卤素原子， Rb'选自甲磺酰基团，C1-4烷基基团，C1-4羟基烷基基团，C1-4羧基烷基基团和C1-4卤代烷基基团组; Ra和Rb独立地选自氢原子，甲磺酰基团，C1-4烷基基团，C1-4羟基烷基基团，C1-4羧基烷基基团和C1-4卤代烷基基团，或 Ra和Rb与它们连接的氮原子一起形成一个含有4到6个成员的饱和杂环基团，其中作为杂原子，含有一个或两个氮原子，并且被羧基或C1-4羧基烷基基团取代; 或 Rc与R6一起形成一个C5-8碳环戊环，可选择地被-NHR'取代，其中R'代表氢原子或C1-4羧基烷基基团。
• Cross-Coupling Reactions through the Intramolecular Activation of Alkyl(triorgano)silanes
  作者：Yoshiaki Nakao、Masahide Takeda、Takuya Matsumoto、Tamejiro Hiyama

  DOI：10.1002/anie.201000816

  日期：2010.6.14

  Cross‐Si‐ing the Jordan: Cross‐coupling reactions of 2‐(2‐hydroxyprop‐2‐yl)phenyl‐substituted alkylsilanes with a variety of aryl halides proceed in the presence of palladium and copper catalysts. The use of K3PO4 base allows for highly chemoselective alkyl coupling with both primary and secondary alkyl groups (Alk).

  乔丹的交叉反应：2-（2-羟基丙-2-基）苯基取代的烷基硅烷与各种芳基卤化物的交叉偶联反应在钯和铜催化剂的存在下进行。K 3 PO 4碱的使用允许与伯烷基和仲烷基（Alk）都高度化学选择性的烷基偶联。
• [EN] FURANE DERIVATIVES AS INHIBITORS OF ATAD2<br/>[FR] DÉRIVÉS DE FURANE UTILISÉS EN TANT QU'INHIBITEURS D'ATAD2
  申请人：BAYER PHARMA AG

  公开号：WO2017093272A1

  公开（公告）日：2017-06-08

  The invention relates to fur an e derivatives of formula (I) as inhibitors of ATAD2, a process for their preparation and use thereof.

  这项发明涉及到公式(I)的毛皮衍生物作为ATAD2的抑制剂，以及它们的制备过程和使用方法。
• Synthesis of 2‐Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence
  作者：Jakub Koudelka、Tomáš Tobrman

  DOI：10.1002/ejoc.202100464

  日期：2021.6.14

  A methodology for the preparation of 2-substituted cyclobutanones from 2-substituted cyclobutenyl diethyl phosphates is described. Substrates containing electron-donating groups prefer the formation of 2-substituted cyclobutanones, while electron-withdrawing groups facilitate the opening of the cyclobutanone ring. The synthesis of cyclobutenyl sulfides is an additional advantage of this method.

  描述了从 2-取代的环丁烯基磷酸二乙酯制备 2-取代的环丁酮的方法。含有给电子基团的底物倾向于形成 2-取代的环丁酮，而吸电子基团有利于环丁酮环的打开。环丁烯基硫化物的合成是该方法的另一个优点。
• Substituent effects in the mass spectra of some γ- and β-substituted methyl butyrates
  作者：Ian Howe、Dudley H. Williams、David G. I. Kingston、Harvey P. Tannenbaum

  DOI：10.1039/j29690000439

  日期：——

  Results are presented (relative ion abundances, I.P. and A.P. measurements) to illustrate substituent effects in the mass spectra of some γ- and β-substituted methyl butyrates. It is argued that (i)‘sub-decomposition energy’ ions and (ii) competition in the source with fast fragmentation processes are important factors influencing parent/daughter ion ratios, which are then rationalised in terms of the

  给出结果（相对离子丰度，IP和AP测量）以说明某些γ-和β-取代的丁酸甲酯在质谱中的取代基效应。有人认为，（i）“亚分解能”离子和（ii）快速分裂过程中的离子源竞争是影响母/子离子比的重要因素，然后根据这两个因素的变化对其进行合理化处理。取代基。在某些情况下，还引起对过渡态活化能的取代基效应。根据相对AP和频率因子来解释不同能量下的母子比率的变化。讨论了从M +中消除MeOH和McLafferty重排的机理。