3-(3-Cyano-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester | 325481-36-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(3-Cyano-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester
• 英文别名: Methyl 3-(3-cyanophenyl)-2-(1,3-dioxoisoindol-2-yl)propanoate
• CAS: 325481-36-5
• 化学式: C₁₉H₁₄N₂O₄
• 分子量: 334.331
• InChiKey: FUUDPVHEDGDRRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3-Cyano-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester 在 palladium on activated charcoal 氢气 、 乙酸肼 、 碳酸氢钠 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 生成 2-(2-Amino-acetylamino)-3-[3-(tert-butoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester
  参考文献：
  名称：

  Bivalent inhibition of β-Tryptase: distance scan of neighboring subunits by dibasic inhibitors

  摘要：

  Based on bifunctional diketopiperazines as templates and m-aminomethyl-phenylalanine as arginine mimetic, we have synthesized a new class of structurally related dibasic tryptase inhibitors with systematically increasing spacer length. These compounds were used to scan the distance between the active sites of two neighboring subunits of the beta-tryptase tetramer. The K-i-values obtained are a function of the distance between the terminal amino groups and indicate optimal binding of inhibitors with 29-31 bonds between the amino groups. These experimental data are in full agreement with predictions derived from a novel modeling program that allows the docking of bivalent ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00063-x
• 作为产物：
  描述：

  3-氰基苯丙氨酸 在 氯化亚砜 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(3-Cyano-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Bivalent inhibition of β-Tryptase: distance scan of neighboring subunits by dibasic inhibitors

  摘要：

  Based on bifunctional diketopiperazines as templates and m-aminomethyl-phenylalanine as arginine mimetic, we have synthesized a new class of structurally related dibasic tryptase inhibitors with systematically increasing spacer length. These compounds were used to scan the distance between the active sites of two neighboring subunits of the beta-tryptase tetramer. The K-i-values obtained are a function of the distance between the terminal amino groups and indicate optimal binding of inhibitors with 29-31 bonds between the amino groups. These experimental data are in full agreement with predictions derived from a novel modeling program that allows the docking of bivalent ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00063-x

文献信息

• Dual Ligand-Enabled Nondirected C–H Cyanation of Arenes
  作者：Hao Chen、Arup Mondal、Philipp Wedi、Manuel van Gemmeren

  DOI：10.1021/acscatal.8b04639

  日期：2019.3.1

  structural units in organic chemistry and, therefore, highly attractive targets for C–H activation. Herein, the development of an arene-limited, nondirected C–H cyanation based on the use of two cooperatively acting commercially available ligands is reported. The reaction enables the cyanation of arenes by C–H activation in the absence of directing groups and is therefore complementary to established

  芳香腈是有机化学中的关键结构单元，因此是C–H活化的极具吸引力的目标。在此，据报道，基于使用两种可协同作用的市售配体，开发了一种受芳烃限制的，无方向性的CH氰基氰化反应。该反应可在没有导向基团的情况下通过C–H活化使芳烃氰化，因此可与已建立的方法互补。