diethyl 2-[4-(bromomethyl)phenyl]propane-1,3-dioate | 863719-40-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diethyl 2-[4-(bromomethyl)phenyl]propane-1,3-dioate
• 英文别名: Diethyl 2-[4-(bromomethyl)phenyl]propanedioate
• CAS: 863719-40-8
• 化学式: C₁₄H₁₇BrO₄
• 分子量: 329.191
• InChiKey: MJGKSMJKDDDEGX-UHFFFAOYSA-N

物化性质

• 沸点：
  375.2±32.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-[4-(bromomethyl)phenyl]propane-1,3-dioate 在 palladium on activated charcoal 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 18.5h， 生成 2-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-malonic acid diethyl ester
  参考文献：
  名称：

  Design and Synthesis of 4-(α-Hydroxymalonyl)phenylalanine as a New Phosphotyrosyl Mimetic and Its Use in Growth Factor Receptor Bound 2 Src-Homology 2 (Grb2 SH2) Domain-Binding Peptides

  摘要：

  A new phosphotyrosyl mimetic 4-(alpha-hydroxymalonyl)phenylalanine and its incorporation into a Grb2 SH2 domain-binding tripeptide are presented. In whole-cell studies using malonyl ethyl ester prodrug derivatives, it was observed that the 4-(alpha-hydroxymalonyl)phenylalanyl-containing peptide exhibited greater efficacy than the nonhydroxylated 4-(malonyl)phenylalanyl-containing congener in blocking the association of Grb2 with activated erbB-2 tyrosine kinase. These results are consistent with de-esterification and at least partial intracellular decarboxylation.

  DOI：

  10.1021/jm050154v
• 作为产物：
  描述：

  二乙基 2-(对苯甲基)丙二酸酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以78%的产率得到diethyl 2-[4-(bromomethyl)phenyl]propane-1,3-dioate
  参考文献：
  名称：

  Design and Synthesis of 4-(α-Hydroxymalonyl)phenylalanine as a New Phosphotyrosyl Mimetic and Its Use in Growth Factor Receptor Bound 2 Src-Homology 2 (Grb2 SH2) Domain-Binding Peptides

  摘要：

  A new phosphotyrosyl mimetic 4-(alpha-hydroxymalonyl)phenylalanine and its incorporation into a Grb2 SH2 domain-binding tripeptide are presented. In whole-cell studies using malonyl ethyl ester prodrug derivatives, it was observed that the 4-(alpha-hydroxymalonyl)phenylalanyl-containing peptide exhibited greater efficacy than the nonhydroxylated 4-(malonyl)phenylalanyl-containing congener in blocking the association of Grb2 with activated erbB-2 tyrosine kinase. These results are consistent with de-esterification and at least partial intracellular decarboxylation.

  DOI：

  10.1021/jm050154v

文献信息

• Iridium‐Catalyzed Intramolecular Asymmetric Allylic Dearomatization of Benzene Derivatives
  作者：Ze‐Peng Yang、Ru Jiang、Qing‐Feng Wu、Lin Huang、Chao Zheng、Shu‐Li You

  DOI：10.1002/anie.201810900

  日期：2018.12.3

  Guided by the mechanistic insights from computational studies, we have developed an Ir‐catalyzed asymmetric intramolecular allylic dearomatization reaction of benzene derivatives. Under the optimized conditions consisting of a readily available Ir catalyst, a series of spiro[4.5]cyclohexadiene compounds were delivered in reasonable yields (up to 79 %) with good enantioselectivity (up to 99 % ee). The

  在计算研究的力学见解的指导下，我们开发了苯衍生物的Ir催化不对称分子内烯丙基烯丙基脱芳香化反应。在由易于获得的Ir催化剂组成的优化条件下，以合理的收率（最高79％）和良好的对映选择性（最高99％ee）提供了一系列螺[4.5]环己二烯化合物。丙二酸酯二酯型取代基的引入是指导苯环亲核反应性的关键策略。
• Design and Synthesis of 4-(α-Hydroxymalonyl)phenylalanine as a New Phosphotyrosyl Mimetic and Its Use in Growth Factor Receptor Bound 2 Src-Homology 2 (Grb2 SH2) Domain-Binding Peptides
  作者：Sang-Uk Kang、Karen M. Worthy、Lakshman K. Bindu、Manchao Zhang、Dajun Yang、Robert J. Fisher、Terrence R. Burke

  DOI：10.1021/jm050154v

  日期：2005.8.1

  A new phosphotyrosyl mimetic 4-(alpha-hydroxymalonyl)phenylalanine and its incorporation into a Grb2 SH2 domain-binding tripeptide are presented. In whole-cell studies using malonyl ethyl ester prodrug derivatives, it was observed that the 4-(alpha-hydroxymalonyl)phenylalanyl-containing peptide exhibited greater efficacy than the nonhydroxylated 4-(malonyl)phenylalanyl-containing congener in blocking the association of Grb2 with activated erbB-2 tyrosine kinase. These results are consistent with de-esterification and at least partial intracellular decarboxylation.