ethyl 3-(4-benzyloxy-3-bromophenyl)propionate | 478706-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3-(4-benzyloxy-3-bromophenyl)propionate
• 英文别名: Ethyl 3-(3-bromo-4-phenylmethoxyphenyl)propanoate
• CAS: 478706-17-1
• 化学式: C₁₈H₁₉BrO₃
• 分子量: 363.251
• InChiKey: IBXSLKMUZYUGBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-benzyloxy-3-bromophenyl)propionate 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 正丁基锂 、 (CuOTf)*toluene 、 氢气 、 caesium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 溶剂黄146 为溶剂， -78.0~110.0 ℃ 、101.33 kPa 条件下， 反应 32.5h， 生成 verbenachalcone
  参考文献：
  名称：

  铜催化的二芳基醚合成在制备马鞭草酮中的应用

  摘要：

  在吡啶中碳酸铯存在下，利用催化铜介导的2-苄氧基溴苯衍生物和2-甲氧基苯酚衍生物的偶合反应，有效地组装了2-羟基-2'-甲氧基二苯基醚。利用该方法可以简明合成马鞭草酚酮，该化合物据报道可增强神经生长因子刺激PC12D细胞中神经突生长的能力。还显示了初始SAR数据。

  DOI：

  10.1016/s0040-4020(02)00915-8
• 作为产物：
  描述：

  对羟基苯丙酸乙酯 在 溴 、 potassium carbonate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 ethyl 3-(4-benzyloxy-3-bromophenyl)propionate
  参考文献：
  名称：

  Effects of a verbenachalcone derivative on neurite outgrowth, inhibition of caspase induction and gene expression

  摘要：

  A verbenachalcone derivative was synthesized and shown to protect N2a cells from caspase induction caused by serum starvation and to enhance the effect of NGF on neurite outgrowth in PC12 cells. As an initial investigation of the compound's mechanism(s) of action, we performed differential gene expression profiling in PC12 cells using oligonucleotide (similar to10,000 gene probes) microarrays. Gene expression patterns were compared in the presence of NGF (2 and 50 ng/mL) and NGF (2 ng/mL) plus the verbenachalcone derivative. Ten genes were significantly (greater than or equal to 2-fold; p less than or equal to 0.05) up-regulated and seven genes were significantly down-regulated in the presence of the compound. These results were independently validated by quantitative real-time PCR for a subset of genes (cathepsin L, sigma-1 receptor and protein tyrosine phosphatase receptor type R). These genes or their protein products may represent useful therapeutic targets for treating neurodegeneration, such as Alzheimer's disease. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.001

文献信息

• Effects of a verbenachalcone derivative on neurite outgrowth, inhibition of caspase induction and gene expression
  作者：Li-An Yeh、Deppa Padmanaban、Pei Ho、Xeuchao Xing、Patricia Rowley、Lee Jae Morse、Roderick V. Jensen、Gregory D. Cuny

  DOI：10.1016/j.bmcl.2004.12.001

  日期：2005.2

  A verbenachalcone derivative was synthesized and shown to protect N2a cells from caspase induction caused by serum starvation and to enhance the effect of NGF on neurite outgrowth in PC12 cells. As an initial investigation of the compound's mechanism(s) of action, we performed differential gene expression profiling in PC12 cells using oligonucleotide (similar to10,000 gene probes) microarrays. Gene expression patterns were compared in the presence of NGF (2 and 50 ng/mL) and NGF (2 ng/mL) plus the verbenachalcone derivative. Ten genes were significantly (greater than or equal to 2-fold; p less than or equal to 0.05) up-regulated and seven genes were significantly down-regulated in the presence of the compound. These results were independently validated by quantitative real-time PCR for a subset of genes (cathepsin L, sigma-1 receptor and protein tyrosine phosphatase receptor type R). These genes or their protein products may represent useful therapeutic targets for treating neurodegeneration, such as Alzheimer's disease. (C) 2004 Elsevier Ltd. All rights reserved.
• Utilization of a copper-catalyzed diaryl ether synthesis for the preparation of verbenachalcone
  作者：Xuechao Xing、Deepa Padmanaban、Li-An Yeh、Gregory D Cuny

  DOI：10.1016/s0040-4020(02)00915-8

  日期：2002.9

  2-Hydroxy-2′-methoxydiphenyl ethers were efficiently assembled utilizing a catalytic copper mediated coupling of 2-benzyloxybromobenzene derivatives and 2-methoxyphenol derivatives in the presence of cesium carbonate in pyridine followed by debenzylation. Utilization of this method allowed for a concise synthesis of verbenachalcone, a compound reported to enhance nerve growth factor's ability to stimulate

  在吡啶中碳酸铯存在下，利用催化铜介导的2-苄氧基溴苯衍生物和2-甲氧基苯酚衍生物的偶合反应，有效地组装了2-羟基-2'-甲氧基二苯基醚。利用该方法可以简明合成马鞭草酚酮，该化合物据报道可增强神经生长因子刺激PC12D细胞中神经突生长的能力。还显示了初始SAR数据。