乙基7-(4-甲氧基苯基)-7-氧代庚酸酯 | 122115-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙基7-(4-甲氧基苯基)-7-氧代庚酸酯
• 英文名称: ethyl 7-(4-methoxyphenyl)-7-oxoheptanoate
• CAS: 122115-54-2
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: PHAFJUYPYMREHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  乙基7-(4-甲氧基苯基)-7-氧代庚酸酯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 7-(4-甲氧基苯基)-7-恶庚烷
  参考文献：
  名称：

  Structurally Simple Trichostatin A-Like Straight Chain Hydroxamates as Potent Histone Deacetylase Inhibitors

  摘要：

  A series of new, structurally simple trichostatin A (TSA)-like straight chain hydroxamates were prepared and evaluated for their ability to inhibit partially purified human histone deacetylase 1 (HDAC-1). Some of these compounds such as 8m, 8n, 12, and 15b exhibited potent HDAC inhibitory activity with low nanomolar IC50 values, comparable to natural TSA. These compounds induce hyperacetylation of histones in T24 human cancer cells and significantly inhibit proliferation in. various human cancer cells. They also induce expression of p21 and cause cell cycle blocks in human cancer cells. in this paper, we describe the synthesis of these new compounds as well as structure-activity relationship results from enzyme inhibition and alterations in cellular function.

  DOI：

  10.1021/jm020154k
• 作为产物：
  描述：

  6-溴己酸乙酯 、 对甲氧基苯甲酰氯 在 三甲基氯硅烷 、 indium acetylacetonate 、 lithium chloride 、 锌 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 1,2-二溴乙烷 为溶剂， 反应 5.0h， 以250 mg的产率得到乙基7-(4-甲氧基苯基)-7-氧代庚酸酯
  参考文献：
  名称：

  通过InX3和LiCl催化的将锌插入芳基和杂芳基碘化物和溴化物中来制备多功能有机卤化锌

  摘要：

  由InCl 3（3 mol％）和LiCl（30 mol％）组成的催化体系可通过将锌粉插入THF中的各种芳基碘化物中，在50°C下以高达95％的产率方便地制备多官能芳基卤化锌。使用THF / DMPU（1：1）混合物可缩短反应速率，并允许制备酮基取代的芳基锌试剂。在In（acac）3（3 mol％）和LiCl（150 mol％）的存在下，锌顺利插入到各种芳基和杂芳基溴化物中（50°C，2-18 h）。在In（acac）3（10 mol％）和LiCl（150 mol％）存在下，烷基溴化物也转化为相应的锌试剂，产率为70-80％。

  DOI：

  10.1002/chem.201605139

文献信息

• Structurally Simple Trichostatin A-Like Straight Chain Hydroxamates as Potent Histone Deacetylase Inhibitors
  作者：Soon Hyung Woo、Sylvie Frechette、Elie Abou Khalil、Giliane Bouchain、Arkadii Vaisburg、Naomy Bernstein、Oscar Moradei、Silvana Leit、Martin Allan、Marielle Fournel、Marie-Claude Trachy-Bourget、Zuomei Li、Jeffrey M. Besterman、Daniel Delorme

  DOI：10.1021/jm020154k

  日期：2002.6.1

  A series of new, structurally simple trichostatin A (TSA)-like straight chain hydroxamates were prepared and evaluated for their ability to inhibit partially purified human histone deacetylase 1 (HDAC-1). Some of these compounds such as 8m, 8n, 12, and 15b exhibited potent HDAC inhibitory activity with low nanomolar IC50 values, comparable to natural TSA. These compounds induce hyperacetylation of histones in T24 human cancer cells and significantly inhibit proliferation in. various human cancer cells. They also induce expression of p21 and cause cell cycle blocks in human cancer cells. in this paper, we describe the synthesis of these new compounds as well as structure-activity relationship results from enzyme inhibition and alterations in cellular function.
• Preparation of Polyfunctional Organozinc Halides by an InX₃- and LiCl-Catalyzed Zinc Insertion to Aryl and Heteroaryl Iodides and Bromides
  作者：Andreas D. Benischke、Grégoire Le Corre、Paul Knochel

  DOI：10.1002/chem.201605139

  日期：2017.1.18

  of zinc powder to various aryl iodides in THF at 50 °C in up to 95 % yield. The use of a THF/DMPU (1:1) mixture shortens the reaction rates and allows the preparation of keto‐substituted arylzinc reagents. In the presence of In(acac)3 (3 mol %) and LiCl (150 mol %), the zinc insertion to various aryl and heteroaryl bromides proceeds smoothly (50 °C, 2–18 h). Alkyl bromides are also converted to the

  由InCl 3（3 mol％）和LiCl（30 mol％）组成的催化体系可通过将锌粉插入THF中的各种芳基碘化物中，在50°C下以高达95％的产率方便地制备多官能芳基卤化锌。使用THF / DMPU（1：1）混合物可缩短反应速率，并允许制备酮基取代的芳基锌试剂。在In（acac）3（3 mol％）和LiCl（150 mol％）的存在下，锌顺利插入到各种芳基和杂芳基溴化物中（50°C，2-18 h）。在In（acac）3（10 mol％）和LiCl（150 mol％）存在下，烷基溴化物也转化为相应的锌试剂，产率为70-80％。