4-丙酰基-2,2-二甲基丙酸苯酯 | 120703-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-丙酰基-2,2-二甲基丙酸苯酯
• 英文名称: p-(trimethylacetoxy)propiophenone
• 英文别名: 4'-pivalolyl propiophenone；4-Propanoylphenyl 2,2-dimethylpropanoate；(4-propanoylphenyl) 2,2-dimethylpropanoate
• CAS: 120703-45-9
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: CZDYREYTQIPCTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2915900090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  4-丙酰基-2,2-二甲基丙酸苯酯 在 溴 、 sodium sulfite 作用下， 以 乙醚 、 水 为溶剂， 反应 1.08h， 以100%的产率得到2,2-dimethyl-propanoic acid 4-(1-oxo-2-bromo-propyl)phenyl ester
  参考文献：
  名称：

  GLUCOPYRANOSIDES CONJUGATES OF 2-(4-HYDROXY-PHENYL)-1- 4-(2-AMIN-1-YL-ETHOXY)-BENZYL]-1H-INDOL-5-OLS

  摘要：

  公开号：

  EP1212335B1
• 作为产物：
  描述：

  三甲基乙酰氯 、 4-羟基苯丙酮 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.0h， 以100%的产率得到4-丙酰基-2,2-二甲基丙酸苯酯
  参考文献：
  名称：

  修饰侧链的二茂铁基三苯氧胺衍生物的合成及构效关系

  摘要：

  我们在此报告乳腺癌药物他莫昔芬衍生物的合成和细胞增殖特性，其中负责该药物抗雌激素特性的O（CH 2）2 N（CH 3）2侧链已被α二茂铁基部分。我们最近报道的二酚化合物5，其中该氨基酸链已被替换为酰基二茂铁（ O（CH 2）2 C（O）[（η 5 -C 5 H ^ 4）（FeCp]）组，并且对激素依赖性MCF-7和非依赖性MDA-MB-231乳腺癌细胞系均具有抗增殖作用。现在，我们报告结构-活性关系（SAR）研究的结果，其中侧链长度已变化，酮基已被省略，苯酚基团的数目已变化。化合物1 - 4，具有侧链缺乏羰基函数（ O（CH 2）Ñ [（η 5 -C 5 H ^ 4）FeCp]，Ñ= 1–4），并且随着链长的增加，其对ERα的亲和力降低（ER =雌激素受体），对MCF-7细胞起雌激素作用，对PC-3前列腺癌细胞起轻度细胞毒性作用，IC 50值约为10 μ中号。的两个单酚类衍生物2，2

  DOI：

  10.1002/chem.200801108

文献信息

• A facile transformation of alkyl aryl ketones to methyl α-arylalkanoates by anodic oxidation in the presence of iodine or iodo compounds
  作者：Tatsuya Shono、Yoshihiro Matsumura、Susumu Katoh、Tetsuhiro Fujita、Tohru Kamada

  DOI：10.1016/s0040-4039(00)95205-5

  日期：1989.1

  Anodic oxidation of easily accessible alkyl aryl ketones in trimethyl orthoformate containing a small amount of iodine or organo-iodo compounds gave methyl α-arylalkanoates in high yields.

  在含有少量碘或有机碘化合物的原甲酸三甲酯中，容易获得的烷基芳基酮进行阳极氧化，可以高收率得到α-芳基链烷酸甲酯。
• Design and Synthesis of Norendoxifen Analogues with Dual Aromatase Inhibitory and Estrogen Receptor Modulatory Activities
  作者：Wei Lv、Jinzhong Liu、Todd C. Skaar、David A. Flockhart、Mark Cushman

  DOI：10.1021/jm501218e

  日期：2015.3.26

  Both selective estrogen receptor modulators and aromatase inhibitors are widely used for the treatment of breast cancer. Compounds with both aromatase inhibitory and estrogen receptor modulatory activities could have special advantages for treatment of breast cancer. Our previous efforts led to the discovery of norendoxifen as the first compound with dual aromatase inhibitory and estrogen receptor binding activities. To optimize its efficacy and aromatase selectivity versus other cytochrome P450 enzyme, a series of structurally related norendoxifen analogues were designed and synthesized. The most potent compound, 4'-hydroxynorendoxifen (10), displayed elevated inhibitory potency against aromatase and enhanced affinity for estrogen receptors when compared to norendoxifen. The selectivity of 10 for aromatase versus other cytochrome P450 eniymes was also superior to norendoxifen. 4'-Hydroxynorendoxifen is therefore an interesting lead for further development to obtain new anticancer agents of potential value for the treatment of breast cancer.
• Organometallic analogues of tamoxifen: Effect of the amino side-chain replacement by a carbonyl ferrocenyl moiety in hydroxytamoxifen
  作者：Anh Nguyen、Siden Top、Anne Vessières、Pascal Pigeon、Michel Huché、Elizabeth A. Hillard、Gérard Jaouen

  DOI：10.1016/j.jorganchem.2006.11.016

  日期：2007.2

  Since the widely prescribed selective estrogen receptor modulator (SERM) tamoxifen encounters growing cases of resistance in long-term treatments, alternative drugs with different therapeutic scopes have to be developed. Many investigators have modified the triphenylethylene scaffold, but very few have changed its amino side chain, essential for the antiestrogenic activity. For the first time, a lipophilic and stable organometallic entity, -OCH2CO-[(eta(5)-C5H4)FeCp], has replaced this key functional side chain, while keeping a good affinity for the estrogen receptor and an antiproliferative activity on cancer cells (MCF-7 and PC-3). Its mechanism of action is likely to be different from the antihormonal pathway followed by hydroxytamoxifen, and from the cytotoxicity observed for the ferrocifens. (C) 2006 Elsevier B.V. All rights reserved.