tert-Butyl(2E)-3-[3-(hydroxymethyl)phenyl]-2-propenoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: tert-Butyl(2E)-3-[3-(hydroxymethyl)phenyl]-2-propenoate
• 英文别名: 3-(3-hydroxymethylphenyl)acrylic acid tert-butyl ester；(E)-tert-butyl 3-(3-(hydroxymethyl)phenyl)acrylate；tert-butyl 3-(3-hydroxymethylphenyl)acrylate；tert-butyl (E)-3-[3-(hydroxymethyl)phenyl]prop-2-enoate
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: ANCKWBNMVJWBOB-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N-苄基-1-苯基-乙胺 、 tert-Butyl(2E)-3-[3-(hydroxymethyl)phenyl]-2-propenoate 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  [EN] NOVEL PYRIMIDINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF CANCER AND FURTHER DISEASES
  [FR] NOUVEAUX DÉRIVÉS PYRIMIDINES ET LEUR UTILISATION DANS LE TRAITEMENT D'UN CANCER ET AUTRES MALADIES

  摘要：

  该发明涉及式（I）的化合物：其中L1、R1、R2、R3、R4和X的定义如描述中所述。本发明还涉及制备这些化合物的方法，含有它们的药物组合物以及它们在治疗疾病（例如癌症）中的用途。

  公开号：

  WO2010133885A1
• 作为产物：
  描述：

  tert-butyl 3-(3-formylphenyl)acrylate 在 sodium tetrahydroborate 、 水 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以86%的产率得到tert-Butyl(2E)-3-[3-(hydroxymethyl)phenyl]-2-propenoate
  参考文献：
  名称：

  Dual inhibitors of inosine monophosphate dehydrogenase and histone deacetylase based on a cinnamic hydroxamic acid core structure

  摘要：

  Small molecules that act on multiple biological targets have been proposed to combat the drug resistance commonly observed for cancer chemotherapy. By combining the structural features of known inhibitors of inosine monophosphate dehydrogense (IMPDH) and histone deacetylase (HDAC), dual inhibitors of IMPDH and HDAC based on the scaffold of cinnamic hydroxamic acid (CHA) have been designed, synthesized, and evaluated in biological assays. Key features, including the linker length, linker functionality, substitution position, and interacting groups, have been explored. Their individual contribution to the inhibitory activities against human IMPDH1 and IMPDH2 as well as HDAC has been assessed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.081

文献信息

• An Enzyme-Labile Safety Catch Linker for Synthesis on a Soluble Polymeric Support
  作者：Uwe Grether、Herbert Waldmann

  DOI：10.1002/1521-3765(20010302)7:5<959::aid-chem959>3.0.co;2-k

  日期：2001.3.2

  allow release of the desired products from the solid support under very mild conditions is of great interest in organic synthesis and combinatorial chemistry. We describe an enzyme-labile safety-catch linker which releases alcohols and amines through i) enzymatic cleavage of an amino group and ii) subsequent lactam formation. The linker group was investigated on different polymeric supports: TentaGel

  在有机合成和组合化学中，对在各种反应条件下稳定并能在非常温和的条件下从固体载体中释放所需产物的新型且广泛适用的连接基团的开发非常感兴趣。我们描述了一种酶不稳定的安全捕捉连接物，其通过以下步骤释放醇和胺：i）氨基的酶促裂解和ii）随后的内酰胺形成。在不同的聚合物载体：TentaGel上研究了连接基团。PEGA，CPG珠和可溶性聚合物POE-6000。通过青霉素G酰基转移酶催化的苯基乙酰胺的裂解和释放的苄胺对邻位邻酯的攻击，从这些接头-聚合物共轭物中释放出2-甲氧基-5-硝基苄醇。模型研究表明，只有在可溶性POE-6000共轭物的情况下，才能实现高产率的裂解。在其他固体支持物的情况下，酶不能进入聚合物基质的内部。研究了POE-6000接头共轭物在Pd0催化的Heck-，Suzuki-和Sonogashira反应以及Mitsunobu反应和环加成反应中各种酯的应用。这些研究证明，该接头在各种反应条件下均稳定，并且酶促方法可在pH
• Pd-Mediated C-C Bond Formation with Olefins and Acetylenes on Solid Support: A Scope and Limitations Study
  作者：Sabine Berteina、Sebastian Wendeborn、Wolfgang K.-D. Brill、Alain De Mesmaeker

  DOI：10.1055/s-1998-22662

  日期：1998.6

  In this paper we report the scope and limitations of Pd(0)-mediated coupling reactions between aromatic iodides linked to a polystyrene resin and terminal acetylenes and olefins (Heck reactions). Optimized reaction conditions were evaluated with a number of different reagents. The optimized reaction conditions were frequently found to be superior to those previously reported in the literature and resulted in excellent yields of the products upon cleavage from the solid phase.

  本文报道了Pd(0)介导的芳基碘化物与聚苯乙烯树脂连接的末端乙炔和烯烃（Heck反应）之间的耦合反应的范围和局限性。通过多种不同试剂评估了优化的反应条件。发现优化的反应条件通常优于文献中之前报道的条件，并在从固相裂解时产生了优异的产物收率。
• Novel Pyrimidine Derivatives and Their Use in the Treatment of Cancer and Further Diseases
  申请人：ASTRAZENECA AB

  公开号：US20150080396A1

  公开（公告）日：2015-03-19

  The invention concerns compounds of Formula (I): wherein L 1 , R 1 , R 2 , R 3 , R 4 and X are as defined in the description. The present invention also relates to processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the treatment of disease, for example cancer.

  本发明涉及式（I）的化合物：其中L1，R1，R2，R3，R4和X如描述中所定义。本发明还涉及制备这些化合物的工艺，含有它们的制药组合物以及它们在治疗疾病，例如癌症中的应用。
• An Enzyme-Labile Safety Catch Linker for Combinatorial Synthesis on a Soluble Polymeric Support
  作者：Uwe Grether、Herbert Waldmann

  DOI：10.1002/(sici)1521-3773(20000502)39:9<1629::aid-anie1629>3.0.co;2-e

  日期：2000.5.2
• Synthesis and applications of tert-alkoxysiloxane linkers in solid-phase chemistry
  作者：Marco M. Meloni、Peter D. White、Duncan Armour、Richard C.D. Brown

  DOI：10.1016/j.tet.2006.10.052

  日期：2007.1

  Straightforward syntheses of two tert-alkoxysilyl chloride functionalised resins 3 and 31 that allow facile attachment of 1 degrees, 2 degrees, 3 degrees alcohols and phenols to the solid-phase have been achieved. Resin 3 displayed useful loading levels (0.7 mmol/g), and it was stable to storage in activated form. Siloxanes from reaction of 3 with alcohols and phenols were compatible with a variety of reaction conditions commonly used in solid-phase synthesis. (c) 2006 Published by Elsevier Ltd.