(E)-3-(4-tert-Butyl-phenyl)-acryloyl chloride | 78974-03-5

• 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: (E)-3-(4-tert-Butyl-phenyl)-acryloyl chloride
• 英文别名: 3-(4-Tert-butylphenyl)prop-2-enoyl chloride
• CAS: 78974-03-5
• 化学式: C₁₃H₁₅ClO
• mdl: MFCD11108006
• 分子量: 222.715
• InChiKey: IEBJAFJYVRUQCO-UHFFFAOYSA-N

物化性质

• 沸点：
  302.5±11.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-tert-Butyl-phenyl)-acryloyl chloride 在 一水合肼 作用下， 以 乙腈 为溶剂， 生成 C₁₃H₁₈N₂O
  参考文献：
  名称：

  光诱导脱氨基 [3 + 2] 环化反应实现 γ-内酰胺的高度非对映选择性合成

  摘要：

  描述了用于合成官能化 γ-内酰胺的N-氨基吡啶鎓盐与烯烃的光引发脱氨基 [3 + 2] 环化反应。这种转变显示出良好的官能团耐受性以及出色的非对映选择性。初步研究表明，所采用的N-氨基吡啶鎓盐通过光诱导单电子转移 (SET) 过程通过 N-N 键断裂产生关键的酰胺基自由基中间体。酰胺基自由基物质将添加到烯烃的双键上，然后进行自由基介导的环化过程，以提供所需的 γ-内酰胺。

  DOI：

  10.1021/acs.orglett.2c01565
• 作为产物：
  描述：

  ethyl 3-(4-t-butylphenyl) propenoate 在 草酰氯 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-3-(4-tert-Butyl-phenyl)-acryloyl chloride
  参考文献：
  名称：

  ACT-451840的发现和表征：一种具有新型作用机制的抗疟药。

  摘要：

  世界上超过40％的人口处于感染疟疾的危险中。大多数疟疾病例发生在撒哈拉以南非洲，中美洲和南美洲以及亚洲的国家。对包括青蒿素组合在内的标准疗法的抵抗力正在增强。迫切需要具有新作用机制的新型抗疟药。在表型筛选中，我们鉴定了一系列基于苯丙氨酸的化合物，它们通过新的但未知的作用机理表现出抗疟活性。我们的优化工作最终决定了ACT-451840 [（S，E）-N-（4-（4-乙酰基哌嗪-1-基）苄基）-3-（4-（叔丁基）苯基）-N- （1-（4-（4-c氰基苄基）哌嗪-1-基）-1-氧代-3-苯基丙烷-2-基）丙烯酰胺用于临床开发。

  DOI：

  10.1002/cmdc.201600298

文献信息

• Palladium-Catalyzed Alkoxycarbonylation of Terminal Alkenes To Produce α,β-Unsaturated Esters: The Key Role of Acetonitrile as a Ligand
  作者：Andrei V. Malkov、Nolwenn Derrien、Maciej Barłóg、Pavel Kočovský

  DOI：10.1002/chem.201304798

  日期：2014.4.14

  A mild protocol has been developed for the PdII‐catalyzed alkoxycarbonylation of terminal olefins to produce α,β‐unsaturated esters with a wide range of substrates. Key features are the use of MeCN as solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O2, which facilitates the CuII‐mediated reoxidation of the Pd0 complex to PdII and prevents

  已开发出一种温和的方案，用于末端烯烃的Pd II催化的烷氧羰基化反应，以生产具有多种底物的α，β-不饱和酯。关键特征是使用MeCN作为溶剂（和/或配体）来控制中间Pd配合物的反应性，以及CO与O 2的组合，这有助于Cu II介导的Pd 0配合物向Pd II和Pd II的再氧化。防止双羰基化。
• <i>N</i>-(ω-(4-(2-Methoxyphenyl)piperazin-1-yl)alkyl)carboxamides as Dopamine D₂ and D₃ Receptor Ligands
  作者：Anneke Hackling、Robin Ghosh、Sylvie Perachon、André Mann、Hans-Dieter Höltje、Camille G. Wermuth、Jean-Charles Schwartz、Wolfgang Sippl、Pierre Sokoloff、Holger Stark

  DOI：10.1021/jm030836n

  日期：2003.8.1

  dopamine D(2) and D(3) receptor ligands were developed from their potentially bioactive conformation and were compared in order to get insight into molecular properties of importance for D(2)/D(3) receptor selectivity. For the 72 compounds presented here, an extended and more linear conformation in the aliphatic or aryl spacers turned out to be crucial for dopamine D(3) receptor selectivity. Structural

  多巴胺D（3）受体被认为是治疗各种神经系统疾病和精神疾病的潜在治疗靶标。针对高亲和力和D（3）与D（2）受体优先的配体，部分激动剂BP 897被视为前导结构。间隔基和芳基部分的变化导致N-烷基化的1-（2-甲氧基苯基）哌嗪具有显着改善的亲和力和选择性。分子建模研究支持结构的发展。多巴胺D（2）和D（3）受体配体的药理模型是从它们潜在的生物活性构象发展而来的，并进行了比较，以便深入了解对于D（2）/ D（3）受体选择性重要的分子特性。对于此处介绍的72种化合物，脂族或芳基间隔基中的扩展和更线性的构象原来是对多巴胺D（3）受体选择性至关重要。芳基部分（苯甲酰胺，杂芳基酰胺，芳基酰亚胺）的结构多样性对（亚）纳摩尔D（3）受体亲和力有重大影响，这是通过更刚性的芳基丙烯酰胺衍生物进行优化的。化合物38（ST 280，（E）-4-碘-N-（4-（4-（2-（甲氧基苯基）哌嗪-1-基）丁基）肉桂酰胺）显
• Inter- and intra-molecular selectivity in the cyclisation of N-cinnamoyl-1-naphthamides in solid-state photochemistry and peri selectivity in their photocyclisation in solution
  作者：Shigeo Kohmoto、Takashi Kobayashi、Takehiko Nishio、Ikuo Iida、Keiki Kishikawa、Makoto Yamamoto、Kazutoshi Yamada

  DOI：10.1039/p19960000529

  日期：——

  The photocyclisation of N-cinnamoyl-1-naphthamides 1a–f was examined in the solid state and in solution. Three types of cyclisation, intramolecular 2π+ 2π and 4π+ 2π, and intermolecular 2π+ 2π cyclisations were observed in the solid state. The ratios of these products were largely dependent on the substituents at the para-position of the cinnamoyl moiety. Single-crystal X-ray crystallographic analysis of 1b showed that the intermolecular distance between the two double bonds was 4.34 Å. Amides with bulky substituents preferred intramolecular 2π+ 2π cyclisation. In contrast to the solid-state photochemistry, only intramolecular cyclisation was observed in solution. The ratios of 2π+ 2π and 4π+ 2π cyclisation products were irradiation time dependent. It was found that the 2π+ 2π cycloreversion and rearrangement from the 2π+ 2π product to the endo 4π+ 2π isomer were the cause of this dependency.

  研究人员考察了 N-肉桂酰基-1-萘甲酰胺 1a-f 在固态和溶液中的光环化现象。在固态下观察到了三种类型的环化：分子内 2π+ 2π 和 4π+ 2π，以及分子间 2π+ 2π 环化。这些产物的比例在很大程度上取决于肉桂酰基对位的取代基。1b 的单晶 X 射线晶体分析表明，两个双键之间的分子间距为 4.34 Å。与固态光化学不同，在溶液中只观察到分子内环化现象。2π+ 2π 和 4π+ 2π 环化产物的比例与辐照时间有关。研究发现，2π+ 2π 环化和从 2π+ 2π 产物到内 4π+ 2π 异构体的重排是造成这种依赖性的原因。
• The design, synthesis and in vitro immunosuppressive evaluation of novel isobenzofuran derivatives
  作者：Na Yang、Qing-He Wang、Wen-Qian Wang、Jian Wang、Feng Li、Shen-Peng Tan、Mao-Sheng Cheng

  DOI：10.1016/j.bmcl.2011.11.078

  日期：2012.1

  The synthesis and biological evaluation of a series of novel isobenzofuran-based compounds are described. The compounds were evaluated for their immunosuppressive effects of T-cell proliferation and IMPDH type II inhibitor activity in vitro, as well as their structure-activity relationships were assessed. Several compounds demonstrated highly efficacious immunosuppressive properties, especially compounds 2d, 2e, 2h and 2j, which were superior to MPA, while compounds 2k, 2m, 2n, 4c and 5d exhibited an equipotent inhibitory activity compared to MPA. Generally, it was obviously demonstrated that alpha,beta-unsaturated amides proved more potent than the diamide and urea series. The present study provides a guide for further research on development of safe and effective immunosuppressive agents. (C) 2011 Elsevier Ltd. All rights reserved.
• Natural product-based design, synthesis and biological evaluation of Albiziabioside A derivatives that selectively induce HCT116 cell death
  作者：Gaofei Wei、Shanshan Cui、Weijing Luan、Shuai Wang、Zhuang Hou、Yongxiang Liu、Yang Liu、Maosheng Cheng

  DOI：10.1016/j.ejmech.2015.12.034

  日期：2016.5

  A series of Albiziabioside A coupled substituents of cinnamoyl derivatives were designed and synthesized. The synthesized compounds were screened for anticancer activity against a panel of six human cancer cell lines using a MTT assay. Synthetic derivatives showed excellent selectivity, as they were toxic against only HCT116 cell line. Some compounds exhibited better anti-cancer activity against HCT116 compared to positive controls, such as 5-fluorouracil and Albiziabioside A. Compound 8n was the most active derivative. Importantly, it was also found that the anti-proliferative activity of 8n could be attributed to the induction of cell cycle arrest and apoptosis in HCT116 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.