methyl 3-(4-(tert-butyl)phenyl)propiolate | 620159-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-(4-(tert-butyl)phenyl)propiolate
• 英文别名: (4-t-Butyl-phenyl)-propynoic acid methyl ester；methyl 3-(4-tert-butylphenyl)prop-2-ynoate
• CAS: 620159-08-2
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: LQXGWENPCGENTO-UHFFFAOYSA-N

物化性质

• 沸点：
  297.8±19.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-(tert-butyl)phenyl)propiolate 在 甲醇 、 水 、 potassium carbonate 作用下， 反应 1.0h， 以95.37%的产率得到3-(4-(tert-butyl)phenyl)propiolic acid
  参考文献：
  名称：

  WO2006/101318

  摘要：

  公开号：
• 作为产物：
  描述：

  对叔丁基苯甲酰氯 以 甲苯 为溶剂， 250.0 ℃ 、133.32 Pa 条件下， 生成 methyl 3-(4-(tert-butyl)phenyl)propiolate
  参考文献：
  名称：

  Pyranone, Thiopyranone, and Pyridone Inhibitors of Phosphatidylinositol 3-Kinase Related Kinases. Structure−Activity Relationships for DNA-Dependent Protein Kinase Inhibition, and Identification of the First Potent and Selective Inhibitor of the Ataxia Telangiectasia Mutated Kinase

  摘要：

  Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholino-pyran-4-ones and 2-morpholino-thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6-(morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.

  DOI：

  10.1021/jm061121y

文献信息

• Palladium-catalyzed cascade carboesterification of norbornene with alkynes
  作者：Wanqing Wu、Can Li、Jianxiao Li、Huanfeng Jiang

  DOI：10.1039/c8ob01799a

  日期：——

  An efficient and convenient palladium-catalyzed cascade carboesterification of norbornenes (NBE) with alkynes has been accomplished to afford functionalized α-methylene γ-lactone and tetrahydrofuran derivatives in good to excellent yields. This new strategy exhibits excellent atom- and step-economy, good functional group tolerance and broad substrate scope. In particular, NBE-palladium species was

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• Recyclable heterogeneous gold(I)-catalyzed oxidation of internal acylalkynes: Practical access to vicinal tricarbonyls
  作者：Wenli Hu、Bin Huang、Bingbo Niu、Mingzhong Cai

  DOI：10.1016/j.tetlet.2021.152953

  日期：2021.3

  A highly efficient heterogeneous gold(I)-catalyzed oxidation of internal acylalkynes has been developed using 2,6-dichloropyridine N-oxide as the oxidant in dichloromethane (CH2Cl2) at room temperature, providing a novel and practical approach for the construction of diverse vicinal tricarbonyls such as α,β-diketoesters, 1,2,3-triketones, and α,β-diketoamides in good to excellent yields. The heterogeneous

  在室温下，使用2,6-二氯吡啶N-氧化物作为二氯甲烷（CH 2 Cl 2）的氧化剂，开发了一种高效的异质金（I）催化内部酰基炔烃氧化的方法，为构建该结构提供了一种新颖而实用的方法种类繁多的邻位三羰基化合物，如α，β-二酮酸酯，1,2,3-三酮和α，β-二酮酰胺，收率良好。可以通过简单的制备方法容易地从市售试剂中获得非均相金（I）催化剂，并通过过滤反应混合物进行回收并重复使用多达七次，而不会显着降低催化效率。
• Efficient Access to Chiral β‐Borylated Carboxylic Esters via Rh‐Catalyzed Hydrogenation
  作者：Gang Liu、Anqi Li、Xueyuan Qin、Zhengyu Han、Xiu‐Qin Dong、Xumu Zhang

  DOI：10.1002/adsc.201900161

  日期：2019.6.18

  Rh/bisphosphine−thiourea ligand (ZhaoPhos)‐catalyzed asymmetric hydrogenation of (Z)‐β‐substituted‐β‐boryl‐α,β‐unsaturated esters was successfully developed, furnishing a variety of chiral β‐borylated carboxylic esters with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). The gram‐scale asymmetric hydrogenation was performed efficiently in the presence of only 0.05 mol%

  成功开发了Rh /双膦-硫脲配体（ZhaoPhos）催化的（Z）-β-取代的-β-硼基-α，β-不饱和酯的不对称加氢反应，提供了高收率的多种手性β-硼化羧酸酯优异的对映选择性（高达99％的收率和> 99％的ee）。在仅0.05 mol％（S / C = 2 000）催化剂负载的情况下，可以有效地进行克级不对称氢化反应，并具有完全转化率，99％的收率和99％的ee。此外，加氢产物很容易转化为其他通用的合成中间体，例如（S）-3-羟基-3-苯基丙酸甲酯和（S）-3-（呋喃-2-基）-3-苯基丙酸甲酯。
• Synthesis of Chiral β-Borylated Carboxylic Esters via Nickel-Catalyzed Asymmetric Hydrogenation
  作者：Zhengyu Han、Gang Liu、Xianghe Zhang、Anqi Li、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1021/acs.orglett.9b00994

  日期：2019.6.7

  The highly efficient Ni-catalyzed asymmetric hydrogenation of β-boronic ester substituted-α,β-unsaturated carboxylic esters was successfully developed using (S,S)-Ph-BPE as the ligand. A series of chiral β-borylated carboxylic esters were obtained with high yields (94%–99% yields) and excellent enantioselectivities (89%–99% ee). The gram-scale asymmetric hydrogenation with a low catalyst loading (0

  以（S，S）-Ph-BPE为配体成功地开发了高效Ni催化的β-硼酸酯取代的α，β-不饱和羧酸酯的不对称加氢反应。获得了一系列高收率（94％–99％收率）和出色的对映选择性（89％–99％ee）的手性β-硼化羧酸酯。具有低催化剂负载量（0.25 mol％）的克级不对称氢化和氢化产物的合成转化证明了该方法的巨大合成效用。
• Organocatalytic <i>trans</i> Phosphinoboration of Internal Alkynes
  作者：Russell G. Fritzemeier、Jan Nekvinda、Christopher M. Vogels、Carol Ann Rosenblum、Carla Slebodnick、Stephen A. Westcott、Webster L. Santos

  DOI：10.1002/anie.202006096

  日期：2020.8.17

  We report the first trans phosphinoboration of internal alkynes. With an organophosphine catalyst, alkynoate esters and the phosphinoboronate Ph2P‐Bpin are efficiently converted into the corresponding trans‐α‐phosphino‐β‐boryl acrylate products in moderate to good yield with high regio‐ and Z‐selectivity. This reaction operates under mild conditions and demonstrates good atom economy, requiring only

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