Α,Α-二氰基-2,5-二羟基对苯二乙酸二乙酯 | 57271-90-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: Α,Α-二氰基-2,5-二羟基对苯二乙酸二乙酯
• 英文名称: Hydrochinon-2.5-bis-(α-cyan-essigsaeureethylester)
• 英文别名: 2,2'-dicyano-2,2'-(2,5-dihydroxy-p-phenylene)-di-acetic acid diethyl ester；2.5-Dihydroxy-1.4-bis-(aethoxycarbonyl-cyan-methyl)-benzol；2,2'-Dicyan-2,2'-(2,5-dihydroxy-p-phenylen)-di-essigsaeure-diaethylester；Diethyl 2,2'-(2,5-dihydroxy-1,4-phenylene)bis(cyanoacetate)；ethyl 2-cyano-2-[4-(1-cyano-2-ethoxy-2-oxoethyl)-2,5-dihydroxyphenyl]acetate
• CAS: 57271-90-6
• 化学式: C₁₆H₁₆N₂O₆
• 分子量: 332.313
• InChiKey: BSJNJCUKBYCCQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Α,Α-二氰基-2,5-二羟基对苯二乙酸二乙酯 在 盐酸 、 lithium aluminium tetrahydride 、 氯化亚砜 、 四溴化碳 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 1,4-Bis(bromethyl)-2,5-dimethoxybenzol
  参考文献：
  名称：

  NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation

  摘要：

  Ceramide generation is involved in signal transduction of cellular stress response, in particular during stress-induced apoptosis in response to stimuli such as minimally modified Low-density lipoproteins, TNFalpha and exogenous C-6-ceramide. In this paper we describe 48 diverse synthetic products and evaluate their lysosomotropic and acid sphingomyelinase inhibiting activities in macrophages. A stimuli induced increase of C-16-ceramide in macrophages can be almost completely suppressed by representative compound NB 06 providing an effective protection of macrophages against apoptosis. Compounds like NB 06 thus offer highly interesting fields of application besides prevention of apoptosis of macrophages in atherosclerotic plaques in vessel walls. Most importantly, they can be used for blocking pH dependent lysosomal processes and enzymes in general as well as for analyzing lysosomal dependent cellular signaling. Modulation of gene expression of several prominent inflammatory messengers IL1B, IL6, IL23A, CCL4 and CCL20 further indicate potentially beneficial effects in the field of (systemic) infections involving bacterial endotoxins like LPS or infections with influenza A virus. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.09.021
• 作为产物：
  描述：

  氰乙酸乙酯 、 对苯醌 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 以25%的产率得到Α,Α-二氰基-2,5-二羟基对苯二乙酸二乙酯
  参考文献：
  名称：

  二茂铁-苯并[1,2- b：4,5 - b ']二呋喃-2,6-（3 H，7 H）-二酮加合物的多功能几何异构体：薄膜的二阶非线性光学行为和电荷传输OFET设备†

  摘要：

  合成了一组新的二茂铁-苯并[1,2- b：4,5 - b '] difuran-2,6-（3 H，7 H）-dione dyads的几何异构体，并进行了光学，非线性光学（NLO） ）和电化学性能进行了研究。在少数情况下，通过光谱数据和单晶X射线分析可对化合物进行全面表征。使用飞秒超瑞利散射（HRS）方法在1300 nm下于氯仿中测量二阶非线性极化率。二元组显示出与结构有关的NLO性质，这可以通过与电化学和理论数据的相关性来合理化。的（ž） - 6个生色记录更高β HRS在供体-受体（D-A）型二元体中，其值比相应的（E）-6异构体高。类似地，在d-A-d生色7中，β HRS异构体的值按照顺序（Ž，Ž）>（ê，Ž）>（ê，ê），其与最大吸收波长的趋势以及带隙按此顺序增加的趋势相匹配。由于其固有的结构特征，这些D–A化合物中的两种还被研究为真空沉积的顶部接触底栅薄膜有机场效应晶体管（OFET）

  DOI：

  10.1039/c6tc03876j

文献信息

• The effect of aromatic ring size in electron deficient semiconducting polymers for n-type organic thermoelectrics
  作者：Maryam Alsufyani、Rawad K. Hallani、Suhao Wang、Mingfei Xiao、Xudong Ji、Bryan D. Paulsen、Kai Xu、Helen Bristow、Hu Chen、Xingxing Chen、Henning Sirringhaus、Jonathan Rivnay、Simone Fabiano、Iain McCulloch

  DOI：10.1039/d0tc03347b

  日期：——

  enhance the thermoelectric performance of n-type materials include optimizing the electron affinity (EA) with respect to the dopant to improve the doping process and increasing the charge carrier mobility through enhanced molecular packing. Here, we report the design, synthesis and characterization of fused electron-deficient n-type copolymers incorporating the electron withdrawing lactone unit along the

  N型半导体聚合物近来已用于热电器件中，但是与性能高得多的p型半导体相反，它们通常表现出低电导率和差的器件稳定性。这尤其是由于n型半导体的低掺杂效率和较差的电荷载流子迁移率。增强n型材料热电性能的策略包括针对掺杂剂优化电子亲和力（EA），以改善掺杂过程并通过增强分子堆积来提高电荷载流子迁移率。在这里，我们报告了融合，缺乏电子的n型共聚物的设计，合成和表征结合沿骨架的吸电子内酯单元。使用无金属的醛醇缩合条件合成了聚合物，以探索将中心苯环扩大为萘环对电导率的影响。当n掺杂N-DMBI时，电导率高达0.28 S cm从具有-4.68eV的最大电子亲和力的聚合物中观察到-1的塞贝克系数为-75μVK -1和最大功率因数为0.16μWm -1 K -2。延伸芳环降低了电子亲和力，这是因为降低了吸电子基团的密度，随后电导率降低了近两个数量级。
• Lactone Backbone Density in Rigid Electron‐Deficient Semiconducting Polymers Enabling High n‐type Organic Thermoelectric Performance
  作者：Maryam Alsufyani、Marc‐Antoine Stoeckel、Xingxing Chen、Karl Thorley、Rawad K. Hallani、Yuttapoom Puttisong、Xudong Ji、Dilara Meli、Bryan D. Paulsen、Joseph Strzalka、Khrystyna Regeta、Craig Combe、Hu Chen、Junfu Tian、Jonathan Rivnay、Simone Fabiano、Iain McCulloch

  DOI：10.1002/anie.202113078

  日期：2022.2.7

  Three new n-type semiconducting polymers, P-0, P-50, and P-75 are developed, in which the lactone group densities were maximized by increasing the benzene content from 0 % benzene (P-0), to 50 % (P-50), and 75 % (P-75), to enable co-planar polymers with deep-lying LUMO energy level. As a result, the polymer of P-75 exhibits a good thermoelectric performance with a maximum electrical conductivity of

  开发了三种新型 n 型半导体聚合物 P-0、P-50 和 P-75，其中通过将苯含量从 0% 苯 (P-0) 增加到 50% 来最大化内酯基团的密度（ P-50) 和 75 % (P-75)，以实现具有深层 LUMO 能级的共面聚合物。结果，P-75聚合物表现出良好的热电性能，最大电导率为12 S cm -1，品质因数功率因数为13.2 μWm -1  K -2。
• 2,5-Dihydroxy-p-benzenediacetic Acid and Related Compounds from p-Benzoquinone¹
  作者：J. H. Wood、C. S. Colburn、Lucile Cox、H. C. Garland

  DOI：10.1021/ja01237a038

  日期：1944.9
• Craven, Journal of the Chemical Society, 1931, p. 1605
  作者：Craven

  DOI：——

  日期：——
• NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation
  作者：Markus Blaess、Nelly Bibak、Ralf A. Claus、Matthias Kohl、Gabriel A. Bonaterra、Ralf Kinscherf、Stefan Laufer、Hans-Peter Deigner

  DOI：10.1016/j.ejmech.2017.09.021

  日期：2018.6

  Ceramide generation is involved in signal transduction of cellular stress response, in particular during stress-induced apoptosis in response to stimuli such as minimally modified Low-density lipoproteins, TNFalpha and exogenous C-6-ceramide. In this paper we describe 48 diverse synthetic products and evaluate their lysosomotropic and acid sphingomyelinase inhibiting activities in macrophages. A stimuli induced increase of C-16-ceramide in macrophages can be almost completely suppressed by representative compound NB 06 providing an effective protection of macrophages against apoptosis. Compounds like NB 06 thus offer highly interesting fields of application besides prevention of apoptosis of macrophages in atherosclerotic plaques in vessel walls. Most importantly, they can be used for blocking pH dependent lysosomal processes and enzymes in general as well as for analyzing lysosomal dependent cellular signaling. Modulation of gene expression of several prominent inflammatory messengers IL1B, IL6, IL23A, CCL4 and CCL20 further indicate potentially beneficial effects in the field of (systemic) infections involving bacterial endotoxins like LPS or infections with influenza A virus. (C) 2017 Elsevier Masson SAS. All rights reserved.