9-蒽丙烯酸 | 5335-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9-蒽丙烯酸
• 英文名称: (E)-3-(anthracen-9-yl)acrylic acid
• 英文别名: 3-(9-anthracenyl)acrylic acid；(E)-9-anthranyl acrylic acid；9-anthraceneacrylic acid；3t-[9]anthryl-acrylic acid；3t-[9]Anthryl-acrylsaeure；3t-(Anthryl-(9))-acrylsaeure；(E)-3-anthracen-9-ylprop-2-enoic acid
• CAS: 5335-33-1
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: VQEMICCPCDGMGE-MDZDMXLPSA-N

物化性质

• 熔点：
  246-247 °C (decomp)
• 沸点：
  487.4±14.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  9-蒽丙烯酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (E)-3-(anthracen-9-yl)acryloyl chloride
  参考文献：
  名称：

  Photoinduced DNA cleavage by anthracene based hydroxamic acids

  摘要：

  Two different series of naphthalene and anthracene based hydroxamic acids having amino acid derivatives were synthesized. Single strand DNA cleavage was achieved on irradiation of newly synthesized hydroxamic acids by UV light (>= 350 nm). Both reactive oxygen species (ROS) and generated radicals from hydroxamic acids were shown to be responsible for the DNA cleavage. Further, DNA cleaving ability of hydroxamic acids was found to be dependent on its concentration and on its structure. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.084
• 作为产物：
  描述：

  (E)-methyl 3-(anthracen-9-yl)acrylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到9-蒽丙烯酸
  参考文献：
  名称：

  N-p-Anisyl-N-methyl-amino-3-(9-anthryl)-propane 的实际合成：一种 Exciplex 荧光“温度计”

  摘要：

  摘要 描述了从 9-蒽醛合成 Np-茴香基-N-甲基-氨基-3-(9-蒽基)-丙烷的实用方法。在这个简单的五步序列中的所有中间体都是结晶的，并且在每个步骤之后简单的重结晶允许在制备规模上制备这种 exciplex 荧光“温度计”分子，而无需借助色谱法。

  DOI：

  10.1080/00397919808005934

文献信息

• Catalytic Hunsdiecker Reaction and One-Pot Catalytic Hunsdiecker–Heck Strategy: Synthesis of α,β-Unsaturated Aromatic Halides, α-(Dihalomethyl)benzenemethanols, 5-Aryl-2,4-pentadienoic acids, Dienoates and Dienamides
  作者：Dinabandhu Naskar、Sujit Roy

  DOI：10.1016/s0040-4020(99)01035-2

  日期：2000.3

  The reaction of α,β-unsaturated aromatic (or heteroaromatic) carboxylic acids with N-halosuccinimides (1 equiv.) and catalytic tetrabutylammonium trifluoroacetate (0.2 equiv.) in dichloroethane results in facile halodecarboxylation affording the corresponding (E)-halides in good to excellent yields. A similar reaction, but with 2 equiv. of N-halosuccinimides in acetonitrile-water (1:1 v/v) results

  α，β-不饱和芳族（或杂芳族）羧酸与N-卤代琥珀酰亚胺（1当量）和催化四丁基三氟乙酸铵（0.2当量）在二氯乙烷中的反应导致容易的卤代羧化，从而得到相应的（E）-卤化物优异的产量。类似的反应，但具有2当量。的N在乙腈-水中（1-1：1 v / v）中的-卤代琥珀酰亚胺导致相应的α-（二卤代甲基）苯甲醇的排他性形成。此外，已开发出一种结合了Hunsdiecker催化反应（在二氯乙烷中使用三氟乙酸四丁基铵）和Heck偶联（使用乙酸钯/三乙胺/三苯基锑/二氯乙烷）的一锅法，用于合成5-芳基-2,4-戊二烯酸，酯和酰胺，产率中等至良好。通过上述途径合成了天然产物胡椒碱和哌瓜胺。机理和理论研究（通过AM1计算）对当前的卤代羧化反应的机理提供了有用的见解，表明离子途径涉及卤离子跨碳-碳双键的攻击，
• Photochemical<i>E</i>(<i>trans</i>)–<i>Z</i>(<i>cis</i>) Isomerization in 9-Anthraceneacrylic Esters
  作者：Majjigapu Janaki Ram Reddy、Uppalanchi Srinivas、Kolupula Srinivas、Vummadi Venkat Reddy、Vaidya Jayathirtha Rao

  DOI：10.1246/bcsj.75.2487

  日期：2002.11

  Several (1–6) 9-anthraceneacrylic esters were synthesized in order to study photochemical E(trans)–Z(cis) isomerization. All of the compounds 1–6 underwent selective E-to-Z isomerization upon direct excitation (> 400 nm) in organic solvents, leading to the formation of a thermodynamically less stable Z isomer over 96%. Triplet sensitized isomerization selectively produces the Z-to-E isomer in over

  为了研究光化学 E(trans)-Z(cis) 异构化，合成了几种 (1-6) 9-蒽丙烯酸酯。在有机溶剂中直接激发（> 400 nm）后，所有化合物 1-6 都经历了选择性 E-to-Z 异构化，导致形成超过 96% 的热力学稳定性较差的 Z 异构体。三重敏化异构化选择性地产生超过 98% 的 Z-to-E 异构体。在三重敏化 Z-to-E 异构化过程中观察到更高的异构化量子产率告诉我们，“量子链”过程正在运行。所有化合物的荧光数据表明 E-to-Z 异构化过程涉及电荷转移或极性单线激发态。
• Chemical reaction method for growing photomechanical organic microcrystals
  作者：Rabih O. Al-Kaysi、Lingyan Zhu、Maram Al-Haidar、Muhannah K. Al-Muhannah、Kheireddine El-Boubbou、Tarafah M. Hamdan、Christopher J. Bardeen

  DOI：10.1039/c4ce02387k

  日期：——

  (E)-3-(Anthracen-9-yl)acrylic acid (9-AYAA) exhibits a strong photomechanical response in bulk crystals but is challenging to grow in microcrystalline form. High quality microcrystals of this molecule could not be grown using techniques like sublimation, reprecipitation, and the floating drop method. If the tertbutyl ester of 9-AYAA is used as a starting material, however, high quality, size-uniform microwires could be grown via acid catalyzed hydrolysis. 9-AYAA microwires with uniform length and thickness were produced after a suspension of (E)-tert-butyl 3-(anthracen-9-yl)acrylate ester microparticles was tumble-mixed in a mixture of phosphoric acid and sodium dodecyl sulfate at 35 °C. The dependence of the results on temperature, surfactant and precursor concentration, and mixing mode was investigated. This chemical reaction-growth method was extended to grow microplates of 9-anthraldehyde using the corresponding acylal as the starting material. Under 475 nm irradiation, the 9-AYAA microwires undergo a photoinduced coiling–uncoiling transition, while the 9-anthraldehyde microplates undergo a folding–unfolding transition.

  (E)-3-(蒽-9-基)丙烯酸（9-AYAA）在块状晶体中表现出强烈的光机械响应，但要生长成微晶形式却很困难。使用升华法、重沉淀法和浮滴法等技术都无法生长出这种分子的高质量微晶。不过，如果使用 9-AYAA 的叔丁酯作为起始材料，则可以通过酸催化水解法培育出高质量、尺寸均匀的微丝。在 35 °C下，将(E)-3-(蒽-9-基)丙烯酸叔丁酯微颗粒悬浮液在磷酸和十二烷基硫酸钠的混合物中翻滚混合，制备出长度和厚度均一的9-AYAA微丝。研究了结果与温度、表面活性剂和前体浓度以及混合方式的关系。这种化学反应生长法扩展到了以相应的酰基醛为起始材料的 9-蒽醛微板生长。在 475 纳米波长的照射下，9-AYAA 微丝经历了光诱导的卷绕-开卷转变，而 9-蒽醛微板则经历了折叠-开折转变。
• THE WILLGERODT REACTION. V. SUBSTITUTED ACETAMIDES FROM β-SUBSTITUTED ACRYLIC ACIDS¹
  作者：COLLIS H. DAVIS、MARVIN CARMACK

  DOI：10.1021/jo01165a010

  日期：1947.1
• Is metal necessary in the Hunsdiecker-Borodin reaction?
  作者：Dinabandhu Naskar、Shantanu Chowdhury、Sujit Roy

  DOI：10.1016/s0040-4039(97)10639-6

  日期：1998.2

  The tetrabutylammonium trifluoroacetate (TBATFA) catalyzed conversion of alpha,beta-unsaturated carboxylic acids to the corresponding halides with N-halosuccinimides in dichloroethane is reported as the first example of a metal-free catalytic version of the title reaction The methodology was further employed for a facile synthesis of piperine. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.