(E)-4-butoxycinnamic acid chloride | 77251-77-5

• 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)-4-butoxycinnamic acid chloride
• 英文别名: 4-butoxycinnamoyl chloride；trans-p-butoxycinnamoyl chloride；(E)-3-(4-butoxyphenyl)prop-2-enoyl chloride
• CAS: 77251-77-5
• 化学式: C₁₃H₁₅ClO₂
• 分子量: 238.714
• InChiKey: NGCBCNRYSHJSOH-RMKNXTFCSA-N

物化性质

• 沸点：
  358.1±17.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (E)-4-butoxycinnamic acid chloride 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 30.0h， 生成 2-[2-[(E)-2-(4-butoxyphenyl)ethenyl]-4,5-dihydro-1,3-oxazol-3-ium-3-yl]ethanol;chloride
  参考文献：
  名称：

  肉桂酸衍生的恶唑啉离子作为新型细胞毒性剂。

  摘要：

  取代的肉桂酰氯11被转化为（2-羟乙基）-恶唑啉鎓氯化物14，N，N-双-（2-氯乙基）酰胺16和（2-氯乙基）-恶唑啉鎓氯化物17。尽管衍生物14具有电子-供体取代基（Me或MeO）比被吸电子基团（NO（2），Cl或CF（3））取代的取代基更有效，细胞毒性肌动蛋白的差异不明显。一系列烷氧基取代的衍生物14中亲脂性的修饰导致活性更高的化合物，其中具有4-辛氧基-苯基取代基的14t在microM范围内最有效且显示出细胞毒活性。假定恶唑啉盐起烷基化剂的作用，

  DOI：

  10.1016/s0223-5234(02)01375-2
• 作为产物：
  描述：

  4-丁氧基苯甲醛 生成 (E)-4-butoxycinnamic acid chloride
  参考文献：
  名称：

  Lohar, J. M.; Mahsru, Urvashi, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1981, vol. 20, # 2, p. 125 - 128

  摘要：

  DOI：

文献信息

• Molecular structure and pretilt control of photodimerized-monolayers (PDML)
  作者：Jawad Naciri、Devanand K. Shenoy、Kirsten Grüeneberg、Ranganathan Shashidhar

  DOI：10.1039/b403656e

  日期：——

  We have studied the alignment of nematic liquid crystals on photo-sensitive chemisorbed monolayers. Surface modification and a single UV exposure at normal incidence resulted in photo-dimerized monolayers. A uniform, planar alignment of liquid crystals is realized on these surfaces. Chemical modification of the photo-sensitive chromophores of the monolayer allow fine-tuning of the pretilt. For a given alignment layer, there is a good correlation between the value of the pretilt and the polar properties of the liquid crystal used. Furthermore, the value of the pretilt depends on the chemical functionality at the outermost portion of the photo-alignment layer.

  我们研究了向列型液晶在光敏化学吸附单层上的排列情况。表面修饰和单次垂直紫外曝光导致了光二聚化单层形成。在这种表面上实现了液晶的均匀平面排列。通过化学修饰单层的光敏色团，可以对预倾角进行精细调节。对于给定排列层，预倾角值与所用液晶的极性属性之间存在良好的相关性。此外，预倾角值取决于光对齐层最外层部分的化学功能性。
• Non-thiol Farnesyltransferase Inhibitors: Utilization of the Far Aryl Binding Site by 5-Cinnamoylaminobenzophenones
  作者：Andreas Mitsch、Pia Wißner、Markus Böhm、Katrin Silber、Gerhard Klebe、Isabel Sattler、Martin Schlitzer

  DOI：10.1002/ardp.200400871

  日期：2004.9

  We recently described two novel aryl binding sites of farnesyltransferase. In this study, the cinnamoyl residue was designed as an appropriate substituent for our benzophenone‐based AAX‐peptidomimetic compound capable of occupying the far aryl binding site.

  我们最近描述了法呢基转移酶的两个新的芳基结合位点。在这项研究中，肉桂酰基残基被设计为我们基于二苯甲酮的 AAX 肽模拟化合物的合适取代基，能够占据远芳基结合位点。
• Synthesis and Liquid Crystalline Properties of Novel Ethylene Derivatives
  作者：H. N. Chauhan、R. R. Shah、A. V. Doshi

  DOI：10.1080/15421406.2013.781491

  日期：2013.8

  exhibition of a smectic phase. The transition temperatures of the novel substances were determined by optical polarizing microscopy equipped with a heating stage. A plot of transition temperatures versus the number of carbon atoms present in the n-alkoxy terminal chain represents the phase behavior of the series. An odd-even effect is observed for the nematic-isotropic transition curve. The textures of the

  合成了一系列新型液晶，即α-4-[4'-n-烷氧基肉桂酰氧基]苯甲酰基-β-4″-氯苯基乙烯。该系列由十二个同系物组成。甲基到丁基的衍生物不是液晶，其余的同系物是对映液晶。该系列的辛基至十二烷基衍生物除了具有致线虫的特性外，还具有对映性近晶化，但该系列的戊基、己基、庚基十四烷基和十六烷基同系物仅具有致线虫性，不显示近晶相。新物质的转变温度是通过配备加热台的光学偏光显微镜测定的。转变温度与正烷氧基末端链中存在的碳原子数的关系图代表了该系列的相行为。对于向列-各向同性转变曲线，观察到奇偶效应。向列相的织构为螺纹或纹影型，近晶 A 和近晶 C 相的织构是典型的。分析和光谱数据与分子结构一致。近晶和向列热稳定性分别为 132.6°C 和 156.7°C。近晶相从辛氧基同系物开始。近亲相长度从 26°C 到 33°C 不等，生线虫相长度从 6°C 到 70°C 不等。该系列主要是生线虫，部分是近生的
• Mesomorphic Characteristics of Liquid Crystalline Esters<i>p</i>-Methoxyphenyl<i>p</i>-Alkoxycinnamates
  作者：Jayrang S. Dave、K. P. Dhake

  DOI：10.1246/bcsj.65.559

  日期：1992.2

  The newly synthesized homologous series p-methoxyphenyl p-alkoxycinnamates (I) can be compared with the series N-[p-(p-alkoxycinnamoyloxy)benzylidene] p-anisidines (II).1) All the homologues of both the series (I) and (II) from C1 to C18 are mesogens. In series (II) the first five members decompose due to high transitions at about 300 °C. With decrease in length of the molecules of series (I) than that of series (II), the overall transitions also decrease by about 150 °C. The first seven members in series (II) are nematogens; polymesomorphism begins from octyloxy homologue with the commencement of smectic mesophase and continues to be exhibited upto the last i.e. octadecyloxy homologue. In series (I) also the nematic phase is exhibited upto the heptyl derivative; the smectic phase commences from C8-member in the form of monotropic phase thereby exhibiting polymesomorphism upto the C14 homologue. The last two members of series (II) are smectogens. The odd-even effect is missing in series (II) whereas in series (I), it is seen upto the fifth homologue. In both the series, the N-I curves show a falling tendency— a criterion of high melting series. From textures’ point of view both the series have common features, the nematic phase is threaded when it is the only mesophase shown and homeotropic in polymesomorphic region, whereas the smectic mesophase is focal conic fan shaped of smectic-A variety. This series also yields interesting comparison with the series (III)  p-nitrophenyl p-alkoxycinnamates4) and (IV)  p-chlorophenyl p-alkoxycinnamates.5)

  新合成的同系物系列p-甲氧基苯基p-烷氧基肉桂酸酯（I）可以与系列N-[p-(p-烷氧基肉桂酸酯氧基)苯甲亚胺] p-氨基香豆素（II）进行比较。两系列（I和II）中的所有同系物，从C1到C18都是液晶物质。在系列（II）中，前五个成员因在约300°C时的高转变而分解。由于系列（I）的分子比系列（II）短，整体转变温度也降低了约150°C。系列（II）的前七个成员是向列相物质；多晶相从辛氧同系物开始，伴随形成层状液晶相，并持续到最后一个，即十八烷氧同系物。在系列（I）中，向列相一直展现到庚基衍生物；层状相从C8成员开始，以单调相的形式展现，从而在C14同系物之前显示多晶相。系列（II）的最后两个成员是层状成相物。系列（II）中缺乏奇偶效应，而在系列（I）中，奇偶效应一直存在到第五个同系物。在两个系列中，N-I曲线显示出下降趋势——这是高熔点系列的特征。从纹理的角度来看，这两个系列具有共同特征，当液晶相仅为向列相时呈现出穿-threaded状态，在多晶相区域为同向对称，而层状液晶相则呈现放射状锥形（层状A型）。该系列还与（III）p-硝基苯基p-烷氧基肉桂酸酯和（IV）p-氯苯基p-烷氧基肉桂酸酯进行有趣的比较。
• Structure–activity relationships of novel anti-malarial agents. Part 2: cinnamic acid derivatives
  作者：Jochen Wiesner、Andreas Mitsch、Pia Wißner、Hassan Jomaa、Martin Schlitzer

  DOI：10.1016/s0960-894x(00)00684-3

  日期：2001.2

  We have described compound 1 as a lead structure for a novel class of anti-malarial agents. Replacement of the 3-phenylpropionyl moiety of the lead structure 1 by a 4-propoxycinnamic acid residue resulted in a significant improvement in antimalarial activity. Compound 3q represents an important step in the development of lead structure 1 into an anti-malarial drug candidate. (C) 2001 Elsevier Science Ltd. All rights reserved.