(2Z,4E)-5-phenylpenta-2,4-dienoic acid | 28010-13-1

• 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: (2Z,4E)-5-phenylpenta-2,4-dienoic acid
• 英文别名: 5-phenylpenta-2(Z),4(E)-dienoic acid；ku-76；1t-phenyl-pentadien-(1.3c)-oic acid-(5)；1t-Phenyl-pentadien-(1.3c)-saeure-(5)；5t-Phenyl-penta-2c,4-diensaeure；cinnamylideneacetic acid
• CAS: 28010-13-1
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: FEIQOMCWGDNMHM-HXGSSHHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• 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

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-5-phenylpenta-2,4-dienoic acid 在 镍 作用下， 生成 5-苯基戊酸
  参考文献：
  名称：

  Roedig,A. et al., Chemische Berichte, 1962, vol. 95, p. 2844 - 2851

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (2Z,4E)-5-phenyl-2,4-pentadienoate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以94%的产率得到(2Z,4E)-5-phenylpenta-2,4-dienoic acid
  参考文献：
  名称：

  Key structural features of cis-cinnamic acid as an allelochemical

  摘要：

  1-O-cis-cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the as-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclo-hexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.08.001

文献信息

• COMPOUND OR ITS TAUTOMER, METAL COMPLEX COMPOUND, COLORED PHOTOSENSITIVE CURING COMPOSITION, COLOR FILTER, AND PRODUCTION
  申请人：MIZUKAWA Yuki

  公开号：US20120238752A1

  公开（公告）日：2012-09-20

  Provided is a colored photosensitive curing composition useful for color filters in primary colors, including blue, green, and red, having a high molar absorption coefficient and allowing a reduction in film thickness and superior color purity and fastness. A colored photosensitive curing composition, comprising, as its colorant, a dipyrromethene-based metal complex compound obtained from a metal or metal compound and a dipyrromethene-based compound represented by the following Formula (I): wherein in Formula (I), R 1 to R 6 each independently represent a hydrogen atom or a substituent group; and R 7 represents a hydrogen or halogen atom, or an alkyl, aryl or heterocyclic group.

  提供的是一种有用于原色彩色滤光片的彩色光敏固化组合物，包括蓝色、绿色和红色，具有高摩尔吸收系数，可减少薄膜厚度，具有优越的颜色纯度和牢固度。 一种彩色光敏固化组合物，包括作为其着色剂的从金属或金属化合物获得的基于二吡咯甲烷的金属配合物化合物和由以下式（I）表示的基于二吡咯甲烷的化合物，其中在式（I）中，R1至R6各自独立地表示氢原子或取代基；R7表示氢或卤素原子，或烷基、芳基或杂环基。
• Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO₂
  作者：Andreu Tortajada、Ryo Ninokata、Ruben Martin

  DOI：10.1021/jacs.7b13220

  日期：2018.2.14

  A site-selective catalytic incorporation of multiple CO2 molecules into 1,3-dienes en route to adipic acids is described. This protocol is characterized by its mild conditions, excellent chemo- and regioselectivity and ease of execution under CO2 (1 atm), including the use of bulk butadiene and/or isoprene feedstocks.

  描述了一种位点选择性催化将多个 CO2 分子结合到 1,3-二烯到己二酸的过程中。该协议的特点是条件温和，具有出色的化学和区域选择性，并且在 CO2 (1 atm) 下易于执行，包括使用散装丁二烯和/或异戊二烯原料。
• Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism
  作者：Mitsuru Shindo、Saki Makigawa、Kenji Matsumoto、Takayuki Iwata、Naoya Wasano、Arihiro Kano、Miyo Terao Morita、Yoshiharu Fujii

  DOI：10.1016/j.phytochem.2020.112287

  日期：2020.4

  bending were determined. The (2E,4E)-, (2Z,4Z)- (2E,4Z)- analogues were inactive, and 4,5-saturated and 4,5-alkynyl analogues also did not show inhibitory activity, demonstrating the importance of the (2Z,4E) diene unit. The aromatic ring was also crucial and could not be replaced with an alkyl chain. Derivatives in which the carboxylic acid was replaced with amides, alcohols, or esters were much less

  此前，我们发现 (2Z,4E)-5-苯基五-2,4-二烯酸 (ku-76) 在 5 μM 浓度下是生菜胚根根向重力弯曲的选择性抑制剂，但没有伴随的生长抑制。在这里，我们描述了 ku-76 的结构-活性关系研究，以确定抑制活性的基本结构特征。合成了一系列 ku-76 类似物，并确定了抑制生菜根向重力弯曲所需的 ku-76 关键特征。 (2E,4E)-、(2Z,4Z)- (2E,4Z)- 类似物无活性，4,5-饱和和 4,5-炔基类似物也不显示抑制活性，这证明了 (2E,4Z)- 类似物的重要性（ 2Z,4E)二烯单元。芳环也很重要，不能用烷基链代替。羧酸被酰胺、醇或酯取代的衍生物的效力要低得多。这些结果表明，(2Z,4E)-二烯、羧酸部分和芳环对于对向重力弯曲的有效抑制活性至关重要。
• Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling
  作者：Lin Huang、Yiting Gu、Alois Fürstner

  DOI：10.1002/asia.201900865

  日期：2019.11.18

  In the presence of simple iron salts, 2-pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6-addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non-thermodynamic Z,E-configured dienoic acid amide derivatives

  在简单的铁盐存在下，2-吡啶酮衍生物在温和的条件下与格氏试剂反应，生成相应的1,6-加成产物。如果在实际添加步骤之后向反应介质中添加了质子惰性的偶极助溶剂，则中间体主要形成屈服开环，从而导致非热力学的Z，E构型的二烯酰胺衍生物，否则很难制备。对照实验以及（三羰基）铁吡啶酮配合物的分离和晶体学表征表明，原位生成的活性铁催化剂对嵌入基质杂环系统中的极化二烯系统表现出高亲和力，这很可能是因为实际识别元素。
• Regio- and Stereoselective Preparation of β,γ-Unsaturated Carboxylic Acids by One-Pot Sequential Double 1,6-Addition of Grignard Reagents to Methyl Coumalate
  作者：Kristína Plevová、Liang Chang、Emmeline Martin、Quentin Llopis、Luc Dechoux、Serge Thorimbert

  DOI：10.1002/adsc.201600212

  日期：2016.10.20

  An efficient regio‐ and stereoselective metal‐catalyzed addition of two Grignard reagents (homo‐coupling, 2 RMgX or hetero‐coupling, R1MgX+R2MgX) to methyl coumalate (methyl 2‐oxo‐2H‐pyran‐5‐carboxylate) is described. This synthetic approach opens the access to a wide variety of functionalized β,γ‐unsaturated carboxylic acids in a modular way. Control of the chemo‐ and stereoselectivity of this one‐pot

  将两种格氏试剂（均偶联，2 RMgX或杂偶联，R 1 MgX + R 2 MgX）有效地在区域和立体选择性金属催化下添加到香豆酸甲酯（甲基2-氧代-2 H-吡喃-5-描述）。这种合成方法以模块化的方式为人们提供了多种功能化的β，γ-不饱和羧酸的途径。讨论了此一锅法化学和立体选择性的控制方法。