methyl (E)-3-(4-hexyloxy-phenyl)acrylate | 263716-00-3

• 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: methyl (E)-3-(4-hexyloxy-phenyl)acrylate
• 英文别名: methyl (E)-3-(4-hexyloxyphenyl)-2-propenoate；(E)-3-(4-hexyloxy-phenyl)-acrylic acid methyl ester；methyl (E)-3-(4-hexoxyphenyl)prop-2-enoate
• CAS: 263716-00-3
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: WAPWULURGSCWQH-FMIVXFBMSA-N

物化性质

• 熔点：
  77-80 °C(Solv: hexane (110-54-3))
• 沸点：
  382.5±17.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(4-hexyloxy-phenyl)acrylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 Methyl 3-(4-n-hexyloxyphenyl)propionate
  参考文献：
  名称：

  Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes

  摘要：

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.

  DOI：

  10.1021/jm800649q
• 作为产物：
  描述：

  4-正己氧基苯甲醛 、 甲氧羰基亚甲基三苯基正膦 在 氩 、 silica gel 、 ethyl acetate petroleum ether 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以to give 0.244 g (93%) of (E)-3-(4-hexyloxy-phenyl)-acrylic acid methyl ester as a white solid的产率得到methyl (E)-3-(4-hexyloxy-phenyl)acrylate
  参考文献：
  名称：

  PERFLUOROKETONE COMPOUNDS AND USES THEREOF

  摘要：

  本文描述了化学式[I]和[Ia]的新型全氟酮化合物。还描述了它们的用途，例如用于抑制磷脂酶A2活性。还描述了它们的治疗用途，例如用于治疗神经疾病和/或炎症疾病，如脱髓鞘（例如多发性硬化症）和神经损伤（例如脊髓损伤）。

  公开号：

  US20100048727A1

文献信息

• New potent antagonists of leukotrienes C4 and D4. 1. Synthesis and structure-activity relationships
  作者：Hisao Nakai、Mitoshi Konno、Shunji Kosuge、Shigeru Sakuyama、Masaaki Toda、Yoshinobu Arai、Takaaki Obata、Nobuo Katsube、Tsumoru Miyamoto

  DOI：10.1021/jm00396a013

  日期：1988.1

  (p-Amylcinnamoyl)anthranilic acid (3a) had moderate antagonist activities against LTD4-induced smooth muscle contraction on guinea pig ileum and LTC4-induced bronchoconstriction in anesthetized guinea pigs. Modifications were made in the hydrophobic part (cinnamoyl moiety) and the hydrophilic part (anthranilate moiety) of 3a. A series of 8-(benzoylamino)-2-tetrazol-5-yl-1,4-benzodioxans and 8-(ben

  （p-戊基肉桂酰基）邻氨基苯甲酸（3a）对LTD4-诱导的豚鼠回肠平滑肌收缩和LTC4诱导的豚鼠支气管收缩具有中等程度的拮抗活性。对3a的疏水部分（肉桂酰基部分）和亲水部分（邻氨基苯甲酸酯部分）进行了修饰。揭示了一系列的8-（苯甲酰基氨基）-2-四唑-5-基-1，4-苯并二恶烷和8-（苯甲酰基氨基）-2-四唑-5-基-4-氧代-4H-1-苯并吡喃。白三烯C4和D4的有效拮抗剂。在这两个系列中，ONO-RS-347（18k）和ONO-RS-411（19h）分别是最有效和口服活性的拮抗剂。讨论了构效关系。
• Chiral compounds
  申请人：Merck Patent GmbH

  公开号：US06495217B2

  公开（公告）日：2002-12-17

  The invention relates to chiral compounds of formula I wherein R1, R2, X, Y1 and Y2 have the meanings defined herein, as well as to liquid crystalline mixtures comprising at least one chiral compound of formula I. The invention also relates to chiral linear or crosslinked liquid crystalline polymers obtainable by polymerizing a polymerizable mixture comprising at least one chiral compound of formula I, and to the use of chiral compounds of formula I and mixtures and polymers obtained thereof in liquid crystal displays, such as STN, TN, AMD-TN, temperature compensation, guest-host, phase change or surface stabilized or polymer stabilized cholesteric texture (SSCT, PSCT) displays, in active and passive optical elements like polarizers, compensators, alignment layers, color filters or holographic elements in adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, liquid crystal pigments, for decorative and security applications, in nonlinear optics, optical information storage or as chiral dopants, and to a liquid crystal display comprising a mixture comprising at least one chiral compound of formula I.

  该发明涉及式I的手性化合物，其中R1、R2、X、Y1和Y2具有此处定义的含义，以及包含至少一种式I手性化合物的液晶混合物。该发明还涉及通过聚合包含至少一种式I手性化合物的可聚合混合物而可获得的手性线性或交联液晶聚合物，以及在液晶显示器中使用式I手性化合物、混合物和聚合物，例如STN、TN、AMD-TN、温度补偿、客体-宿主、相变或表面稳定或聚合稳定的胆甾醇纹理（SSCT，PSCT）显示器，以及在主动和被动光学元件中，如偏振片、补偿器、取向层、彩色滤光片或全息元件中的使用，还包括在粘合剂、具有各向异性机械性能的合成树脂、化妆品、诊断学、液晶颜料、用于装饰和安全应用、非线性光学、光学信息存储或作为手性掺杂剂，并涉及包含至少一种式I手性化合物的混合物的液晶显示器。
• CHIRAL COMPOUNDS
  申请人：——

  公开号：US20020005505A1

  公开（公告）日：2002-01-17

  The invention relates to chiral compounds of formula I 1 wherein R 1 , R 2 , X, Y 1 and Y 2 have the meanings defined herein, as well as to liquid crystalline mixtures comprising at least one chiral compound of formula I. The invention also relates to chiral linear or crosslinked liquid crystalline polymers obtainable by polymerizing a polymerizable mixture comprising at least one chiral compound of formula I, and to the use of chiral compounds of formula I and mixtures and polymers obtained thereof in liquid crystal displays, such as STN, TN, AMD-TN, temperature compensation, guest-host, phase change or surface stabilized or polymer stabilized cholesteric texture (SSCT, PSCT) displays, in active and passive optical elements like polarizers, compensators, alignment layers, color filters or holographic elements in adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, liquid crystal pigments, for decorative and security applications, in nonlinear optics, optical information storage or as chiral dopants, and to a liquid crystal display comprising a mixture comprising at least one chiral compound of formula I.

  该发明涉及式I1的手性化合物，其中R1，R2，X，Y1和Y2具有所定义的含义，以及至少包含式I的手性化合物的液晶混合物。该发明还涉及通过聚合包含至少一种式I的手性化合物的聚合物可获得手性线性或交联液晶聚合物，以及在液晶显示器（如STN，TN，AMD-TN，温度补偿，客体-主体，相变或表面稳定或聚合稳定胆甾质纹理（SSCT，PSCT）显示器）中使用式I的手性化合物和由此获得的混合物和聚合物，在活性和被动光学元件中，如偏振器、补偿器、定向层、彩色滤光片或全息元件中的粘合剂、具有各向异性机械性能的合成树脂、化妆品、诊断、液晶颜料，用于装饰和安全应用，非线性光学，光学信息存储或作为手性掺杂剂，并涉及包含至少一种式I的手性化合物的混合物的液晶显示器。
• PERFLUOROKETONE COMPOUNDS AND USES THEREOF
  申请人：David Samuel

  公开号：US20100048727A1

  公开（公告）日：2010-02-25

  Novel perfluoroketone compounds of formula [I] and [Ia] are described. Also described are uses thereof, such as for inhibition of phospholipase A 2 activity. Therapeutic uses thereof are also described, such as for the treatment of neural conditions and/or inflammatory conditions, such as demyelinating (e.g., multiple sclerosis) and neural injury (e.g., spinal cord injury).

  本文描述了化学式[I]和[Ia]的新型全氟酮化合物。还描述了它们的用途，例如用于抑制磷脂酶A2活性。还描述了它们的治疗用途，例如用于治疗神经疾病和/或炎症疾病，如脱髓鞘（例如多发性硬化症）和神经损伤（例如脊髓损伤）。
• Non-Chiral Compounds Exhibiting Alternating Tilt Smectic Phases
  作者：R. P. Tuffin、J. W. Goodby、D. Bennemann、G. Heppke、D. Lötzsch、G. Scherowsky

  DOI：10.1080/10587259508038683

  日期：1995.2

  In this article we present an investigation of the liquid crystal properties of nonchiral and racemic branched alkyl chain (swallow-tailed) molecules and some chiral analogues based on a cinnamic acid core group, It was found in these systems that increasing the extent of the branching of the terminal alkyl chain increased the incidence of alternating tilt smectic phases, whereas smectic C-alpha and smectic C-gamma phases were suppressed. X-ray studies of the effect on the layer spacing in the smectic A phase of increasing the long alkyl branch of one series of compounds are included. Results of polarisation studies on some chiral analogues are also reported.