t-amyl cinnamate

• 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: t-amyl cinnamate
• 英文别名: (E)-t-amyl cinnamate；2-methylbutan-2-yl (E)-3-phenylprop-2-enoate
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: GTAAEZZLOYWZDJ-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  肉桂酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 t-amyl cinnamate
  参考文献：
  名称：

  肉桂酸衍生物及其杂芳环类似物作为潜在的高效杀青霉菌的生物活性和结构-活性关系

  摘要：

  合成了一系列肉桂酸衍生物及其杂芳族环类似物，并评价了其对against螨（Psoroptes cuniculi）的体外杀螨活性。其中，有8种化合物显示出更高的活性，中位致死浓度（LC 50）为0.36–1.07 mM（60.4–192.1 µg / mL），并且具有开发新型杀螨剂的巨大潜力。化合物40的最低LC 50值为0.36 mM（60.4 µg / mL），最小中值致死时间（LT 50）在4.5 mM时为2.6 h，与伊维菌素相当[LC 50  = 0.28 mM（247.4 µg / mL） ，LT 50 = 8.9 h]，这是一种杀螨药物标准。SAR分析表明，羰基对活性至关重要。酯部分中烷氧基的类型和链长以及酯基附近的空间位阻显着影响活性。该酯比相应的硫羟酸酯，酰胺，酮或酸更具活性。用α-吡啶基或α-呋喃基取代肉桂酸酯的苯基会显着提高活性。因此，出现了一系列具有优异杀螨活性的肉桂酸酯及其杂芳族环类似物。

  DOI：

  10.1016/j.bmcl.2017.08.051

文献信息

• Reductions of Carboxylic Acids and Esters with NaBH₄ in Diglyme at 162°C
  作者：Hua-Jie Zhu、Charles U. Pittman

  DOI：10.1081/scc-120018935

  日期：2003.1.6

  Aromatic esters, including the extremely sterically hindered ester: t-amyl 2-chlorobenzoate, are readily reduced to the corresponding benzyl alcohols in high yield with NaBH4 in refluxing diglyme (162 degreesC). In sharp contrast, aliphatic esters usually gave only low yields of alcohols. Instead, diglyme fragmentation products are formed which undergo transesterification reactions, producing complex product mixtures including products such as RCOOCH2CH2OCH3. The mechanism of this process involves sodium borohydride-induced S(N)2 cleavage of diglyme (hydride attack) at high temperatures. However, when the extremely electron rich, 3,4,5-trimethoxybenzoic acid is treated with NaBH4/diglyme at 162 degreesC (with or without an equivalent of LiCl), no 3,4,5-trimethyoxybenzyl alcohol is formed. The electron rich and hindered ester, t-amyl-3,4,5-trimethoxybenzoate, also does not reduce under these conditions (with or without LiCl). However, both methyl and isopropyl 3,4,5-trimethoxybenzoate esters were converted into 3,4,5-trimethyoxybenzyl alcohol in good yields in NaBH4/diglyme/LiCl at 162 degreesC. These reductions did not occur unless LiCl was present, illustrating the electron releasing effect of the three methoxy functions which reduce the carbonyl group's reactivity.
• POLARIZING FILM, DISPLAY DEVICE AND PRODUCTION PROCESS THEREOF
  申请人：Morishima Shinichi

  公开号：US20130070899A1

  公开（公告）日：2013-03-21

  A polarizing film comprising a substrate, and a photo alignment film and a light absorption anisotropic film laminated on the substrate in this order, wherein the light absorption anisotropic film has a content ratio of 30% by mass or less of a liquid crystalline non-colorable low molecular weight compound and is obtained by fixing the alignment of a dichroic dye composition comprising at least one nematic liquid crystalline azo dichroic dye; in X-ray diffraction measurement thereof, diffraction peaks derived from periodic structure along a vertical direction to the alignment axis are present, the period indicated by at least one of the diffraction peaks is 3.0 to 15.0A and an intensity of the diffraction peak does not show a maximum value in the range of ±70° of the film normal line direction in a plane vertical to the alignment axis.
• US9382481B2
  申请人：——

  公开号：US9382481B2

  公开（公告）日：2016-07-05
• Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi
  作者：Dong-Dong Chen、Bing-Yu Zhang、Xiu-Xiu Liu、Xing-Qiang Li、Xin-Juan Yang、Le Zhou

  DOI：10.1016/j.bmcl.2017.08.051

  日期：2018.4

  A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 µg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both

  合成了一系列肉桂酸衍生物及其杂芳族环类似物，并评价了其对against螨（Psoroptes cuniculi）的体外杀螨活性。其中，有8种化合物显示出更高的活性，中位致死浓度（LC 50）为0.36–1.07 mM（60.4–192.1 µg / mL），并且具有开发新型杀螨剂的巨大潜力。化合物40的最低LC 50值为0.36 mM（60.4 µg / mL），最小中值致死时间（LT 50）在4.5 mM时为2.6 h，与伊维菌素相当[LC 50  = 0.28 mM（247.4 µg / mL） ，LT 50 = 8.9 h]，这是一种杀螨药物标准。SAR分析表明，羰基对活性至关重要。酯部分中烷氧基的类型和链长以及酯基附近的空间位阻显着影响活性。该酯比相应的硫羟酸酯，酰胺，酮或酸更具活性。用α-吡啶基或α-呋喃基取代肉桂酸酯的苯基会显着提高活性。因此，出现了一系列具有优异杀螨活性的肉桂酸酯及其杂芳族环类似物。