ethyl 3,3,3-triphenylpropionate | 34982-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ethyl 3,3,3-triphenylpropionate
• 英文别名: ethyl 3,3,3-triphenylpropanoate；3,3,3-Triphenyl-propionsaeure-ethylester；Triphenylmethylessigsaeuremethylester；3,3,3-triphenyl-propionic acid ethyl ester；β.β.β-Triphenyl-propionsaeure-aethylester；3,3,3-Triphenyl-propionsaeure-aethylester
• CAS: 34982-21-3
• 化学式: C₂₃H₂₂O₂
• 分子量: 330.426
• InChiKey: ZPVLZVUVYKMVIX-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  447.4±14.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  ethyl 3,3,3-triphenylpropionate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以66%的产率得到3,3,3-triphenylpropan-1-ol
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Cetiedil Analogues as Blockers of the Ca²⁺-Activated K⁺ Permeability of Erythrocytes

  摘要：

  Cetiedil, [2-cyclohexyl-2-(3-thienyl)ethanoic acid 2-(hexahydro-1H-azepin-1-yl)ethyl ester], which blocks the intermediate calcium-activated potassium ion permeability (IKCa) in red blood cells, was used as a lead for investigating structure-activity relationships with the aim of determining the pharmacophore and of synthesizing agents of greater potency. A series of compounds having structures related to cetiedil was made and tested on rabbit erythrocytes. Channel blocking activity within the series was found to correlate well with octanol-water partition coefficients but not with the specific chemical structure of the acid moiety. However, whereas log P for the compounds spans a range of values over 4 orders of magnitude, potency only increases by 2 orders. This suggests that hydrophobic interactions with an active site on the channel are probably not the main determinants of activity. It seems more likely that increased lipophilicity enhances access to the channel, probably from within the cell membrane. In keeping with this interpretation, cetiedil methoiodide was found to be inactive, Triphenylethanoic was found to be a more effective acid grouping than 2-cyclohexyl-2-(3-thienyl)ethanoic, and its 2-(hexahydro-1H-azepin-l-yl)ethyl ester (11) was approximately 3 times more potent than cetiedil. The 9-benzylfluoren-9-yl carboxylic acid ester (21) was found to be approximately 9 times more active than cetiedil, and replacing -CO2- in 21 by an ethynyl (-C dropC-) linkage (compound 26, UCL 1608) increased potency by some 15-fold over that of cetiedil.

  DOI：

  10.1021/jm001113w
• 作为产物：
  描述：

  三苯基氯甲烷 在 硝基苯 作用下， 生成 ethyl 3,3,3-triphenylpropionate
  参考文献：
  名称：

  The Reaction of Ketene with Organic Halogen Compounds¹

  摘要：

  DOI：

  10.1021/ja01202a031

文献信息

• Comparison between Electron Transfer and Nucleophilic Reactivities of Ketene Silyl Acetals with Cationic Electrophiles
  作者：Shunichi Fukuzumi、Kei Ohkubo、Junzo Otera

  DOI：10.1021/jo005733g

  日期：2001.2.1

  d ketene silyl acetal (1: (Me2C=C(OMe)OSiMe3) with trityl cation salt (Ph3C+ClO4-) takes place between 1 and the carbon of para-positon of phenyl group of Ph3C+, whereas a much less sterically hindered ketene silyl acetal (3: H2C=C(OEt)OSiEt3) reacts with Ph3C+ at the central carbon of Ph3C+. The kinetic comparison indicates that the nucleophilic reactivities of ketene silyl acetals are well correlated

  研究了酮甲硅烷基缩醛与一系列对甲氧基取代的三苯甲基阳离子反应的产物和动力学，并将其与由10,10'-二甲基-9,9进行的外球电子转移反应进行了比较。 '，10，10'-四氢-9,9'-二cr啶[（AcrH）2]形成相同系列的三苯甲基阳离子以及其他电子受体。β，β-二甲基取代的烯酮甲硅烷基缩醛（1：（Me2C = C（OMe）OSiMe3）与三苯甲基阳离子盐（Ph3C + ClO4-）的反应中的CC键形成在1和对位碳之间Ph3C +的苯基正位置，而空间位阻少得多的乙烯酮甲硅烷基乙缩醛（3：H2C = C（OEt）OSiEt3）在Ph3C +的中心碳上与Ph3C +反应。
• Holmberg, Acta Academiae Aboensis, Series B: Mathematica et Physica, 1949, vol. 16, # 6, p. 72
  作者：Holmberg

  DOI：——

  日期：——
• Schlenk; Hillemann; Rodloff, Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 135,153
  作者：Schlenk、Hillemann、Rodloff

  DOI：——

  日期：——
• Henderson, Journal of the Chemical Society, 1887, vol. 51, p. 226
  作者：Henderson

  DOI：——

  日期：——
• Hexameric Resorcinarene Capsule is a Brønsted Acid: Investigation and Application to Synthesis and Catalysis
  作者：Qi Zhang、Konrad Tiefenbacher

  DOI：10.1021/ja4080375

  日期：2013.10.30

  Molecular capsules have attracted interest as simple enzyme mimetics and several examples of catalytic transformations in water-soluble metal ligand based systems have been reported. This is not the case for hydrogen-bond based molecular capsules, which in contrast can be employed in organic solvents. We describe herein our investigations of such a system: The resorcin[4]arene hexamer is one of the largest hydrogen bond-based self-assembled capsules and has been studied intensively due to its ready availability. We present evidence that the capsule acts as a reasonably strong Bronsted acid (pK(a) approximately 5.5-6). This finding explains the capsule's high affinity toward tertiary amines that are protonated and therefore encounter cation-pi interactions inside the cavity. We were able to translate this finding into a first synthetic application: A highly substrate-selective Wittig reaction. We also report that this property renders the capsule an efficient enzyme-like catalyst for substrate selective diethyl acetal hydrolysis.