1-Benzyl-prop-1-en-1-carbonsaeure | 5707-59-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 1-Benzyl-prop-1-en-1-carbonsaeure
• 英文别名: 2-benzyl-crotonic acid；2-Benzyl-crotonsaeure；α-Benzyl-crotonsaeure；α-Phenyl-β-butylen-β-carbonsaeure；2-benzylbut-2-enoic acid
• CAS: 5707-59-5
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: LUHNRLWMHQQYAM-UHFFFAOYSA-N

物化性质

• 熔点：
  99 °C
• 沸点：
  340.6±21.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-Benzyl-prop-1-en-1-carbonsaeure 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-(2-benzyl-3-mercapto-1-oxobutyl)-L-valinyl-L-tyrosine
  参考文献：
  名称：

  Exploration of neutral endopeptidase active site by a series of new thiol-containing inhibitors

  摘要：

  With the aim of characterizing the active site of the neutral endopeptidase [EC 3.4.24.11 (NEP)] and especially its putative S1 subsite, two series of new thiol inhibitors designed to interact with the S1, S'1, and S'2 subsites of the enzyme have been synthesized. These molecules correspond to the general formula HSCH(R1)CH(R2)CONHCH(R3)COOH (series I) and HSCH(R1)CH(R2)-CONHCH(R3)CONHCH(R4)COOH(series II). Due to the synthetic pathway used, these inhibitors were obtained as mixtures of four stereoisomers. HPLC separation of the stereoisomers of 17 HSCH[CH2CH(CH3)2]CH(CH2Ph)CONHCH(CH3)COOH allowed the stereochemical dependence of the inhibitory potency to be determined. The most active isomer 17b (IC50 = 3.6 nM) is assumed to have the S,S,S stereochemistry as deduced from both NMR and HPLC data. Although none of the inhibitors obtained were significantly more active than thiorphan, HSCH2CH(CH2Ph)-CONHCH2COOH (IC50 = 4 nM), which interacts only with the S'1 and S'2 subsites of NEP, their enhanced hydrophobicity is expected to improve their pharmacokinetic properties. An these compounds displayed low affinities for ACE (IC50s > 1 muM). The determination of the IC50s of two inhibitors of series II for NEP and for a mutated enzyme in which Arg102 was replaced by Glu102 allowed their mode of binding to the active site of NEP to be characterized. The R2 and R3 chains fit the S'1-S'2 subsites, while the R4 group is probably located outside the active site. Taken together these results indicate that the R1 chain of these inhibitors creates no additional stabilizing interactions with the active site of NEP. Two hypotheses may account for this: there is no hydrophobic S1 subsite in NEP or the inhibitors have structures which are too constrained for optimized interactions with the active site.

  DOI：

  10.1021/jm00053a011
• 作为产物：
  描述：

  苄基碘 在 lithium diethylamide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 60.0h， 生成 1-Benzyl-prop-1-en-1-carbonsaeure
  参考文献：
  名称：

  化学合成2-苄基-3-丁烯酸的研究

  摘要：

  化学合成2-苄基-3-丁烯酸3的研究。检查了来自巴豆酸和乙烯基乙酸的二烯酸酯与不同类型的烷基化剂的烷基化。在所有情况下，均获得了异构体3和4的不可分离的混合物。这些混合物的化学选择性酶促酯化以单一产物形式提供酯6，收率为86％，而没有双键异构化。没有一种通用的方法可用于其水解，因为在碱性条件下仅形成异构酸5。为了克服该限制，设计了酶催化的水解过程。该方案以98％的产率提供了异​​构纯的酸3。

  DOI：

  10.1016/j.catcom.2018.05.020

文献信息

• 160. Influence of poles and polar linkings on the course pursued by elimination reactions. Part XXII. Wagner rearrangement in the Hofmann degradation
  作者：Christopher K. Ingold、Maurice A. T. Rogers

  DOI：10.1039/jr9350000722

  日期：——
• Fichter; Alber, Journal fur praktische Chemie (Leipzig 1954), 1906, vol. <2> 74, p. 334
  作者：Fichter、Alber

  DOI：——

  日期：——
• Fichter; Alber, Journal fur praktische Chemie (Leipzig 1954), 1906, vol. <2> 74, p. 335
  作者：Fichter、Alber

  DOI：——

  日期：——
• Vinylogy in Alkylation of t-Butyl Esters
  作者：Keiiti Sisido、Kazuo Sei、Hitosi Nozaki

  DOI：10.1021/jo01054a535

  日期：1962.7
• Fichter; Alber, Journal fur praktische Chemie (Leipzig 1954), 1906, vol. <2>74, p. 336
  作者：Fichter、Alber

  DOI：——

  日期：——