methyl 6-phenyl-2(E)-hexenoate | 55283-02-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 6-phenyl-2(E)-hexenoate
• 英文别名: (E)-6-Phenyl-2-hexensaeuremethylester；methyl (E)-6-phenyl-2-hexenoate；2-Hexenoic acid, 6-phenyl-, methyl ester, (E)-；methyl (E)-6-phenylhex-2-enoate
• CAS: 55283-02-8
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: KZBLVCWGHBYDGQ-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  methyl 6-phenyl-2(E)-hexenoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以98%的产率得到6-苯基己酸甲酯
  参考文献：
  名称：

  Preparation and opioid activity of analogs of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

  摘要：

  A number of analogues of the recently disclosed analgesic dipeptide 2,6-dimethyl-L-tyrosyl-D-alanine-phenylpropylamide (SC-39566,2) were prepared. These analogues contained oxymethylene, aminomethylene, ketomethylene, bismethylene, and trans double bond (including vinyl fluoride) isosteric replacements for the amide bond between the D-alanine and phenylpropylamine units in 2. These compounds were tested in opioid binding assays and in the mouse writhing assay for analgesic activity. Though not as potent as 2, the oxymethylene, and trans double bond isosteres showed analgesic activity. The aminomethylene analogues also showed binding activity in subnanomolar concentrations at the mu-receptor. The amide bond between 2,6-dimethyl-L-tyrosine and D-alanine units seems to be critical for opioid activity.

  DOI：

  10.1021/jm00080a005
• 作为产物：
  描述：

  4-苯基丁醇 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 methyl 6-phenyl-2(E)-hexenoate
  参考文献：
  名称：

  配体控制的钴催化远程硼氢化和烯丙基硅氧烷的烯烃异构化

  摘要：

  烯丙基硅氧烷的共催化远程硼氢化和烯烃异构化是通过配体控制的策略实现的。用 dcype 进行远程硼氢化反应提供硼醚，而 xantphos 有利于形成甲硅烷基烯醇醚。

  DOI：

  10.1039/d1cc05964e

文献信息

• Electrophilic Iron Catalyst Paired with a Lithium Cation Enables Selective Functionalization of Non‐Activated Aliphatic C−H Bonds via Metallocarbene Intermediates
  作者：Alberto Hernán‐Gómez、Mònica Rodríguez、Teodor Parella、Miquel Costas

  DOI：10.1002/anie.201905986

  日期：2019.9.23

  Combining an electrophilic iron complex [Fe(F pda)(THF)]2 (3) [F pda=N,N'-bis(pentafluorophenyl)-o-phenylenediamide] with the pre-activation of α-alkyl-substituted α-diazoesters reagents by LiAl(ORF )4 [ORF =(OC(CF3 )3 ] provides unprecedented access to selective iron-catalyzed intramolecular functionalization of strong alkyl C(sp3 )-H bonds. Reactions occur at 25 °C via α-alkyl-metallocarbene intermediates

  将亲电子配合物[Fe（F pda）（THF）] 2（3）[F pda = N，N'-双（五氟苯基）-邻苯二甲酰胺]与α-烷基取代的α-的预活化结合LiAl（ORF）4 [ORF =（OC（CF3）3]金属碳烯中间体，其活性/选择性与羧酸铑催化剂相似，机理研究表明，锂阳离子在决定亲电性铁碳卡宾中间体的形成速率中起着至关重要的作用，然后通过协同插入CH中进行键。
• Enantioselective hydrolysis of dialkyl 3-monosubstituted glutarates with pig liver esterase: Structure-optical purity relationships
  作者：Masahisa Nakada、Susumu Kobayashi、Masaji Ohno、Shigeo Iwasaki、Shigenobu Okuda

  DOI：10.1016/s0040-4039(00)80391-3

  日期：1988.1

  Dialkyl 3-monosubstituted glutarates are subjected to hydrolysis with pig liver esterase to afford the corresponding chiral half-esters. Synthetically useful half-esters of higher optical purity are obtained from the prochiral substrates of more hydrophobic nature.

  用猪肝酯酶水解3-单取代的戊二酸二烷基酯，得到相应的手性半酯。从具有更疏水性质的前手性底物获得了更高光学纯度的合成上有用的半酯。
• Mass spectrometry in structural and stereochemical problems. CCXV. Behavior of phenyl-substituted .alpha.,.beta.-unsaturated ketones upon electron impact. Promotion of hydrogen rearrangement processes
  作者：R. J. Liedtke、A. F. Gerrard、J. Diekman、Carl Djerassi

  DOI：10.1021/jo00970a025

  日期：1972.3
• Tetrahydronaphthalene Derivatives by Amberlyst® 15-Promoted Friedel-Crafts Cyclizations
  作者：Richard A. Bunce、Andrew N. Cox

  DOI：10.1080/00304940903523553

  日期：2010.2.2
• EISTETTER, K.;WOLF, H. P. O., J. MED. CHEM., 1982, 25, N 2, 109-113
  作者：EISTETTER, K.、WOLF, H. P. O.

  DOI：——

  日期：——