3-amino-2-(4'-fluorophenyl)propene | 106191-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-amino-2-(4'-fluorophenyl)propene
• 英文别名: β-(4-fluorophenyl)-β-methyleneethanamine；2-(4-fluorophenyl)prop-2-en-1-amine；2-(4-Fluoro-phenyl)-allylamine
• CAS: 106191-62-2
• 化学式: C₉H₁₀FN
• 分子量: 151.184
• InChiKey: XLABCKZIWCCXNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-2-(4'-fluorophenyl)propene 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 2,2'-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-1,1'-binaphthyl 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (R)-5-(bromomethyl)-5-(4-florophenyl)-2-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Enantioselective Bromocyclization of Allylic Amides Catalyzed by BINAP Derivatives

  摘要：

  A highly enantioselective bromocyclization of allylic amides with N-bromosuccinimide (NBS) was developed with DTBM-BINAP as a catalyst, affording chiral oxazolines with a tetrasubstituted carbon center in high yield with up to 99% ee. By utilizing the bromo substituent as a handle, the obtained compounds were converted to synthetically useful chiral building blocks.

  DOI：

  10.1021/acs.orglett.5b00220
• 作为产物：
  描述：

  2-phthalimido-1-(4-fluoro-phenyl)-ethanone 在 sodium hexamethyldisilazane 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 0.5h， 生成 3-amino-2-(4'-fluorophenyl)propene
  参考文献：
  名称：

  不饱和酰胺的催化不对称氯环化

  摘要：

  （DHQD）2 PHAL催化不饱和酰胺的不对称氯环化反应，生成恶唑啉和二氢恶嗪衍生物（参见方案）。该反应操作简单，并使用1-2 mol％的市售（DHQD）2 PHAL（氢奎尼丁1,4-萘二甲酰二醚）催化剂。烯烃以及芳族和脂族烯烃取代基的不同取代方式具有良好的耐受性。DCDPH = N，N-二氯-5,5-二苯基乙内酰脲。

  DOI：

  10.1002/anie.201006910

文献信息

• Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines
  作者：Zhiyang Yan、Bin Sun、Panyi Huang、Haiyun Zhao、Hao Ding、Weike Su、Can Jin

  DOI：10.1016/j.cclet.2021.09.067

  日期：2022.4

  An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions

  开发了一种高效的光催化烯丙基酰胺与N-羟基邻苯二甲酰亚胺酯的烷基化/环化反应。该转化利用烷基自由基攻击烯丙基酰胺，并辅以廉价的玫瑰红作为光催化剂，以中等至优异的产率制备一系列烷基取代的恶唑啉。区域选择性高、操作安全、条件温和、底物通用性好，使该协议具有广阔的应用前景。
• Solvent-Dependent Enantiodivergence in the Chlorocyclization of Unsaturated Carbamates
  作者：Atefeh Garzan、Arvind Jaganathan、Nastaran Salehi Marzijarani、Roozbeh Yousefi、Daniel C. Whitehead、James E. Jackson、Babak Borhan

  DOI：10.1002/chem.201300189

  日期：2013.7.1

  A remarkable solvent‐controlled enantiodivergence is seen in the hydroquinidine 1,4‐phthalazinediyl diether ((DHQD)2PHAL)‐catalyzed chlorocyclization of unsaturated carbamates. Eyring plot analyses of this previously unreported reaction are used to probe and compare the R‐ and S‐selective pathways. In the CHCl3/hexanes solvent system, the pro‐R process shows a surprising increase in selectivity with

  在对苯二酚1,4-酞嗪二基二醚（（DHQD）2 PHAL）催化的不饱和氨基甲酸酯的氯环化反应中，溶剂控制的对映体分布显着。以前未报告的反应的Eyring图分析用于探测和比较R和S选择性途径。在CHCl 3 /己烷溶剂系统中，pro- R过程显示出随温度升高而出乎意料的选择性增加。这些研究指出，亲之间的强烈溶剂依赖性熵焓平衡- [R和亲小号通路。
• Catalytic asymmetric CO₂ utilization reaction for the enantioselective synthesis of chiral 2-oxazolidinones
  作者：Ryuichi Nishiyori、Taiki Mori、Seiji Shirakawa

  DOI：10.1039/d3ob00555k

  日期：——

  asymmetric bromocyclizations of in situ generated carbamic acids from CO2 and allylamines were achieved via the use of a BINOL-derived chiral bifunctional selenide catalyst bearing a hydroxy group. Chiral 2-oxazolidinone products as important pharmaceutical building blocks were obtained with good enantioselectivities by the present catalytic asymmetric CO2 utilization reactions.

  通过使用带有羟基的 BINOL 衍生的手性双功能硒化物催化剂，实现了由 CO 2和烯丙胺原位生成的氨基甲酸的催化不对称溴化环化。通过本催化不对称CO 2利用反应获得了具有良好对映选择性的手性2-恶唑烷酮产物作为重要的药物结构单元。
• Characterization of a Series of 3-Amino-2-phenylpropene Derivatives as Novel Bovine Chromaffin Vesicular Monoamine Transporter Inhibitors
  作者：Rohan P. Perera、D. Shyamali Wimalasena、Kandatege Wimalasena

  DOI：10.1021/jm030004p

  日期：2003.6.1

  A series of 3-amino-2-phenylpropene (APP) derivatives have been synthesized and characterized as novel competitive inhibitors, with K-i values in the muM range, for the bovine chromaffin granule membrane monoamine transporter(s) (bVMAT). Although, these inhibitors are structurally similar to the bVMAT substrate tyramine, none of them were measurably transported into the granule. Structure-activity studies have revealed that, while the 3'- or 4'-OH groups on the aromatic ring enhance the inhibition potency, Me or OMe groups in these positions reduce the inhibition potency. Halogen substitution on the 4'-position of the aromatic ring causes gradual increase of the inhibition potency parallel to the electron donor ability of the halogen. Substituents on the NH2 as well as on the 3-position of the alkyl chain reduce the inhibition potency. Comparative structure-activity analyses of APP derivatives with tyramine and the neurotoxin 1-methyl-4-phenylpyridinium suggest that the flexibility of the side chain and the relative orientation of the NH2 group may be critical for the efficient transport of the substrate through the bVMAT. Comparable bVMAT affinities of these inhibitors to that of DA and other pharmacologically active amines suggest that they are suitable for the structure-activity and mechanistic studies of monoamine transporters and may also be useful in modeling the mechanism of action of amphetamine-related derivatives.
• Stabase-protected 2-chloroallylamine: a useful synthon for primary allylic amines via nickel-catalyzed cross-coupling
  作者：Thomas M. Bargar、Jefferson R. McCowan、James R. McCarthy、Eugene R. Wagner

  DOI：10.1021/jo00380a036

  日期：1987.2