(E)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-ol | 39274-70-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-ol
• CAS: 39274-70-9
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: CAYYISAFUATPKQ-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-ol 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二异丙酯 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 异辛烷 为溶剂， 反应 4.83h， 以98% ee的产率得到
  参考文献：
  名称：

  N-氟烯基三氟甲基亚胺的区域和对映体选择性钯催化的不对称烯丙基化。

  摘要：

  公开了N-芴基三氟甲基亚胺与烯丙基乙酸酯的钯催化的不对称烯丙基化。该方法提供了可扩展且有效的途径，以高收率获得具有两个相邻的立体中心和一个烯丙基的多取代的手性α-三氟甲基胺，具有极好的区域，非对映异构和对映选择性。重要的是，该方法还为区域异构产物的合成提供了强有力的策略，并且区域选择性由手性催化剂和光学活性底物控制。

  DOI：

  10.1021/acs.orglett.0c01836
• 作为产物：
  描述：

  (2E)-1-(4-硝基苯基)-3-苯基-2-丙烯-1-酮 在 sodium tetrahydroborate 作用下， 生成 (E)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-ol
  参考文献：
  名称：

  Efficient chemoselective biohydrogenation of 1,3-diaryl-2-propen-1-ones catalyzed by Saccharomyces cerevisiae yeasts in biphasic system

  摘要：

  A series of chalcones (1-9) was synthesized by base catalyzed aldol condensation with 50-94% yields. These alpha,beta-unsaturated carbonyl compounds were used as substrates in biotransformation reactions mediated by three industrial Saccharomyces cerevisiae strains in biphasic systems. Several reaction parameters were evaluated, such as yeast concentration, temperature, pH, substrate concentration, organic solvent, volume of aqueous and organic phases and the influence of substituent groups on chalcones 1-9. The biotransformation was chemoselective and formed only the corresponding saturated ketones. The highest conversion (>99%) to the dihydrochalcone was obtained at 30-45 degrees C and pH above 5.5, while the cellular and substrate concentrations also showed a strong influence on the biohydrogenation reaction. Organic solvents with log P >3.2 (hexane or heptane) were the most appropriate, and 40-80% of aqueous phase allowed the highest conversions probably by maintaining the yeast enzymes catalytically active. The influence of substituents on rings A and B of chalcones 1-9 was low and no correlation between the donor or withdrawing electron groups was observed. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.01.010

文献信息

• Direct azidation of allylic/benzylic alcohols and ethers followed by the click reaction: one-pot synthesis of 1,2,3-triazoles and 1,2,3-triazole moiety embedded macrocycles
  作者：Naveen、Srinivasarao Arulananda Babu、Nayyar Ahmad Aslam、Akshey Sandhu、Dharmendra Kumar Singh、Ameet Rana

  DOI：10.1016/j.tet.2015.06.099

  日期：2015.9

  of allylic/benzylic alcohols or their methyl ethers followed by the click reaction are reported. Two methods involving sequential reactions were developed for synthesizing substituted 1,2,3-triazoles starting from allylic/benzylic alcohols. The first method involves magnetically separable nano Fe3O4-catalyzed direct azidation of various allylic/benzylic alcohols with TMSN3 as the first step followed

  报道了对烯丙基/苄基醇或其甲基醚的一锅直接叠氮化并随后进行点击反应的研究。开发了两种涉及顺序反应的方法，用于从烯丙基/苄基醇开始合成取代的1,2,3-三唑。第一种方法涉及第一步，以TMSN 3进行磁性可分离的纳米Fe 3 O 4催化的各种烯丙基/苄基醇的直接叠氮化，然后第二步进行叠氮化物与炔烃的Cu催化点击反应。第二种方法涉及Cu（OTf）2催化烯丙基/苄醇及其甲基醚与TMSN 3的直接叠氮化。第一步，然后进行叠氮化物与炔烃的点击反应，作为第二步。在该方法中，Cu（OTf）2用作酒精叠氮化和点击反应步骤的单一催化剂。通过合成嵌入1,2,3-三唑和1,3-二炔单元的新型聚醚系统和大分子化合物，已揭示了该方案的实用性。
• Rhodium-catalyzed Addition of Aryl- and Alkenylsilanediols to Aldehydes
  作者：Toshinari Fujii、Tooru Koike、Atsunori Mori、Kohtaro Osakada

  DOI：10.1055/s-2002-19786

  日期：——

  Arylation and alkenylation of aromatic aldehydes with silanediols is shown to proceed by use of a catalytic amount of rhodium complex. Treatment of ethyl(4-methoxyphenyl)silanediol with benzaldehyde in the presence of 3 mol% of [Rh(OH)(cod)]2 affords 4-methoxyphenyl(phenyl)methanol in 59% yield after stirring at 70 °C for 24 hours. On the other hand, diarylketone was also obtained at elevated temperature via β-hydride elimination from intermediary rhodium alkoxide.

  芳香醛与硅烷二醇的芳基化和烯基化反应是通过使用催化量的铑络合物进行的。在 3 mol% 的 [Rh(OH)(cod)]2 存在下用苯甲醛处理乙基(4-甲氧基苯基)硅烷二醇，在 70 °C 搅拌 24 小时后得到 4-甲氧基苯基(苯基)甲醇，收率 59% 。另一方面，二芳基酮也是在高温下通过中间醇铑消除β-氢化物而获得的。
• Potassium Alkenyl- and Aryltrifluoroborates:  Stable and Efficient Agents for Rhodium-Catalyzed Addition to Aldehydes and Enones
  作者：Robert A. Batey、Avinash N. Thadani、David V. Smil

  DOI：10.1021/ol9910767

  日期：1999.11.1

  [GRAPHICS]Potassium alkenyl- and aryltrifluoroborates undergo addition to enones and aldehydes in the presence of Rh(1) catalysts to give beta-functionalized ketones and allylic/benzylic alcohols, respectively. Reaction proceeds more rapidly than with the corresponding boronic acids, and the choice of phosphine ligand does not signifcantly influence the overall efficiency of addition.
• Efficient chemoselective biohydrogenation of 1,3-diaryl-2-propen-1-ones catalyzed by Saccharomyces cerevisiae yeasts in biphasic system
  作者：Vanessa Dutra Silva、Boris Ugarte Stambuk、Maria da Graça Nascimento

  DOI：10.1016/j.molcatb.2010.01.010

  日期：2010.5

  A series of chalcones (1-9) was synthesized by base catalyzed aldol condensation with 50-94% yields. These alpha,beta-unsaturated carbonyl compounds were used as substrates in biotransformation reactions mediated by three industrial Saccharomyces cerevisiae strains in biphasic systems. Several reaction parameters were evaluated, such as yeast concentration, temperature, pH, substrate concentration, organic solvent, volume of aqueous and organic phases and the influence of substituent groups on chalcones 1-9. The biotransformation was chemoselective and formed only the corresponding saturated ketones. The highest conversion (>99%) to the dihydrochalcone was obtained at 30-45 degrees C and pH above 5.5, while the cellular and substrate concentrations also showed a strong influence on the biohydrogenation reaction. Organic solvents with log P >3.2 (hexane or heptane) were the most appropriate, and 40-80% of aqueous phase allowed the highest conversions probably by maintaining the yeast enzymes catalytically active. The influence of substituents on rings A and B of chalcones 1-9 was low and no correlation between the donor or withdrawing electron groups was observed. (C) 2010 Elsevier B.V. All rights reserved.
• Regio- and Enantioselective Palladium-Catalyzed Asymmetric Allylation of <i>N</i>-Fluorenyl Trifluoromethyl Imine
  作者：Wei Wang、Qin Xiong、Liang Gong、Yingwei Wang、Jie Liu、Yu Lan、Xia Zhang

  DOI：10.1021/acs.orglett.0c01836

  日期：2020.7.17

  and efficient access to polysubstituted chiral α-trifluoromethyl amines bearing two adjacent stereocenters and one allyl group in high yields with excellent regio-, diastereo-, and enantioselectivity. Importantly, this method also provides a powerful strategy for the synthesis of both regioisomeric products and the regioselectivity is controlled by the chiral catalysts and optically active substrates

  公开了N-芴基三氟甲基亚胺与烯丙基乙酸酯的钯催化的不对称烯丙基化。该方法提供了可扩展且有效的途径，以高收率获得具有两个相邻的立体中心和一个烯丙基的多取代的手性α-三氟甲基胺，具有极好的区域，非对映异构和对映选择性。重要的是，该方法还为区域异构产物的合成提供了强有力的策略，并且区域选择性由手性催化剂和光学活性底物控制。