trans-2-phenyl-1-(4-(trifluoromethyl)phenyl)but-3-en-1-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-2-phenyl-1-(4-(trifluoromethyl)phenyl)but-3-en-1-ol
• 英文别名: (±)-anti-1-(4-trifluoromethylphenyl)-2-phenylbut-3-en-1-ol；(1R,2S)-2-phenyl-1-[4-(trifluoromethyl)phenyl]but-3-en-1-ol
• 化学式: C₁₇H₁₅F₃O
• 分子量: 292.301
• InChiKey: NEHUTBITWQZNGP-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  肉桂基氯 在 1,1'-双(二苯基膦)二茂铁 、 potassium fluoride 、 nickel(II) acetate tetrahydrate 作用下， 以 四氢呋喃 为溶剂， 反应 24.08h， 生成 trans-2-phenyl-1-(4-(trifluoromethyl)phenyl)but-3-en-1-ol
  参考文献：
  名称：

  镍催化醛的烯丙基硼化

  摘要：

  报道了用于醛的烯丙基硼化的镍催化剂，以高非对映选择性促进了均烯丙基醇的制备。观察到的非对映选择性和NMR实验表明，烯丙基化是通过明确定义的六元过渡态发生的，其中镍充当路易斯酸。

  DOI：

  10.1055/s-0039-1690091

文献信息

• Catalytic Nucleophilic Allylation Driven by the Water–Gas Shift Reaction
  作者：Scott E. Denmark、Zachery D. Matesich、Son T. Nguyen、Selena Milicevic Sephton

  DOI：10.1021/acs.joc.7b02658

  日期：2018.1.5

  of this reaction from the initial serendipitous discovery to its general synthetic scope is detailed, highlighting the roles of water, CO, and amine in the generation of a more complete catalytic cycle. The use of unsymmetrical allylic pro-nucleophiles was shown to give preferential product formation through the modulation of reaction conditions. Both (E)-cinnamyl acetate and vinyl oxirane were efficiently

  钌与烯丙基亲核试剂的醛催化烯丙基化已被证明是在温和条件下形成碳-碳键的有效方法。此反应从最初的偶然发现到其一般合成范围的演变过程都进行了详细介绍，突出了水，一氧化碳和胺在更完整的催化循环生成中的作用。结果表明，使用不对称的烯丙基亲核亲核试剂可以通过调节反应条件来优先形成产物。（E）-肉桂酸乙酸酯和乙烯基环氧乙烷均有效地用于形成抗支链产物（抗/ syn最高> 20：1 ）和E-线性产物（最高> 20：1 E / s ）Z）分别与芳香族，α，β-不饱和和脂肪族醛形成高选择性。强调了使反应对映选择性的尝试，包括对苯甲醛高达75:25的对映富集。
• Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction
  作者：Yoshikazu Horino、Ataru Aimono、Naoki Minoshima、Hitoshi Abe

  DOI：10.1016/j.tetlet.2016.06.121

  日期：2016.8

  A palladium-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes was developed. The present protocol provides facile access to synthetically useful (Z)-anti-homoallylic alcohols with high diastereoselectivity and high levels of alkene stereocontrol. Furthermore, single-flask reaction sequences to synthesize (Z)-anti-homoallylic alcohols starting from

  开发了钯催化的3-（频哪醇硼烷基）烯丙基醇，醛和三有机硼烷的三组分反应。本方案提供了容易获得具有高非对映选择性和高水平的烯烃立体控制的合成有用的（Z）-抗同型烯丙基醇的途径。此外，成功地实现了通过使用钯催化的三组分反应从炔丙基醇开始合成（Z）-抗同型烯丙基醇的单烧瓶反应序列。
• Pd-Catalyzed Three-Component Reaction of 3-(Pinacolatoboryl)ally Acetates, Aldehydes, and Organoboranes: A New Entry to Stereoselective Synthesis of (<i>Z</i>)-<i>anti</i>-Homoallylic Alcohols
  作者：Yoshikazu Horino、Ataru Aimono、Hitoshi Abe

  DOI：10.1021/acs.orglett.5b01244

  日期：2015.6.5

  Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl acetates, aldehydes, and organoboranes is described. The reaction is initiated by the formation of an allylic gem-palladium/boryl intermediate, which then undergoes allylation of aldehydes by allylboronates followed by a coupling reaction of in situ generated (Z)-vinylpalladium acetates with organoboranes to provide the (Z)-anti-homoallylic

  描述了Pd催化的3-（频哪醇硼基）烯丙基乙酸酯，醛和有机硼烷的三组分反应。该反应通过形成烯丙基宝石-钯/硼烷基中间体而引发，然后使烯丙基硼酸酯使醛烯丙基化，然后将原位生成的（Z）-乙酸乙烯基钯乙酸酯与有机硼烷偶合，以提供（Z）-抗-非对映选择性高的烯丙基醇和烯烃的立体控制。
• Double Chiral Induction Enables a Stereoselective Carbonyl Allylation with Simple Alkenes under the Sequential Catalysis of Palladium Complex and Chiral Phosphoric Acid
  作者：Lu-Lu Li、Zhong-Lin Tao、Zhi-Yong Han、Liu-Zhu Gong

  DOI：10.1021/acs.orglett.6b03378

  日期：2017.1.6

  An enantioselective carbonyl allylation of aldehydes with simple alkenes has been achieved via a one-pot protocol consisting of a Pd-catalyzed allylic C–H borylation with bis(pinanediolato)diboron and a chiral Brønsted acid catalyzed asymmetric allylborylation, delivering homoallylic alcohols in high yields and with excellent diastereo- and enantioselectivities. The double chiral induction of chiral

  醛与简单烯烃的对映选择性羰基烯丙基化反应是通过一锅法实现的，该方案由Pd催化的烯丙基C–H硼化与双（pin烷二醇基）二硼化反应和手性的Brønsted酸催化的不对称烯丙基化反应，高产率地提供均丁醇并具有出色的非对映和对映选择性。手性烯丙基硼酸酯和手性磷酸的双重手性诱导使反应产生优异的立体选择性。
• Diastereoselective Carbonyl Allylation with Simple Olefins Enabled by Palladium Complex-Catalyzed C–H Oxidative Borylation
  作者：Zhong-Lin Tao、Xing-Han Li、Zhi-Yong Han、Liu-Zhu Gong

  DOI：10.1021/jacs.5b00507

  日期：2015.4.1

  A highly diastereoselective Pd-catalyzed carbonyl allylation of aldehydes and isatins directly using simple acyclic olefins as allylating reagents is described. This transformation is actually a sequential process consisting of a Pd-catalyzed oxidative allylic C-H borylation and an allylboration of carbonyls accelerated by phosphoric acid, wherein a wide scope of olefins could be tolerated. The oxidant is revealed to play a key role in the successful realization of the allylic C-H activation-based allylation.