1-phenylprop-2-enyl phenyl ether | 138621-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-phenylprop-2-enyl phenyl ether
• 英文别名: (R)-1-phenyl-1-phenoxy-2-propene；(R)-1-phenyl-1-phenoxyprop-2-ene；1-phenyl-1-phenoxyprop-2-ene；1-phenoxy-1-phenyl-2-propene；[(1R)-1-phenoxyprop-2-enyl]benzene
• CAS: 138621-80-4
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: MNAOAMBRWJXLQM-OAHLLOKOSA-N

物化性质

• 沸点：
  316.8±11.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-2-丙烯-1-醇 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 chiral biphenyl-2,2'-diyl-phosphoramidite 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 1-phenylprop-2-enyl phenyl ether
  参考文献：
  名称：

  顺序催化异构化和烯丙基取代。外消旋支链烯丙基碳酸酯向对映体富集烯丙基取代产物的转化

  摘要：

  已经开发了一种用于将容易获得的外消旋、支链芳族烯丙酯转化为支链烯丙胺、醚和烷基的催化方案。钯催化的支链烯丙基酯异构化为末端烯丙基酯，然后依次进行铱催化的烯丙基取代，以良好的收率得到支链烯丙基产物，具有高区域异构和对映异构选择性。富电子和缺电子支化烯丙基酯均产生 >90% ee 的产物。对于来自乙酸2-噻吩酯和碳酸二烯酯的反应的产物，也观察到高对映体过量。

  DOI：

  10.1021/ja0644273

文献信息

• Enantio- and regioselective asymmetric allylic substitution using a chiral aminophosphinite ruthenium complex: an experimental and theoretical investigation
  作者：Rajesh K. Jena、Dhiraj Das

  DOI：10.1039/d1ra06824e

  日期：——

  The design and synthesis of a new chiral aminophosphinite-ligated ruthenium complex is described. The ruthenium complex, [Ru(AMP)2(CH3CN)2][BPh4]2 AMP = (S)-tert-butyl 1-(diphenylphosphinooxy)-3-methylbutan-2-ylcarbamate}, has been found to catalyze nucleophilic addition of phenol and carboxylic acid to allyl chloride in a highly regioselective fashion with enantiomeric excess ranging from 12 to 90

  描述了一种新的手性氨基亚膦酸盐配体钌配合物的设计和合成。已发现钌络合物 [Ru(AMP) 2 (CH 3 CN) 2 ][BPh 4 ] 2 AMP = ( S )- tert -butyl 1-(diphenylphosphinooxy)-3-methylbutan-2-ylcarbamate}以高度区域选择性的方式催化苯酚和羧酸与烯丙基氯的亲核加成，对映体过量在 12 至 90 之间。
• Basicity and bulkiness effects of 1,8-diaminonaphthalene, 8-aminoquinoline and their alkylated derivatives on the different efficiencies of η5-C5H5 and η5-C5Me5 ruthenium precatalysts in allylic etherification reactions
  作者：Giovanna Brancatelli、Dario Drommi、Giusy Feminò、Maria Saporita、Giovanni Bottari、Felice Faraone

  DOI：10.1039/c0nj00338g

  日期：——

  The different behaviours of Ru(η5-C5H5) and Ru(η5-C5Me5) precatalysts, [Ru(η5-C5R5)(NCMe)(N,N)]PF6 (R = H, Me), in the allylic etherification reaction of cinnamyl chloride using the phenoxide anion as a nucleophile was considered. The N,N ligands are the commercial products 1,8-diaminonaphthalene and 8-aminoquinoline, and their derivatives obtained by alkylation of the amino nitrogen atoms: alkyl substituents that are also bulky chiral C2-symmetric frameworks allow modulation of the basicity and steric demand of the ligands. Some of the precatalysts, [Ru(η5-C5R5)(NCMe)(N,N)]PF6 (R = H, Me), were also synthesized and characterized. The cinnamyl phenyl ether isomers were obtained with very high B/L regioselectivity values, either with Ru(η5-C5H5) or Ru(η5-C5Me5) precatalysts. The highest B/L regioselectivity values achieved with Ru(η5-C5Me5) precatalysts were found with the N,N ligand 1,8-diaminonaphthalene and its derivatives; with Ru(η5-C5H5) precatalysts best B/L values were obtained with ligands derived from 8-aminoquinoline. A correlation between the B/L regioselectivity, and the σ-donor power and bulkiness of the substituents at the nitrogen atoms of the N,N coordinated ligand was established, but the Ru(η5-C5H5) or Ru(η5-C5Me5) precatalysts followed an opposite trend. It was also found that the low ee values did not depend on the diastereomeric composition of the chiral-at-metal precatalyst [Ru(η5-C5R5)(NCMe)(N,N)]PF6.

  考虑了Ru(η^5-C5H5)和Ru(η^5-C5Me5)前催化剂[Ru(η^5-C5R5)(NCMe)(N,N)]PF6 (R = H, Me)在肉桂氯化物的烯丙醇醚化反应中使用酚氧阴离子作为亲核试剂的不同表现。N,N配体是商业产品1,8-二氨基萘和8-氨基喹啉，以及通过烷基化氨基氮原子获得的其衍生物：也具有大型手性C2对称框架的烷基取代基可以调节配体的碱性和空间需求。一些前催化剂[Ru(η^5-C5R5)(NCMe)(N,N)]PF6 (R = H, Me)也被合成和表征。肉桂酚醚异构体获得了非常高的B/L区域选择性值，无论是使用Ru(η^5- )还是Ru(η^5-C5Me5)前催化剂。与Ru(η^5-C5Me5)前催化剂一起获得的最高B/L区域选择性值是在N,N配体1,8-二氨基萘及其衍生物下找到的；与Ru(η^5- )前催化剂，最佳B/L值是在源自8-氨基喹啉的配体下获得。建立了B/L区域选择性与N,N配体氮原子上取代基的σ-供体能力和体积之间的相关性，但Ru(η^5- )或Ru(η^5-C5Me5)前催化剂则呈现相反的趋势。还发现，低的ee值并不依赖于手性金属前催化剂[Ru(η^5-C5R5)(NCMe)(N,N)]PF6的二对映体组成。
• Development of New P-Chiral Phosphorodiamidite Ligands Having a Pyrrolo[1,2-<i>c</i>]diazaphosphol-1-one Unit and Their Application to Regio- and Enantioselective Iridium-Catalyzed Allylic Etherification
  作者：Masahiro Kimura、Yasuhiro Uozumi

  DOI：10.1021/jo0615403

  日期：2007.2.1

  designed and prepared. They were preliminarily utilized for iridium-catalyzed asymmetric allylic etherification of cinnamyl carbonate with phenol, where both R- and S-products were obtained with good enantioselectivity (up to 74% ee) by changing the N- and P-substituents of the ligands. The opposite enantioselectivity in iridium-catalyzed allylic substitution was explained by DFT calculations of the energy

  设计并制备了十种具有吡咯并[1,2- c ] [1,3,2]二氮杂磷-1-酮骨架的新型P-手性亚磷酰胺基配体。它们被初步用于铱催化的肉桂酸碳酸酯与苯酚的不对称烯丙基烯丙基醚化反应，通过改变配体的N和P取代基，R和S产物均具有良好的对映选择性（最高74％ee）。通过DFT计算π-烯丙基铱-亚磷酰胺基中间体的能量差，可以解释铱催化的烯丙基取代中相反的对映选择性。
• First enantioselective allylic etherification with phenols catalyzed by chiral ruthenium bisoxazoline complexes
  作者：Mbaye D. Mbaye、Jean-Luc Renaud、Bernard Demerseman、Christian Bruneau

  DOI：10.1039/b406039c

  日期：——

  Regio- and enantioselective substitution of cinnamyl chloride by phenols has been achieved with up to 82% enantiomeric excess, using a ruthenium catalyst prepared from [Cp*(CH(3)CN)(3)Ru][PF(6)] and a chiral bisoxazoline ligand.

  使用由[Cp *（CH（3）CN）（3）Ru] [PF（6）]和手性双恶唑啉配体。
• Preparation of chiral ruthenium(iv) complexes and applications in regio- and enantioselective allylation of phenols
  作者：Zeyneb Sahli、Nolwenn Derrien、Simon Pascal、Bernard Demerseman、Thierry Roisnel、Frédéric Barrière、Mathieu Achard、Christian Bruneau

  DOI：10.1039/c0dt01812k

  日期：——

  Facile preparations of chiral [Ru(Cp*)]- and [Ru(Cp′)]-based allyl complexes featuring N,O chelate derived from (+)-nopinone are described. Single crystal X-ray structural analysis of one complex revealed the preferential configuration of the ruthenium centre and the orientation of the unsymmetrical allylic substituent. Applications of these complexes in catalysis for nucleophilic allylic substitution

  描述了基于[Ru（Cp *）]和[Ru（Cp'）]的手性烯丙基复合物的简便制备方法，这些复合物的特征是衍生自（+）-去皮酮的N，O螯合物。一种配合物的单晶X射线结构分析显示了钌中心的优先构型和不对称烯丙基取代基的取向。这些络合物在亲核烯丙基取代的催化中的应用使得可以从苯酚区域和对映选择性地形成支链烯丙基醚。