(E)-phenyl 3-phenyl-1-propenyl ether

• 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: (E)-phenyl 3-phenyl-1-propenyl ether
• 英文别名: [(E)-3-phenoxyprop-2-enyl]benzene
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: RVYDGKUROOWEER-NTUHNPAUSA-N

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 (E)-phenyl 3-phenyl-1-propenyl 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

• Palladium(II)-catalyzed phenylation of unsaturated compounds using phenylantimony chlorides under air
  作者：Kazutaka Matoba、Shin-ichi Motofusa、Chan Sik Cho、Kouichi Ohe、Sakae Uemura

  DOI：10.1016/s0022-328x(98)00974-7

  日期：1999.2

  absorption is confirmed in this catalytic reaction and the reaction does not proceed catalytically in palladium(II) under inert gases, such as nitrogen or argon. Even under air the addition of a radical scavenger stopped the reaction. The regeneration of PhPdOAc species from Ph2SbCl, HPdOAc species and oxygen is proposed as a key step in the catalytic cycle where oxygen-containing radical species might

  在室温下，在空气中，在催化量的Pd（OAc）2存在下，二苯基氯化锑和二氯化苯基锑（主要是前者）在室温下与乙腈中的烯烃平稳反应，得到相应的苯基化烯烃（Heck型反应）。与使用三芳基香豆素的类似反应形成鲜明对比的是，该反应不需要添加AgOAc作为再氧化剂。在该催化反应中确认了氧吸收，并且该反应在惰性气体例如氮气或氩气下在钯（II）中没有催化进行。即使在空气中，加入自由基清除剂也会终止反应。从Ph 2再生PhPdOAc物种SbCl，HPdOAc物质和氧被提议作为催化循环中的关键步骤，其中含氧自由基物质可能作为中间体存在。
• Palladium-catalyzed Mizoroki–Heck reaction of allyl aryl ethers with aryl iodides using phosphine-free hydrazone ligands
  作者：Takashi Mino、Hiroaki Shindo、Tomoko Kaneda、Tomoko Koizumi、Yoshio Kasashima、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/j.tetlet.2009.07.046

  日期：2009.9

  Palladium-catalyzed Mizoroki–Heck reaction of allyl aryl ethers with aryl iodides gave aryl cinnamyl ethers using a catalytic amount of Pd(OAc)2 in DMF at 50 °C with phosphine-free hydrazone as a ligand in good yields.

  钯催化的烯丙基芳基醚与芳基碘化物的Mizoroki-Heck反应在50°C下使用催化量的Pd（OAc）2和无膦作为配体，得到芳基肉桂基醚。
• 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。
• An Efficient Palladium-Catalyzed Synthesis of Cinnamyl Ethers from Aromatic Halides, Phenols, and Allylic Chloride
  作者：Wei Wang、Rong Zhou、Zhi-Jie Jiang、Kun Wang、Hai-Yan Fu、Xue-Li Zheng、Hua Chen、Rui-Xiang Li

  DOI：10.1002/adsc.201300757

  日期：2014.2.10

  AbstractA one‐pot, two‐step catalytic protocol for the preparation of cinnamyl ethers from simple and readily available aryl halides, phenols and allyl chloride is reported for the first time. This simple and highly efficient palladium nanoparticles catalytic system shows good regio‐ and stereoselectivities and affords the desired products in good to high yields (49–85%) from aryl iodides. Furthermore, less reactive aryl bromides can also give the cinnamyl ethers in moderate yields (24–72%).magnified image
• US4062862A
  申请人：——

  公开号：US4062862A

  公开（公告）日：1977-12-13