(2E,5E)-6-phenyl-2,5-hexadien-1-ol | 83413-35-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,5E)-6-phenyl-2,5-hexadien-1-ol
• 英文别名: (2E,5E)-6-phenylhexa-2,5-dien-1-ol；(E,E)-HOCH2CHCHCH2CHCHPh
• CAS: 83413-35-8
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: RQLWSJLTKSXZCP-XJUTULCQSA-N

物化性质

• 沸点：
  87-89 °C(Press: 0.5 Torr)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,5E)-6-phenyl-2,5-hexadien-1-ol 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 四正丁基氢氧化膦 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以71%的产率得到(2S,3S,5E)-2,3-oxirane-6-phenylhex-5-en-1-ol
  参考文献：
  名称：

  Diastereoselective Synthesis of Substituted 2-Phenyltetrahydropyrans as Useful Precursors of Aryl C-Glycosides via Selenoetherification

  摘要：

  The cyclization of several substituted 5-phenyl-pent-4-en-l-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.

  DOI：

  10.3987/com-03-9959
• 作为产物：
  描述：

  (E)-6-phenylhex-5-en-2-yn-1-ol 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以75%的产率得到(2E,5E)-6-phenyl-2,5-hexadien-1-ol
  参考文献：
  名称：

  Diastereoselective Synthesis of Substituted 2-Phenyltetrahydropyrans as Useful Precursors of Aryl C-Glycosides via Selenoetherification

  摘要：

  The cyclization of several substituted 5-phenyl-pent-4-en-l-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.

  DOI：

  10.3987/com-03-9959

文献信息

• Bimetallic η⁶,η¹SCS- and PCP-Pincer Ruthenium Palladium Complexes: Synthesis, Structure, and Catalytic Activity
  作者：Sylvestre Bonnet、Martin Lutz、Anthony L. Spek、Gerard van Koten、Robertus J. M. Klein Gebbink

  DOI：10.1021/om900984t

  日期：2010.3.8

  The synthesis of η6,η1 SCS- and PCP-pincer ruthenium palladium complexes [3]+−[6]+ by direct η6-coordination of [Ru(C5R5)]+ (R = H or Me) to the arene ring of η1-palladated ECE-pincer ligands (E = S or P) is described. In the resulting hetero bis-organometallic complexes, the π- and σ-electrons of the ECE-pincer phenyl anion are involved in η6- and η1-coordination to ruthenium(II) and palladium(II)

  η的合成6，η 1 SCS-和PCP-钳形钌钯络合物[ 3 ] + - [ 6 ] +通过直接η 6的-coordination的[Ru（C 5 - [R 5）] +（R = H或Me）到η的芳烃环1 -palladated ECE-钳配体（E = S或P）进行说明。在所得到的杂双-有机金属络合物中，ECE-钳苯基阴离子的π-和σ-电子参与η 6 - ，η 1-分别与钌（II）和钯（II）配位。除了电化学数据表明两个金属中心都缺乏电子外，还可以通过X射线晶体学和溶液NMR光谱清楚地观察到空间效应。与SCS-钳形衍生物[ 3 ] +和[ 4 ] +，更换新的环戊二烯基的配体（配合物[ 3 ] +）由多种受阻五甲基环戊二烯配体（复合物[ 4 ] +）诱导一个硫原子的构型的反转在固态。平行地，对于[ 3 ] +观察到的硫配体构型的动态转化对于受阻较复杂的复合物[ 4 ] +，溶液中的蛋白质被冷冻
• The Palladium-Catalyzed Cross-Coupling Reaction of Organosilicon Compounds with Allylic Carbonates or Diene Monoxides
  作者：Hayao Matsuhashi、Satoshi Asai、Kazunori Hirabayashi、Yasuo Hatanaka、Atsunori Mori、Tamejiro Hiyama

  DOI：10.1246/bcsj.70.1943

  日期：1997.8

  The cross-coupling reaction of allylic carbonates with organosilanes was found to proceed without fluoride ion activation under mild conditions by using a coordinatively unsaturated palladium complex as a catalyst. The reaction was assumed to proceed through an allylpalladium alkoxide derived from the allylic carbonate substrate and a palladium(0) species, the alkoxo ligand activating the organosilicon

  通过使用配位不饱和钯配合物作为催化剂，发现烯丙基碳酸酯与有机硅烷的交叉偶联反应在温和条件下无需氟离子活化即可进行。假设该反应通过衍生自烯丙基碳酸酯底物的烯丙基钯醇盐和钯 (0) 物质进行，烷氧基配体激活有机硅试剂。同样，一氧化二烯也以中等至高产率与烯基和芳基氟硅烷进行交叉偶联。
• Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes
  作者：Catherine P. McGeough、Alexandra E. Strom、Timothy F. Jamison

  DOI：10.1021/acs.orglett.9b01019

  日期：2019.5.17

  Skipped polyenes featuring high ( E)-selectivity and varying methyl substitution patterns are synthesized using a nickel-catalyzed cross-coupling reaction between allyl trifluoroacetates and vinyl bromides. The utility of this cross-electrophile coupling is showcased in part by the synthesis of the RST fragment of the marine ladder polyether, maitotoxin. Construction of this fragment is particularly

  利用镍催化的三氟乙酸烯丙酯和溴化乙烯之间的交叉偶联反应，合成了具有高（E）选择性和变化的甲基取代模式的跳过的多烯。这种亲电交联的效用部分通过海洋梯形聚醚麦托毒素的RST片段的合成得到了证明。由于交替的甲基取代模式，该片段的构建特别具有挑战性。
• Palladium catalyzed coupling of organostannanes with vinyl epoxides
  作者：David R. Tueting、Antonio M. Echavarren、J.K. Stille

  DOI：10.1016/0040-4020(89)80010-9

  日期：1989.1

  The coupling reaction of organotin reagents with vinyl epoxides, catalyzed by palladium, takes place at ambient temperatures, regioselectively, giving predominately the 1,4-addition product. Both aryl- and vinylstannanes undergo coupling in high yields, while acetylenic, allylic and benzylic tin reagents either give low yields or fail to couple. Although the double bond geometry in the vinylstannane

  钯催化的有机锡试剂与乙烯基环氧化物的偶联反应在环境温度下进行区域选择性的反应，主要产生1,4-加成产物。芳基和乙烯基锡烷均以高收率偶联，而炔属，烯丙基和苄基锡试剂收率较低或无法偶联。尽管在偶联产物中保持了乙烯基锡烷配偶中的双键几何形状，但是来自乙烯基环氧化物的双键几何形状是E / Z混合物。在与环状1，3-二烯单环氧化物的偶联反应中，该反应是立体异构的，有机基团从锡配偶体偶联成反式至醇官能团。
• Palladium-catalyzed cross-coupling reaction of allyl carbonates with organostannanes
  作者：Ana M. Castaño、Antonio M. Echavarren

  DOI：10.1016/0040-4039(96)01406-2

  日期：1996.9

  Allyl carbonates are excellent substrates for the palladium(0)-catalyzed coupling reaction with stannanes under very mild conditions. The reaction proceeds via (η3-allyl)palladium complexes which undergo syn-anti equilibration with a rate similar to that of the transmetallation step.

  在非常温和的条件下，碳酸烯丙酯是钯（0）催化与锡烷偶联反应的优良底物。通过（该反应进行η 3 -烯丙基）合钯络合物经历顺式反平衡用类似于金属转移步骤的速率。