苯基[(E)-3-苯基-2-丙烯基]硒化物 | 69562-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯基[(E)-3-苯基-2-丙烯基]硒化物
• 英文名称: 1-phenyl-3-phenylseleno-1-propene
• 英文别名: phenyl [(E)-3-phenyl-2-propenyl] selenide；(E)-1-Phenyl-3-(phenylseleno)-1-propene；phenyl (E)-3-phenyl-2-propenyl selenide；phenylselenyl-1-phenyl-1-propene；trans-cinnamyl phenyl selenide；(E)-Phenyl cinnamyl selenide；[(E)-3-phenylprop-2-enyl]selanylbenzene
• CAS: 69562-10-3
• 化学式: C₁₅H₁₄Se
• 分子量: 273.236
• InChiKey: DUKPSFGISMJTRF-JXMROGBWSA-N

物化性质

• 熔点：
  61-62 °C
• 沸点：
  377.4±35.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  苯基[(E)-3-苯基-2-丙烯基]硒化物 在 双氧水 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 1-苯基-2-丙烯-1-醇
  参考文献：
  名称：

  Phenylselenodesilylation of allylsilanes and regiospecific transformation of allylsilanes to allylic alcohols via allylselenides

  摘要：

  DOI：

  10.1016/s0040-4039(01)92482-7
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-醇 在 Lindlar's catalyst 吡啶 、 喹啉 、 sodium tetrahydroborate 、 氢气 、 甲基磺酰氯 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 5.0 ℃ 、34.48 kPa 条件下， 反应 18.75h， 生成 苯基[(E)-3-苯基-2-丙烯基]硒化物
  参考文献：
  名称：

  Asymmetric oxidation of simple selenides to selenoxides in high enantiopurity. Stereochemical aspects of the allyl selenoxide/allyl selenenate rearrangement

  摘要：

  For the first time simple alkyl aryl selenoxides of high enantiomeric purity (90-95% ee) and well-defined stereochemistry are available via the asymmetric oxidation of selenides using (+)- or (-)-N-(phenylsulfonyl)-(3,3-dichlorocamphoryl)oxaziridine [4, [3,3-dichloro-1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2,3'-oxaziridine]]]. These nonracemic selenoxides, which are more stable in solution than in the solid state, exhibit high configurational stability as long as acid and moisture are excluded. Complete racemization occurs within minutes on addition of trace amounts of acid and water. The asymmetric oxidation of (E)- and (Z)-aryl cinnamyl selenides 11 and 12 with oxaziridine (+)-4 affords optically active 1-phenyl allyl alcohol (15) via a concerted [2,3] sigmatropic selenoxide-selenenate rearrangement. The extent of 1 --> 3 chirality transfer (41-62% ee) as well as the endo/exo transition state geometry is highly dependent on the structure of the allylic selenide.

  DOI：

  10.1021/jo00035a014

文献信息

• A Facile Method for Synthesis of Alkyl Phenyl Selenides. The Reaction of Diphenyl Diselenide with Oxygen-containing Compounds Using La/Me₃SiCl/^cat.I₂/^cat.CuI System
  作者：Toshiki Nishino、Yutaka Nishiyama、Noboru Sonoda

  DOI：10.1246/cl.2003.918

  日期：2003.10

  Alcohols, ethers, and esters were directly converted to the corresponding alkyl phenyl selenides by the reaction of diphenyl diselenide and the La/Me3SiCl/cat.I2/cat.CuI. It was suggested that alkyl phenyl selenides were formed by the SH2 type reaction of diphenyl diselenide with alkyl radicals generated from alcohols, ethers or esters.

  通过二苯基二硒化物和 La/Me3SiCl/cat.I2/cat.CuI 的反应，醇、醚和酯直接转化为相应的烷基苯基硒化物。有人提出烷基苯基硒化物是由二苯基二硒化物与醇、醚或酯产生的烷基自由基的SH2型反应形成的。
• Hexacarbonylmolybdenum(0)-Induced Dechalcogenization of Allylic Sulfides, Sulfones, and Selenides: Nucleophilic Substitution and Reductive Dechalcogenization
  作者：Yoshiro Masuyama、Kohji Yamada、Soh-hei Shimizu、Yasuhiko Kurusu

  DOI：10.1246/bcsj.62.2913

  日期：1989.9

  Hexacarbonylmolybdenum(0)-induced dechalcogenization of allylic sulfides I, sulfones II, and selenides III in refluxing dioxane, which led to nucleophilic substitutions with carbon nucleophiles. Attack of the relatively bulky nucleophile, 2-ethoxycarbonyl-2-sodiocyclopentanone occurred regioselectively at the less substituted end of the allyl unit after the dechalcogenization to give only one isomer

  六羰基钼 (0) 诱导的烯丙基硫化物 I、砜 II 和硒化物 III 在回流的二恶烷中脱硫，导致碳亲核试剂发生亲核取代。相对庞大的亲核试剂 2-乙氧羰基-2-钠基环戊酮的攻击在脱硫后烯丙基单元的较少取代末端发生区域选择性，仅产生一种异构体。钠丙二酸二乙酯对 I 和 III 的攻击优先发生在 γ 位，而对 II 的攻击优先发生在脱磺酰化后烯丙基单元的更多取代端。在没有碳亲核试剂的情况下，在回流的二恶烷中用 Mo(CO)6 处理​​ I、II 和 III 导致还原性脱硫。H2O 的加入加速了还原脱硫。
• Ionic liquid/PPh3 promoted cleavage of diphenyl disulfide and diselenide: a straight-forward metal-free one-pot route to the synthesis of unsymmetrical sulfides and selenides
  作者：Subhash Banerjee、Laksmikanta Adak、Brindaban C. Ranu

  DOI：10.1016/j.tetlet.2012.02.047

  日期：2012.4

  A metal-free cleavage of diphenyl disulfide and diphenyl diselenide has been achieved using ionic liquid/triphenyl phosphine (PPh3) and a convenient protocol for the one-pot synthesis of unsymmetrical sulfides and selenides by condensing ‘in situ’ generated thiolate or selenate anion with alkyl halides has been developed. In addition, 1,4-conjugate addition of the generated thiolate anions to activated

  使用离子液体/三苯基膦（PPh 3）和便捷的方案，通过“原位”生成的硫醇盐或硒酸根离子缩合一锅合成不对称的硫化物和硒化物，已实现了对二苯基二硫化物和二苯基二硒化物的无金属裂解。已经开发出具有卤代烷的化合物。此外，还证明了将生成的硫醇盐阴离子与1，4-共轭加成到活化烯烃上。离子液体溴化1-甲基-3-戊基咪唑鎓[pmIm] Br在促进反应过程中起着至关重要的作用，并且与其他溶剂相比，具有出色的活性和选择性。[pmIm] Br已被重复使用至少五次而没有明显的活性损失。
• Synthesis of allyl selenides by palladium-catalyzed decarboxylative coupling
  作者：Shelli R. Waetzig、Jon A. Tunge

  DOI：10.1039/b806949b

  日期：——

  This communication details the Pd-catalyzed decarboxylation of selenocarbonates; use of a chiral nonracemic catalyst affords enantioenriched allyl selenides which undergo stereospecific [2,3]-sigmatropic rearrangements to form enantioenriched allylic amines and chlorides.

  该通讯详细介绍了钯催化的硒代碳酸酯的脱羧；手性非外消旋催化剂的使用提供了对映体富集的烯丙基硒化物，其经历了立体有规的[2,3]-σ重排以形成对映体富集的烯丙基胺和氯化物。
• Direct Conversion of a Benzylic Hydroxy Group into a Selenenyl Group Using the Phenyl Trimethylsilyl Selenide-Aluminum Bromide Combination.
  作者：Hitoshi ABE、Akira YAMASAKI、Takashi HARAYAMA

  DOI：10.1248/cpb.46.1311

  日期：——

  A new reagent system, phenyl trimethylsilyl selenide-aluminum bromide, was developed for the direct conversion of various benzylic hydroxy groups into a selenenyl group. Treatment of cinnamyl alcohol with this reagent system yielded 3, 4-dihydro-4-phenyl-2H-1-benzoselenin via a [3, 3]-sigmatropic rearrangement of the intermediate cinnamyl phenyl selenide.

  开发了一种新试剂体系，苯基三甲基甲硅烷基硒化物-溴化铝，用于将各种苄位羟基直接转化为硒烯基。用这种试剂体系处理肉桂醇，通过中间体肉桂基苯基硒化物的[3,3]-σ迁移重排，生成了3,4-二氢-4-苯基-2H-1-苯并硒英。