(Z)-1,2-bis(phenylseleno)-ethene | 7392-11-2

• 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: (Z)-1,2-bis(phenylseleno)-ethene
• 英文别名: {[(Z)-2-phenylselenylethenyl]selenyl}benzene；(Z)-1,2-bis(phenylseleno)ethylene；[(Z)-2-phenylselanylethenyl]selanylbenzene
• CAS: 7392-11-2
• 化学式: C₁₄H₁₂Se₂
• 分子量: 338.169
• InChiKey: TVRVZPLVYOVLDT-QXMHVHEDSA-N

物化性质

• 熔点：
  56.5 °C
• 沸点：
  378.9±38.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  sodium phenylselenide 以 六甲基磷酰三胺 为溶剂， 反应 3.0h， 生成 (Z)-1,2-bis(phenylseleno)-ethene
  参考文献：
  名称：

  硒化物阴离子的新合成未活化乙烯基卤化物的亲核取代

  摘要：

  在偶极非质子传递溶剂中，烷基和芳基硒化物阴离子与未活化的乙烯基卤化物反应，以高收率得到烷基或芳基乙烯基硒化物。这些反应是立体特异性的，并且在保留构型的情况下发生。

  DOI：

  10.1016/s0040-4039(01)91274-2

文献信息

• Rhodium-Catalyzed Regio- and Stereoselective 1-Seleno-2-thiolation of 1-Alkynes
  作者：Mieko Arisawa、Yoshihiro Kozuki、Masahiko Yamaguchi

  DOI：10.1021/jo034990t

  日期：2003.11.1

  RhH(PPh(3))(4) and 1,1'-bis(diphenylphosphino)ferrocene catalyze the regio- and stereoselective additions of diaryl disulfides and diaryl diselenides to 1-alkynes giving (Z)-1-arylseleno-2-arylthio-1-alkenes. The catalyst promotes the addition reaction of dibutyl disulfide and dibutyl diselenide to 1-octyne with a similar selectivity giving (Z)-1-butylseleno-2-butylthio-1-octene but with a lower catalytic

  铑配合物RhH（PPh（3））（4）和1,1'-双（二苯基膦基）二茂铁催化二芳基二硫化物和二芳基二硒化物向1-炔烃的区域和立体选择性加成反应，生成（Z）-1-芳基硒代2 -芳硫基-1-烯烃。该催化剂以相似的选择性促进二丁基二硫化物和二丁基二硒化物向1-辛炔的加成反应，得到（Z）-1-丁基硒代-2-丁基硫基-1-辛烯，但催化活性较低。当在RhH（PPh（3））（4）和1,4-二苯基膦基丁烷存在下使用过量的二丁基二硫化物对二丁基二硒化物时，可以更高的产率获得相同的产品。
• Synthesis of unsaturated organochalcogen compounds proceeding from dichloroethenes and organyl dichalcogenides
  作者：E. P. Levanova、V. S. Nikonova、I. B. Rosentsveig、N. V. Russavskaya、A. I. Albanov、N. A. Korchevin

  DOI：10.1134/s107042801708005x

  日期：2017.8

  Reaction of 1,1- and 1,2-dichloroethenes with Ph2S2, Ph2Se2, Bn2S2, and i-Pr2S2 in a system hydrazine hydrate–KOH proceeds as a sequence of successive transformations: dehydrochlorination of initial dichloroethenes to form chloroacetylene, chlorine substitution for the chalcogen-containing nucleophile (ethynylchalcogenides formation), and the addition of the nucleophilic reagent to the triple bond

  1，1-和1,2-二氯乙烯与Ph 2 S 2，Ph 2 Se 2，Bn 2 S 2和i -Pr 2 S 2在水合肼-KOH体系中的反应按连续转化的顺序进行：将最初的二氯乙烯脱氯化氢以形成氯乙炔，用氯取代含硫属元素的亲核试剂（乙炔基硫属元素化物的形成），并将亲核试剂添加到三键中，得到1,2-二卤代乙炔基乙烯。与小灵通的反应-和PHSE -归因于所有阶段的高比率的亲核试剂，获得了主要具有Z构型的1,2-双（苯基硫属酰基）乙烯。在红外条件下，与BnS ‒和i- PrS ‒反应，鉴定了NMR和色谱-质谱图，发现中间的乙炔基硫属元素化物，最终产物由Z异构体盛行的混合物组成。
• Synthesis of vinyl selenides or sulfides and ketene selenoacetals or thioacetals by nickel(II) vinylation of sodium benzeneselenolate or benzenethiolate
  作者：H. J. Cristau、B. Chabaud、R. Labaudiniere、H. Christol

  DOI：10.1021/jo00356a024

  日期：1986.3
• Additions of Organocopper Reagents and Heteroatom Nucleophiles to 1-Phenylseleno-2-(<i>p</i>-toluenesulfonyl)ethyne. Preparation of Vinyl and Allenic Sulfones and Formation of Michael, Anti-Michael, and Rearrangement Products
  作者：Thomas G. Back、Richard J. Bethell、Masood Parvez、Daniel Wehrli

  DOI：10.1021/jo981224r

  日期：1998.10.1

  1-Phenylseleno-2-(p-toluenesulfonyl)ethyne (4) was produced nearly quantitatively from p-(toluenesulfonyl)ethyne and benzeneselenenyl chloride. It underwent stereo- and regioselective syn-additions of organocopper reagents RCu(CN)Li to the beta-position of the sulfone moiety to afford adducts 5. Further reaction of the products with reagents RCu(SePh)Li resulted in substitution of the phenylseleno group with retention of configuration. Control of E,Z-stereochemistry in the product beta,beta-disubstituted vinyl sulfones is therefore achieved by the order of addition of the reagents. Selenoxide syn-elimination of adducts 5 afforded the corresponding allenic sulfones. The additions of amines and alkoxides to 4 produced the corresponding anti-Michael regioisomers (where attack occurred a to the sulfone group) as the major or sole products. The additions were highly stereoselective, proceeding by anti-addition in the anti-Michael series and by syn-addition in the corresponding Michael regioisomers. The reactions of 4 with thiolates and selenolates were more complex, affording rearranged adducts and Michael adducts as the major and minor products, respectively. The formation of the rearranged products can be rationalized by a series of addition-elimination processes. Phenylselenoethyne (43) underwent conjugate additions of pyrrolidine, sodium methoxide, sodium ethanethiolate, and benzeneselenolate anion, affording the corresponding cis isomers via anti-addition. The experiments with heteroatom nucleophiles and acetylenes 4 and 43 show that the phenylseleno group has a surprisingly large activating effect upon conjugate additions.
• Gulliver, David J.; Hope, Eric G.; Levason, William, Journal of the Chemical Society. Perkin transactions II, 1984, # 3, p. 429 - 434
  作者：Gulliver, David J.、Hope, Eric G.、Levason, William、Murray,Stephen G.、Potter, David M.、Marshall, Gregory L.

  DOI：——

  日期：——