硫代苯基溴化镁 | 59384-25-7

• 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: 硫代苯基溴化镁
• 英文名称: thiophenylmagnesium bromide
• 英文别名: Phenylmercaptomagnesiumbromid；Magnesium;benzenethiolate;bromide；magnesium;benzenethiolate;bromide
• CAS: 59384-25-7
• 化学式: C₆H₅BrMgS
• 分子量: 213.381
• InChiKey: UWSDRMIIYHHCDQ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -1.78
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙基二氯硅烷 、 硫代苯基溴化镁 以 乙醚 为溶剂， 反应 1.0h， 以43.4%的产率得到
  参考文献：
  名称：

  Lapkin, I. I.; Novichkova, A. S., Journal of general chemistry of the USSR, 1981, vol. 51, # 2, p. 319 - 321

  摘要：

  DOI：
• 作为产物：
  描述：

  溴苯 在 magnesium 、 sulfur 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 硫代苯基溴化镁
  参考文献：
  名称：

  摘要：

  Reactions of organylchalcogenomagnesium halides RYMgX (in situ) (R = Me, Et, Ph; Y = S, Se, Te; X = Br, I) with (halomethyl)trialkoxysilanes X'CH2Si(OR')(3) X'= Cl, I; R'= Me, Et) at reflux in tetrahydrofuran and the systems of tetrahydrofuran-acetonitrile 1 : 2, and ether-acetonitrile 1 : 2 are studied. These reactions are shown to lead to formation of mixtures of corresponding organyl (trialkoxysilylmethyl)chalcogenide and -dichalcogenide, bis(trialkoxysityl methyl)chalcogenide and -dichalcogenide, as well as the contaminants 2,2,6,6-tetraalkoxy-2,6-disila-4-chalcogen-l-oxane, diorganylchalcogenide and -dichalcogenide, Zn and other organic and organosilicon compounds. Composition of the formed mixtures debends considerably on the structure of R, nature of the chalcogen Y (S, Se, Te), and halides X and X' in the initial reagents, and T reaction conditions. The most of synthesized and isolated organosilicon chalcogenides are newly obtained compounds.

  DOI：

  10.1023/a:1014280007913

文献信息

• Stereospecific synthesis of (E)-vinyl sulphides via 1-lodoalk-1-enyldialkylboranes
  作者：Masayuki Hoshi、Yuzuru Masuda、Akira Arase

  DOI：10.1039/c39850001068

  日期：——

  Isomerically pure (E)-vinyl sulphides were obtained by reaction of 1-iodoalk-1-enylbis(1,2-dimethylpropyl)boranes successively with alkylthiomagnesium bromides, n-butyl-lithium, and aqueous sodium hydroxide.

  通过使1-碘代烷-1-基双（1,2-二甲基丙基）硼烷与烷基硫代溴化镁，正丁基锂和氢氧化钠水溶液依次反应，获得异构纯的（E）-乙烯基硫化物。
• Synthesis and Diels-Alder reactions of 2-alkyl-5-methylene-1,3-dioxolan-4-ones and 2-alkyl-3-acyl-5-methylene-1,3-oxazolidin-4-ones: Highly exo and diastereoface selective chiral ketene equivalents
  作者：William R. Roush、Amy P. Essenfeld、Joseph S. Warmus、Bradley B. Brown

  DOI：10.1016/s0040-4039(00)70683-6

  日期：1989.1

  Chiral dienophiles 1–3 undergo highly exo and diastereoface selective Diels-Alder reactions. The Diels-Alder reactions of 3 are also highly exo selective under Lewis acid catalyzed conditions.

  手性亲双烯体1-3发生高度exo和非对映体选择性Diels-Alder反应。的狄尔斯-阿尔德反应3也路易斯酸催化条件下是高度选择性的外型。
• Julia, Marc; Nel, Maurice; Uguen, Daniel, Bulletin de la Societe Chimique de France, 1987, # 3, p. 487 - 492
  作者：Julia, Marc、Nel, Maurice、Uguen, Daniel

  DOI：——

  日期：——
• Enantioselective synthesis of 2-alkyl-5-methylene-1,3-dioxolan-4-ones and exo-selective Diels-Alder reactions with cyclopentadiene
  作者：William R. Roush、Bradley B. Brown

  DOI：10.1021/jo00038a028

  日期：1992.6

  Highly stereoselective syntheses of chiral dienophiles (R)-1 and (R)-2 are described. Diazotization of L-serine in the presence of HCI and then treatment of the resulting beta-hydroxy-alpha-chloropropionic acid (S)-7 with KOH provides potassium glycidate ((R)-8) in good yield and high enantiomeric purity. Treatment of (R)-8 with PhSH in MeOH then provides alpha-hydroxy acid (S)-10 that can be purified by recrystallization. Condensation of (S)-10 with either pivalaldehyde or cyclohexanecarboxaldehyde followed by oxidation to the sulfone and DBU-promoted elimination of benzenesulfinic acid then provides dienophiles (R)-1 and (R)-2, respectively. Highly exo-selective Diels-Alder reactions of (R)-1 and (R)-2 with cyclopentadiene are also described. The major cycloadduct (-)-15 (94% of total) from the Diels-Alder reaction of 1 was shown to have an enantiomeric purity of greater-than-or-equal-to 99% ee. This figure defines the lower limit of enantiomeric purity of (R)-1. The diastereofacial selectivity of the Diels-Alder reactions of 1 in the exo manifold (50:1) is greater than that of 2 (20:1), as would be expected on the basis of the different steric requirements of the tert-butyl and cyclohexyl substituents of the two reagents. Consequently, dienophile 1 is the preferred reagent for complex synthetic applications, either as a chiral ketene equivalent or in contexts in which the a-hydroxy acid functionality will be preserved in the ultimate synthetic target. Finally, the possible role of dipole effects on the exo selectivity of the Diels-Alder reactions of these and related dienophiles are briefly discussed.
• Synthesis and chemistry of 5,6-dihydropyridinium salt adducts. Synthons for general electrophilic and nucleophilic substitution of the piperidine ring system
  作者：David S. Grierson、Martin Harris、Henri Philippe Husson

  DOI：10.1021/ja00523a026

  日期：1980.1