chlorozinc(1+),ethenylbenzene | 119441-92-8

• 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: chlorozinc(1+),ethenylbenzene
• 英文别名: 1-styrenylzinc chloride
• CAS: 119441-92-8
• 化学式: C₈H₇ClZn
• 分子量: 203.987
• InChiKey: DBRMWSKLXGKTGD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  chlorozinc(1+),ethenylbenzene 在 四(三苯基膦)钯 、 bis(η3-allyl-μ-chloropalladium(II)) 2,2'-双(二苯基磷)联苯 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  π-Allylpalladium-Mediated Catalytic Synthesis of Functionalized Allenes

  摘要：

  DOI：

  10.1002/(sici)1521-3773(20000317)39:6<1042::aid-anie1042>3.0.co;2-7
• 作为产物：
  描述：

  alpha- 溴苯乙烯 、 zinc(II) chloride 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 、 四氢呋喃 为溶剂， 反应 1.0h， 生成 chlorozinc(1+),ethenylbenzene
  参考文献：
  名称：

  催化立体选择性硼化反应合成 (+)-Discodermolide

  摘要：

  海洋天然产物 (+)-discodermolide 于 1990 年首次分离出来，至今仍是一个引人注目的合成目标。该化合物不仅具有令人着迷的生物活性，而且还为测试现有化学合成方法提供了机会，并为新反应的开发提供了灵感。 discodermolide 的新合成采用了先前未公开的立体选择性催化二烯硼氢化反应，并且还建立了手性烯醇化物烷基化的策略。此外，discodermolide 的这种合成提供了复杂分子合成中二烯不对称 1,4-二硼化和硼基化二烯-醛偶联的第一个例子。

  DOI：

  10.1002/anie.201405455

文献信息

• (<i>E</i>)-(2-Bromoethenyl)diisopropoxyborane. A New Building Block for (<i>E</i>)-Olefins
  作者：Satoshi Hyuga、Naoko Yamashina、Shoji Hara、Akira Suzuki

  DOI：10.1246/cl.1988.809

  日期：1988.5.5

  (E)-(2-Bromoethenyl)diisopropoxyborane is a useful precursor for the synthesis of (E)-olefins by the stepwise cross-coupling reaction with organozinc chlorides and then with organic halides in the presence of a base, both catalyzed by Pd complex.

  (E)-(2-溴乙烯基)二异丙氧基硼烷是合成(E)-烯烃的有用前体，在钯络合物的催化下，先与有机锌氯化物发生逐步交叉偶联反应，然后在碱存在下与有机卤化物发生反应。
• Synthesis and Transporter Binding Properties of 3β-[4‘-(Phenylalkyl, -phenylalkenyl, and -phenylalkynl)phenyl]tropane-2β-carboxylic Acid Methyl Esters:  Evidence of a Remote Phenyl Binding Domain on the Dopamine Transporter
  作者：Bruce E. Blough、Kathryn I. Keverline、Zhe Nie、Hernán Navarro、Michael J. Kuhar、F. Ivy Carroll

  DOI：10.1021/jm020098n

  日期：2002.8.1

  series of 4'-substituted 3beta-phenyltropane-2beta-carboxylic acid methyl esters were synthesized and evaluated for binding at the dopamine transporter (DAT) in order to better define the pharmacophore for the cocaine binding site on the DAT. Results from the study of 3beta-[(4'-phenylalkyl)phenyl]tropane-2beta-carboxylic acid methyl esters (5a-c and 6a,b) revealed strong evidence of a previously unknown

  合成了一系列4'-取代的3β-苯基托烷-2β-羧酸甲酯，并评估了在多巴胺转运蛋白（DAT）上的结合，以便更好地定义DAT上可卡因结合位点的药效基团。3β-[（（4'-苯基烷基）苯基]托烷-2β-羧酸甲酯（5a-c和6a，b）的研究结果显示了以前未知的远程结合域的有力证据。3beta-[（（4'-苯乙基）苯基] tropane-2beta-羧酸甲酯（5a）在3beta-苯基和远端苯基之间有两个亚甲基接头，其IC（50）值为DAT为5.14 nM。在DAT，3beta- [4'-（苄基）苯基]和3beta- [4'-（苯丙基）苯基]类似物6b和5b的效力分别比5a低102倍和68倍。化合物5a对5-羟色胺和去甲肾上腺素转运蛋白也具有良好的亲和力（分别为K（i）= 21和6.5 nM），因此是非选择性单胺摄取抑制剂。静电效应对3beta-[（4'-苯基烯基）苯基] tropane-2beta-羧
• Computational and Experimental Study on Selective sp²/sp³ or Vinylic/Aryl Carbon–Hydrogen Bond Activation by Platinum(II): Geometries and Relative Stability of Isomeric Cycloplatinated Compounds
  作者：Yumin Li、Jeffrey Carroll、Bradley Simpkins、Deepak Ravindranathan、Christopher M. Boyd、Shouquan Huo

  DOI：10.1021/acs.organomet.5b00326

  日期：2015.7.13

  Cyclometalating ligands 6-(1-phenylethyl)-2,2'-bipyridine (L4), 6-(1-phenylvinyl)-2,2'-bipyridine (LS), and 6-(prop-1-en-2-yl)-2,2'-bipyridine (L6) were synthesized by the Negishi coupling of 6-bromo-2,2'-bipyridine with the corresponding organo-zinc reagents. The reaction of L4 with K2PtCl4 produced only the cycloplatinated compound 4a via sp(2) C-H bond activation. The reactions of L5 and L6 produced exclusively the cycloplatinated compounds 5b and 6a, respectively, via vinylic C-H bond activation. DFT calculations were performed on 12 possible cycloplatination products from the reaction of N-alkyl-N-phenyl-'2,2'-bipyridin-6-amine (alkyl = methyl (L1), ethyl (L2), and isopropyl (L3)) and L4 L6. The results show that compounds 1b-3b resulting from the sp(3) C-H bond activation of L1-L3 are thermodynamic products, and their relative stability is attributed to the planar geometry that allows for a better conjugation. Similar reasoning also applies to the stability of products from vinylic C-H bond activation of L5 and L6. The relative stability of isomeric cycloplatinated compounds 4a and 4b may be due to the different strengths of C-Pt bonds. The steric interaction is the major cause of severe distortion from a planar coordination geometry in the cycloplatinated compounds, which leads to instability of the corresponding cyclometalated products and a higher kinetic barrier for C-H bond activation.
• One-pot conversion of terminal alkynes into gem-disubstituted-alkenes
  作者：Fen-Tair Luo、Shiang-Long Fwu、Wen-Shu Huang

  DOI：10.1016/s0040-4039(00)61789-6

  日期：1992.11

  A one-pot reaction of terminal alkynes with in situ generated hydrogen iodide and organozinc compounds in the presence of Pd(PPh3)4 provided a simple and useful method for the preparation of gem-disubstituted-alkenes.
• Conversion of 2-Iodoaniline into (Z)-3-Methylene-2,3-dihydroindole Derivatives
  作者：Fen-Tair Luo、Ren-Tzong Wang

  DOI：10.3987/com-91-5850

  日期：——

  Treatment of N-(2-iodophenyl)-N-2-propynyl-p-tolylsulfonamide with various organozinc chlorides in the presence of palladium acetate, triphenylphosphine, and 1 equiv. of triethylamine in tetrahydrofuran gives (Z)-3-alkylidene-2,3-dihydroindoles via intramolecular Heck-type reaction and successive cross coupling reactions.