(Z)-(1-iodoethene-1,2-diyl) dibenzene | 156181-20-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-(1-iodoethene-1,2-diyl) dibenzene
• 英文别名: alpha-Iodostilbene；[(Z)-1-iodo-2-phenylethenyl]benzene
• CAS: 156181-20-3
• 化学式: C₁₄H₁₁I
• 分子量: 306.146
• InChiKey: ARCBTFXUWARYBK-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  2
• 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

• 作为反应物：
  描述：

  2,2-联苯基乙酰胺 、 (Z)-(1-iodoethene-1,2-diyl) dibenzene 在 copper(l) iodide 、 caesium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(1,2-Diphenylvinyl)-2,2-diphenylacetamid
  参考文献：
  名称：

  Sequential Copper-Catalyzed Vinylation/Cyclization:  An Efficient Synthesis of Functionalized Oxazoles

  摘要：

  A modular and practical synthesis of highly substituted oxazoles has been developed. The transformation consists of a sequential copper-catalyzed amidation of vinyl halides followed by cyclization promoted by iodine. A wide variety of functionalized oxazoles and polyazoles can be obtained in a selective manner from simple and easily accessible precursors.

  DOI：

  10.1021/ol7024718
• 作为产物：
  描述：

  (E)-(1-iodoethene-1,2-diyl)dibenzene 在 silica gel 、 三碘化磷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (Z)-(1-iodoethene-1,2-diyl) dibenzene
  参考文献：
  名称：

  Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes

  摘要：

  The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes. The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ. Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH2Cl2 solution saturated with HCl, readily afforded the syn addition product, alkenyl chloride (E)-4a. On extended treatment (E)-4a underwent subsequent isomerization to the thermodynamically more stable Z isomer. Thus either isomer of 4a could be obtained in good yield depending on the reaction conditions. In a similar way bromides (E)- and (Z)-4b were obtained without competing formation of the radical products (E)- and (Z)-5, which occurred in solution. In contrast with solution-phase hydriodination of alkyne 1, which slowly afforded iodide (E)-4c, surface-mediated addition readily afforded (E)-4c, followed by isomerization to the Z isomer. E reversible arrow Z equilibration of the alkenyl halides 4 was shown to involve, at least in part, addition-elimination via the gem-dihalides 13. Analogous behavior was exhibited by the phenylalkynes 2 and 3 on surface-mediated hydrohalogenation. Surface-mediated addition of Hbr and HI to the internal alkylalkyne 14 afforded principally the anti addition products (Z)-15b,c. Treatment of the terminal alkynes 17 and 22 with (COBr)(2) over alumina gave the dibromides 20 and 24/25,respectively, whereas use of acetyl bromide as the Hbr precursor afforded the alkenyl bromides 18b and 23.

  DOI：

  10.1021/jo00090a031

文献信息

• Regio- and Stereoselective Hydroiodination of Internal Alkynes with <i>Ex Situ</i>-Generated HI
  作者：Kanako Nozawa-Kumada、Koto Noguchi、Tomoya Akada、Masanori Shigeno、Yoshinori Kondo

  DOI：10.1021/acs.orglett.1c02218

  日期：2021.9.3

  triethylsilane and I2. This system offers high regio- and stereoselectivity to afford (E)-vinyl iodides in good yields under mild conditions. Furthermore, the hydroiodination reaction shows high functional group tolerance toward alkyl, methoxy, halogen, trifluoromethyl, cyano, ester, halomethyl, acid-sensitive silyl ether, and acetal moieties.

  在本文中，我们报道了使用HI内炔的有效且实用的碘氢化生成易地从容易获得的三乙基硅烷和我2。该系统具有高区域选择性和立体选择性，可在温和条件下以良好的收率提供 ( E )-乙烯基碘化物。此外，氢碘化反应显示出对烷基、甲氧基、卤素、三氟甲基、氰基、酯、卤代甲基、酸敏感性甲硅烷基醚和缩醛部分的高官能团耐受性。
• Ruthenium-Catalyzed Regioselective Hydrohalogenation of Alkynes Mediated by Trimethylsilyl Triflate
  作者：Yuye Bai、Zhenyuan Lin、Zhenying Ye、Dian Dong、Jing Wang、Lu Chen、Feng Xie、Yibiao Li、Pierre H. Dixneuf、Min Zhang

  DOI：10.1021/acs.orglett.2c03158

  日期：2022.11.4

  Here we describe a ruthenium-catalyzed regioselective hydrohalogenation reaction of alkynes under mild conditions. Commercially simple halogen sources such as KI, ZnBr2, and ZnCl2 were employed to achieve this transformation. Alkynes derived from bioactive molecules such as l-(−)-borneol, l-menthol, and estrone were also suitable for the transformation, demonstrating the potential synthetic value of

  在这里，我们描述了在温和条件下钌催化的炔烃区域选择性卤化氢反应。采用商业上简单的卤素源，如 KI、ZnBr 2和 ZnCl 2来实现这种转变。来自l -(-)-冰片、l-薄荷醇和雌酮等生物活性分子的炔烃也适用于转化，证明了这种新反应在有机合成中的潜在合成价值。
• HALOCOMBSTATINS AND METHODS OF SYNTHESIS THEREOF
  申请人：Arizona Board Regents, a body corporate of the State of Arizona, acting for and on behalf of Arizona State University

  公开号：EP1802560A2

  公开（公告）日：2007-07-04
• DYNAMIC POLYMER MATERIAL FOR 3D PRINTING
  申请人：INTERNATIONAL BUSINESS MACHINES CORPORATION

  公开号：US20170204292A1

  公开（公告）日：2017-07-20

  A polymer network for 3D printing has a first polymer and a second polymer. The first polymer and the second polymer are crosslinked by a photo-crosslink. The first polymer and the second polymer are independently selected from polylactic acid, poly(acrylonitrile butadiene styrene), polystyrene, nylon, high density polyethylene, polycarbonate, polyvinyl alcohol, polyethylene terephthalate, and thermoplastic polymers.
• US9944826B2
  申请人：——

  公开号：US9944826B2

  公开（公告）日：2018-04-17