(Z)-1-iodo-2-phenyl-1-(trimethylsilyl)ethene | 101653-70-7

• 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-iodo-2-phenyl-1-(trimethylsilyl)ethene
• 英文别名: (Z)-1-iodo-1-trimethylsilyl-2-phenylethene；(1-iodo-2-phenylvinyl)trimethylsilane；[(Z)-1-iodo-2-phenylethenyl]-trimethylsilane
• CAS: 101653-70-7
• 化学式: C₁₁H₁₅ISi
• 分子量: 302.23
• InChiKey: CNVINQGJURKHOI-PKNBQFBNSA-N

物化性质

• 沸点：
  86-90 °C(Press: 0.3 Torr)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (Z)-1-iodo-2-phenyl-1-(trimethylsilyl)ethene 在 sodium hydroxide 、 正丁基锂 作用下， 反应 45.25h， 生成 3,3-二苯基丙酸
  参考文献：
  名称：

  Conjugate addition reactions of .alpha.-silylated .alpha.,.beta.-unsaturated carboxylic acid salts

  摘要：

  DOI：

  10.1021/jo00235a016
• 作为产物：
  描述：

  styryltrimethylsilane 在 碘 、 Diisobutylalan 作用下， 生成 (Z)-1-iodo-2-phenyl-1-(trimethylsilyl)ethene
  参考文献：
  名称：

  Conjugate addition reactions of .alpha.-silylated .alpha.,.beta.-unsaturated carboxylic acid salts

  摘要：

  DOI：

  10.1021/jo00235a016

文献信息

• Palladium-Catalyzed Regio- and Stereoselective Synthesis of (<i>E</i>)-1,3-Bissilyl-6-arylfulvenes from Aryl Iodides and Silylacetylenes
  作者：Souta Suzuki、Hidenori Kinoshita、Katsukiyo Miura

  DOI：10.1021/acs.orglett.9b00144

  日期：2019.3.15

  3-bissilyl-6-arylfulvenes has been developed. The reaction of aryl iodides with trimethylsilylacetylene in the presence of a catalytic amount of PdBr2 gives 6-aryl-1,3-bis(trimethylsilyl)fulvenes in good to excellent yields with complete regio- and stereoselectivity. The reaction involves trimerization of trimethylsilylacetylene and cleavage of one silyl group. The silylated fulvenes obtained could be converted

  已开发出一种有效的合成路线，以合成（E）-1,3-双甲硅烷基-6-芳基富烯。在催化量的PdBr 2存在下，芳基碘化物与三甲基甲硅烷基乙炔的反应以良好的收率和优异的收率以及完全的区域选择性和立体选择性得到6-芳基-1,3-双（三甲基甲硅烷基）富烯酸酯。该反应包括三甲基甲硅烷基乙炔的三聚和一个甲硅烷基的裂解。所获得的甲硅烷基化的富烯可以通过位点选择性卤代甲硅烷基化转化为卤代的富烯。卤化的富烯通入Stille偶联，产生相应的芳基化的富通。
• New Stereoselective Synthesis of (<i>Z</i>)-α-Iodovinylsilanes via One-Pot Iododesilylation/Isomerization of 1,1-Bis(silyl)alk-1-enes
  作者：Bogdan Marciniec、Piotr Pawluć、Martyna Madalska、Grzegorz Hreczycho

  DOI：10.1055/s-0028-1083207

  日期：2008.11

  silylethenes were prepared in good to excellent yields via one-pot monolododesilylation/isomerization of readily accessible 2-aryl-1,1-bis(silyl)ethenes using N-iodosuccinimide or bis(pyridine)iodonium tetrafluoroborate under mild conditions.

  合成有用的 (Z)-2-aryl-l-iodo-1-silylethenes 通过使用 N- 容易获得的 2-aryl-1,1-bis(silyl) 乙烯的一锅单碘去甲硅烷基化/异构化以良好至优异的产率制备在温和条件下使用碘代琥珀酰亚胺或双（吡啶）碘鎓四氟硼酸盐。
• Cobalt‐Catalyzed Asymmetric Aza‐Nozaki–Hiyama–Kishi (NHK) Reaction of α‐Imino Esters with Alkenyl Halides
  作者：Tingting Xia、Yinhui Wu、Jiangtao Hu、Xianqing Wu、Jingping Qu、Yifeng Chen

  DOI：10.1002/anie.202316012

  日期：2024.2.12

  The cobalt-catalyzed aza-NHK (Nozaki–Hiyama–Kishi) reaction of ketimine has been realized to access diverse α-tertiary vinylic amino esters with excellent enantioselectivity and broad functional group tolerance. Notably, both configuration of alkenyl halide provides the same stereochemical outcome of chiral α-alkenyl quaternary amino ester, indicating that isomerization of alkenyl fragment might be

  钴催化的酮亚胺氮杂-NHK（Nozaki-Hiyama-Kishi）反应已实现，可得到多种具有优异对映选择性和广泛官能团耐受性的α-叔乙烯基氨基酯。值得注意的是，烯基卤化物的两种构型提供了与手性α-烯基季氨基酯相同的立体化学结果，表明烯基片段的异构化可能参与催化循环。
• Charge-directed conjugate addition reactions of silylated .alpha.,.beta.-unsaturated amidate anions
  作者：Manning P. Cooke、Charles M. Pollock

  DOI：10.1021/jo00078a028

  日期：1993.12

  A variety of N-substituted alpha-silylated-alpha,beta-unsaturated amidate anions (2) have been found to be excellent Michael acceptors in charge-directed conjugate addition reactions with Grignard and organolithium reagents. The effects of olefin substitution, Si-substitution, N-substitution, and amidate counterion have been studied. Anionic acceptors may be prepared in situ by the addition of silylated vinyllithium reagents to isocyanates and then allowed to undergo conjugate addition reactions with subsequently added nucleophiles, but it was found to be more efficient to isolate neutral acceptors and regenerate the acceptor anion through the use of excess nucleophile. Beta-Substituted acceptors were found to react only with reactive organolithium reagents while a beta,beta-disubstituted acceptor failed to undergo conjugate addition reactions. A primary amide acceptor (14d) also undergoes addition reactions with larger quantitites of nucleophiles suggesting that dianionic amidate acceptors (31) are involved. Diene acceptor 24 was found to undergo a 1,6-addition reaction with n-BuLi. Sodium and potassium amidate salts were found to be inferior to lithium and magnesium salts in addition reactions in keeping with the expectation that an increase in carbonyl-group charge burden retards conjugate reactions. Triphenylsilyl-containing acceptor 16 was found to be more reactive in reactions with n-BuMgCl but less reactive with bulkier tert-BuMgCl. Adduct dianions can be monoalkylated with alkyl iodides and used in Peterson olefination reactions.
• COOKE, MANNING P. , JR., J. ORG. CHEM., 52,(1987) N 26, 5729-5733
  作者：COOKE, MANNING P. , JR.

  DOI：——

  日期：——