2-(cinnamyloxy)acetonitrile | 474003-57-1

• 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: 2-(cinnamyloxy)acetonitrile
• 英文别名: {[(2E)-3-phenyl-2-propenyl]oxy}acetonitrile；2-[(E)-3-phenylprop-2-enoxy]acetonitrile
• CAS: 474003-57-1
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: NCCQCIAYLKHTPZ-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(cinnamyloxy)acetonitrile 在 4 A molecular sieve N-溴代丁二酰亚胺(NBS) 、 叠氮基三甲基硅烷 、 zinc trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(3-azido-2-bromo-3-phenylpropyloxy)-acetonitrile
  参考文献：
  名称：

  金属三氟甲磺酸酯催化的烯烃，NBS，腈和TMSN 3的反应：1,5-二取代的四唑的合成

  摘要：

  通过金属三氟甲磺酸酯催化烯烃，NBS，腈和TMSN 3的一锅反应，已开发出一种通用且高效的合成1,5-二取代四唑的方法。在金属三氟甲磺酸酯中，发现Zn（OTf）2是最好的催化剂。烯烃和腈的不同组合的使用产生了各种1，5-二取代的四唑，其含有N 1-烷基取代基的另外的α-溴官能度。

  DOI：

  10.1021/jo062432j
• 作为产物：
  描述：

  (E)-(3-phenylprop-2-enyloxy)acetaldehyde 在 盐酸羟胺 、 copper(II) bis(trifluoromethanesulfonate) 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 2-(cinnamyloxy)acetonitrile
  参考文献：
  名称：

  Intramolecular Cycloaddition of O-tert-Butyldimethylsilyloximes in the Presence of BF₃·OEt₂

  摘要：

  Intramolecular cycloaddition of novel 1,3-dipoles, N-boranonitrones, was examined. Treatment of O-tert-butyldimethylsilyloximes 9-12 having olefin moieties with 2 equiv of BF3 center dot OEt2 generated N-boranonitrones, which underwent intramolecular cycloaddition to afford N-nonsubstituted cycloadducts 16 (and/or 18) after extractive workup. Despite the Lewis-acidic conditions, the olefin geometry of the substrates was retained in the cycloadducts in the present cycloaddition. The electronic nature of the N-boranonitrones appeared to be electrophilic. In the case of substrate 11c, having an electron-donating methyl group at an internal position of the olefin moiety, the cycloaddition gave the bridged cycloadduct 18b. The cycloaddition proceeded at relatively low temperature, and the diastereoselectivity was high.

  DOI：

  10.1021/jo051652e

文献信息

• Photoredox-Catalyzed Intermolecular Remote C–H and C–C Vinylation via Iminyl Radicals
  作者：Xu Shen、Jia-Jia Zhao、Shouyun Yu

  DOI：10.1021/acs.orglett.8b02540

  日期：2018.9.7

  C(sp3)–H and C–C vinylation of O-acyl oximes with vinyl boronic acids has been achieved. This strategy is enabled by photoreductive generation of iminyl radicals from O-acyl oximes under irradiation by visible light. The translocated carbon-centered radicals, which are generated from the iminyl radicals through 1,5-hydrogen atom transfer or C–C cleavage, can be vinylated with vinyl boronic acids. This

  已经实现了用乙烯基硼酸对O-酰基肟进行分子间远程C（sp 3）–H和C–C乙烯基化的统一策略。该策略通过在可见光照射下从O-酰基肟光还原生成亚胺基而实现。亚胺基自由基通过1，5-氢原子转移或CC裂解产生的碳中心自由基可以用乙烯基硼酸乙烯基化。该策略为通过C（sp 3）–H和C–C裂解进行远程官能化开辟了新途径，并为合成酮和腈的γ-乙烯基化提供了一种高效且通用的解决方案。
• 10.1021/acs.joc.4c00703
  作者：Yang, Sen、Cai, Sha-Sha、Li, Jun-Hua、Chen, Ming

  DOI：10.1021/acs.joc.4c00703

  日期：——

  A palladium-catalyzed radical Heck-type coupling reaction of cyclobutanone oxime esters with olefins under visible-light irradiation has been developed. The cyanoalkyl/Pd(I) hybrid species generated by selected ring-opening C–C bond cleavage of imino/Pd(I) species reacted smoothly with vinyl arenes, delivering the cyanoalkylation olefins under mild conditions. This elegant strategy has a broad scope

  开发了一种在可见光照射下钯催化的环丁酮肟酯与烯烃的自由基 Heck 型偶联反应。通过亚氨基/Pd(I)物质的选择性开环C-C键断裂产生的氰基烷基/Pd(I)杂化物质与乙烯基芳烃顺利反应，在温和条件下产生氰基烷基化烯烃。这种优雅的策略具有广泛的范围和功能组的容忍度。随后，生物活性分子的后期功能化和产品的合成转化进一步证实了实用性。
• Iminyl-Radical-Promoted C–C Bond Cleavage/Heck-Like Coupling via Dual Cobaloxime and Photoredox Catalysis
  作者：Jia-Lin Tu、Wan Tang、Wei Xu、Feng Liu

  DOI：10.1021/acs.joc.0c02834

  日期：2021.2.5
• KULKA K.; ZAZULA T.; YORECKO J. M., 7 INT. CONGR. ESSENTIAL OILS, KYOTO, 1977. S. L., 1979, 259-262
  作者：KULKA K.、 ZAZULA T.、 YORECKO J. M.

  DOI：——

  日期：——
• Intramolecular Cycloaddition of <i>O</i>-<i>tert</i>-Butyldimethylsilyloximes in the Presence of BF₃·OEt₂
  作者：Osamu Tamura、Takahiro Mitsuya、Xin Huang、Yoshiyuki Tsutsumi、Sanae Hattori、Hiroyuki Ishibashi

  DOI：10.1021/jo051652e

  日期：2005.12.1

  Intramolecular cycloaddition of novel 1,3-dipoles, N-boranonitrones, was examined. Treatment of O-tert-butyldimethylsilyloximes 9-12 having olefin moieties with 2 equiv of BF3 center dot OEt2 generated N-boranonitrones, which underwent intramolecular cycloaddition to afford N-nonsubstituted cycloadducts 16 (and/or 18) after extractive workup. Despite the Lewis-acidic conditions, the olefin geometry of the substrates was retained in the cycloadducts in the present cycloaddition. The electronic nature of the N-boranonitrones appeared to be electrophilic. In the case of substrate 11c, having an electron-donating methyl group at an internal position of the olefin moiety, the cycloaddition gave the bridged cycloadduct 18b. The cycloaddition proceeded at relatively low temperature, and the diastereoselectivity was high.