N-(hex-5-enyl)benzamide | 113261-23-7

• 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: N-(hex-5-enyl)benzamide
• 英文别名: N-hex-5-enylbenzamide
• CAS: 113261-23-7
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: NKQKRVSUTDJVGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(hex-5-enyl)benzamide 在 PyBH2I 、 sodium perborate 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到6-苄氨基-1-己醇
  参考文献：
  名称：

  Hydroboration with Pyridine Borane at Room Temperature

  摘要：

  Treatment of pyridine borane (Py.BH3) with iodine, bromine, or strong acids affords activated Py.BH2X complexes that are capable of hydroborating alkenes at room temperature. Evidence is presented for an unusual hydroboration mechanism involving leaving group displacement. In contrast to THF.BH3, hydroboration with Py.BH2I selectively affords the monoadducts. The crude hydroboration products are converted into synthetically useful potassium alkyltrifluoroborate salts upon treatment with methanolic KHF2.

  DOI：

  10.1021/ja043743j
• 作为产物：
  描述：

  5-己烯腈 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 生成 N-(hex-5-enyl)benzamide
  参考文献：
  名称：

  Samii, Zakaria K. M. Abd El; Ashmawy, Mohamed I. Al; Mellor, John M., Journal of the Chemical Society. Perkin transactions I, 1988, p. 2517 - 2522

  摘要：

  DOI：

文献信息

• Defined Hypervalent Iodine(III) Reagents Incorporating Transferable Nitrogen Groups: Nucleophilic Amination through Electrophilic Activation
  作者：José A. Souto、Claudio Martínez、Irene Velilla、Kilian Muñiz

  DOI：10.1002/anie.201206420

  日期：2013.1.21

  Only I and N: Hypervalent iodine(III) reagents with two reactive IN single bonds have been isolated for the first time. Their solid‐state and solution structures provide evidence for enhanced electrophilicity at iodine and nucleophilic character of the imine. As a result, improved reactivity in amination reactions and unprecedented nitrogen‐transfer reactions under metal‐free conditions are realized

  仅1和N：高价碘（III）与两个反应性我试剂 N个单键已经被分离的第一次。它们的固态和溶液结构为碘的亲电子性和亚胺的亲核性提供了证据。结果，实现了在无金属条件下提高了胺化反应的反应性和前所未有的氮转移反应。
• Mn(OAc)₃-Mediated Addition Reactions of NaSO₂CF₃ and Perhalogenated Carboxylic Acids with Unactivated Alkenes Conjectured by a Single Electron Transfer and Halogen Abstraction Mechanism
  作者：Hui Sun、Guannan Cui、Huijian Shang、Bin Cui

  DOI：10.1021/acs.joc.0c02086

  日期：2020.12.4

  Mn(OAc)3·2H2O, CF3SO2Na, and perhalogenated carboxylic acids has been achieved. Perhalogenated carboxylic acids act as a halogen source and CF3SO2Na acts as a CF3 source. The reaction displayed good tolerance of functional groups in the substrates under mild conditions. The radical clock experiment and TEMPO inhibition experiment support a radical process. The halogen reagent competition experiment shows that the

  通过使用Mn（OAc）3 ·2H 2 O，CF 3 SO 2 Na和全卤代羧酸，可以实现烯烃的自由基卤代三氟甲基化。全卤代羧酸充当卤素源，CF 3 SO 2 Na充当CF 3源。该反应在温和条件下对底物中的官能团表现出良好的耐受性。自由基时钟实验和TEMPO抑制实验支持自由基过程。卤素试剂竞争实验表明，卤化过程的最后一步主要是通过卤素提取机理。
• Mn(OAc)₃-Mediated Hydrotrifluoromethylation of Unactivated Alkenes Using CF₃SO₂Na as the Trifluoromethyl Source
  作者：Bin Cui、Hui Sun、Yibo Xu、Lin Li、Lili Duan、Yue-Ming Li

  DOI：10.1021/acs.joc.8b00633

  日期：2018.6.1

  A simple and efficient method for hydrotrifluoromethylation of unactivated alkenes was reported. The reaction relied on the single electron oxidation of a commercially available sodium trifluoromethanesulfinate (CF3SO2Na, Langlois’ reagent) using Mn(OAc)3·2H2O as the oxidant and the subsequent addition of trifluoromethyl radical to C═C double bonds. The reaction proceeded readily under mild conditions

  报道了一种简单有效的未活化烯烃加氢三氟甲基化的方法。该反应依赖于使用Mn（OAc）3 ·2H 2 O作为氧化剂的市售三氟甲烷亚磺酸钠（CF 3 SO 2 Na，Langlois试剂）的单电子氧化，随后将三氟甲基自由基加到C═Cdouble债券。反应在温和条件下容易进行，并且对底物中的各种官能团具有良好的耐受性。通过氘化，自由基钟和TEMPO抑制实验研究了初步反应机理。
• New routes to heterocycles via sulphenylation of unsaturated amides
  作者：Zakaria KM Abd El Samii、Mohamed I Al Ashmawy、John M. Mellor

  DOI：10.1016/s0040-4039(00)96017-9

  日期：1987.1

  Reaction of manganic acetate with organic disulphides in dichloromethane-trifluoroacetic acid in the presence of a variety of unsaturated amides leads to intramolecular cyclisation with formation of sulphenylated oxazolines, oxazines or tetrahydropyrroles.

  在各种不饱和酰胺存在下，乙酸锰与有机二硫化物在二氯甲烷-三氟乙酸中的反应导致分子内环化，形成亚硫酰基化的恶唑啉，恶嗪或四氢吡咯。
• Nickel-Catalyzed Remote C(sp³)–N/O Bond Formation of Alkenes with Unactivated Amines and Alcohols
  作者：Tao Song、Yicong Luo、Kuiyang Wang、Bingyi Wang、Qianjia Yuan、Wanbin Zhang

  DOI：10.1021/acscatal.3c00238

  日期：——

  Transition metal-catalyzed remote hydrofunctionalization of alkenes is an efficient method to realize C(sp3)–H functionalization. However, remote hydrofunctionalization of alkenes with unactivated amines and alcohols has not been successfully developed to date. Herein, we report an efficient nickel-catalyzed remote hydroamination and hydroetherification of alkenes with unactivated amines and alcohols, accessing

  过渡金属催化的烯烃远程加氢官能化是实现C(sp 3 )–H官能化的有效方法。然而，迄今为止尚未成功开发烯烃与未活化的胺和醇的远程加氢官能化。在此，我们报道了一种有效的镍催化的烯烃与未活化的胺和醇的远程加氢胺化和加氢醚化反应，获得了一系列具有良好至高产率（高达93%）和独特区域选择性的宝石-二胺和N , O-缩醛衍生物。机理研究和 DFT 计算表明，使用 2-iodo-2-methylpropane ( tBuI) 作为温和的氢化物源和自由基前体对于提供远程功能化产品至关重要。该研究工作提供了一种在远离烯烃双键的C(sp 3 )-H位置安装氨基或烷氧基的有效方法。