4-Pentenyl 4-nitrobenzoate | 6747-63-3

• 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: 4-Pentenyl 4-nitrobenzoate
• 英文别名: pent-4-en-1-yl 4-nitrobenzoate；p-nitrophenyl 4-pentenyl carbonate；pent-4-enyl 4-nitrobenzoate
• CAS: 6747-63-3
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: UFYGZXVKAMZTBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Pentenyl 4-nitrobenzoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以86%的产率得到1,2-Epoxypentyl 4-nitrobenzoate
  参考文献：
  名称：

  Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C-Ethylenediamine Catalyst and THF

  摘要：

  In general, palladium-carbon (Pd/C) catalyzed hydrogenation of epoxides affords the corresponding primary and secondary alcohols as a mixture. It has been found that the catalytic activity of a Pd/C -ethylenediamine complex catalyst [Pd/C(en)] in the hydrogenolysis of epoxide functions is drastically reduced. Herein we describe a mild and chemoselective method for the hydrogenation of olefin, nitro, and azide functions with retention of the epoxide function. The chemoselectivity was accomplished by using a combination of 5% Pd/C(en) and THF as solvent. A significant drop in the chemoselectivity of the hydrogenation is observed with 5% Pd/C(en) in MeOH. These results reinforce the utility of epoxides as important precursors of alcohols in synthetic chemistry.

  DOI：

  10.1002/1521-3765(20000616)6:12<2200::aid-chem2200>3.0.co;2-3
• 作为产物：
  描述：

  4-戊烯-1-醇 、 4-硝基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到4-Pentenyl 4-nitrobenzoate
  参考文献：
  名称：

  碱促进的未活化烯烃的自由基偶氮氟甲基化。

  摘要：

  芳基重氮盐与可商购获得的CF 3 SO 2 Na / CF 2 HSO 2 Na的碱诱导反应可以生成相应的重氮基和氟甲基。将氟甲基自由基加到烯烃中，随后进行重氮捕集，可提供良好至极佳收率的偶氮氟甲基化产物。这种在温和反应条件下的无金属方法具有广泛的官能团相容性，可用于各种天然产物和生物活性分子的后期修饰。

  DOI：

  10.1021/acs.orglett.0c01395

文献信息

• Widely Applicable Hydrofluorination of Alkenes via Bifunctional Activation of Hydrogen Fluoride
  作者：Zhichao Lu、Xiaojun Zeng、Gerald B. Hammond、Bo Xu

  DOI：10.1021/jacs.7b12704

  日期：2017.12.20

  Expanding the use of fluorine in pharmaceuticals, agrochemicals and materials requires a widely applicable and more efficient protocol for the preparation of fluorinated compounds. We have developed a new generation nucleophilic fluorination reagent, KHSO4-13HF, HF 68 wt/wt %, that is not only easily handled and inexpensive but also capable of hydrofluorinating diverse, highly functionalized alkenes

  扩大氟在药物、农用化学品和材料中的使用需要一种广泛适用且更有效的氟化化合物制备方案。我们开发了新一代亲核氟化试剂 KHSO4-13HF, HF 68 wt/wt %，不仅易于操作且价格低廉，而且能够对包括天然产物在内的多种高功能化烯烃进行氢氟化。该反应的高效率取决于使用高度“酸性”氢键受体激活 HF。
• N‐Heterocyclic Carbene Catalyzed Ester Synthesis from Organic Halides through Incorporation of Oxygen Atoms from Air
  作者：Hui Tan、Shen‐An Wang、Zixi Yan、Jianzhong Liu、Jialiang Wei、Song Song、Ning Jiao

  DOI：10.1002/anie.202011039

  日期：2021.1.25

  Oxygenation reactions with molecular oxygen (O2) as the oxygen source provides a green and straightforward strategy for the construction of O‐containing compounds. Demonstrated here is a novel N‐heterocyclic carbene (NHC) catalyzed oxidative transformation of simple and readily available organic halides into valuable esters through the incorporation of O‐atoms from O2. Mechanistic studies prove that

  以分子氧（O 2）为氧源的加氧反应为构建含O化合物提供了绿色而直接的策略。这里展示的是一种新颖的N杂环卡宾（NHC）通过将O 2中的O原子并入，将简单易用的有机卤化物催化氧化转化为有价值的酯的方法。机理研究证明，原位产生的脱氧Breslow中间体被氧化为Breslow中间体，通过该氧化方案进一步转化。该方法拓宽了NHC催化领域，并促进了与O 2的氧化反应。
• Iodotrifluoromethylation of Alkenes and Alkynes with Sodium Trifluoromethanesulfinate and Iodine Pentoxide
  作者：Zhaojia Hang、Zejiang Li、Zhong-Quan Liu

  DOI：10.1021/ol501380e

  日期：2014.7.18

  A scalable, selective, and operationally easy iodotrifluoromethylation of a wide range of alkenes and alkynes by using two simple and safe solids, sodium trifluoromethanesulfinate and iodine pentoxide, in aqueous medium has been developed. Mechanistic studies confirm that free-radical processes are involved in this system since the key radical intermediates such as CF3 and β-CF3 alkyl radicals have

  通过在水性介质中使用两种简单且安全的固体三氟甲烷亚磺酸钠和五氧化二碘，开发了可扩展，选择性且操作简便的各种烯烃和炔烃的碘三氟甲基化方法。机理的研究证实，因为键的自由基中间体如CF自由基方法涉及在该系统中3和β-CF 3个烷基具有通过旋捕获和电子自旋共振被清楚地检测到。
• METHODS OF HYDROFLUORINATION
  申请人：UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC.

  公开号：US20190176134A1

  公开（公告）日：2019-06-13

  Some embodiments of the invention include inventive catalysts (e.g., compounds of Formula (I) or (Ia)). Other embodiments include compositions comprising the inventive catalysts. Some embodiments include methods of using the inventive catalysts (e.g., in hydrofluorination of an organic compound). Further embodiments include methods for making the inventive catalysts. Additional embodiments of the invention are also discussed herein.

  本发明的一些实施例包括创新催化剂（例如，化合物的化学式（I）或（Ia））。其他实施例包括包含创新催化剂的组合物。一些实施例包括使用创新催化剂的方法（例如，在有机化合物的氢氟化反应中）。进一步的实施例包括制备创新催化剂的方法。本发明的其他实施例也在本文中讨论。
• Copper-Catalyzed Bromodifluoroacetylation of Alkenes with Ethyl Bromodifluoroacetate
  作者：Dengke Li、Tingting Mao、Jinbo Huang、Qiang Zhu

  DOI：10.1021/acs.joc.8b01434

  日期：2018.9.7

  ethyl bromodifluoroacetate (BrCF2CO2Et) as a difluoroacetylating reagent, has been disclosed. The reaction proceeds under mild conditions, and possible byproducts generated from hydrodifluoroacetylation and/or direct alkenyl C–H difluoroacetylation are not observed. Mechanistic studies confirm that the atom transfer radical addition (ATRA) process is involved in this alkene difunctionalization reaction

  已经公开了使用溴二氟乙酸乙酯（BrCF 2 CO 2 Et）作为二氟乙酰化试剂的Cu催化的烯烃的区域选择性溴二氟乙酰化。该反应在温和的条件下进行，未观察到氢二氟乙酰化和/或直接烯基CH二氟乙酰化产生的副产物。机理研究证实，该烯烃双官能化反应涉及原子转移自由基加成（ATRA）过程。