N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-nitrobenzamide | 1413802-97-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-nitrobenzamide
• 英文别名: N-(o-chlorobenzoyl)dehydroabietylamine
• CAS: 1413802-97-7
• 化学式: C₂₇H₃₄N₂O₃
• 分子量: 434.579
• InChiKey: FQVCULSAQDXRRZ-DOEKTCAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  72.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-nitrobenzamide 在 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 12.5h， 以52%的产率得到C₂₇H₃₂N₂O₄
  参考文献：
  名称：

  Synthesis and antitumour activities of a novel class of dehydroabietylamine derivatives

  摘要：

  Structural modification is still a popular and important route in the forest chemical field for finding novel tricyclic diterpenes with more potential bioactivities and broad bioactive spectra. In this study, a series of dehydroabietylamine derivatives containing tricyclic diterpene structures were synthesised through oxidation in the 7th position of ring B and nitrification in the 12th position of ring C using dehydroabietylamine as the starting material. Structures of the synthesised compounds were confirmed by IR, H-1-NMR, C-13-NMR, MS and HRMS. The cytotoxicities of these compounds against PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells by the MTT assay were investigated. The results showed that the presence of a nitro group at 12th position and a carbonyl group at 7th position resulted in an increase of cytotoxic activity. Our findings present more evidence, showing the relationship between the chemical structure and biological function.

  DOI：

  10.1080/14786419.2011.648191
• 作为产物：
  描述：

  氢化松香 、 4-硝基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-nitrobenzamide
  参考文献：
  名称：

  钯催化级联 Heck 型环化和还原氨基羰基化合成官能化酰胺

  摘要：

  已经探索了一种钯催化的 Heck/羰基环化过程来合成官能化的酰胺。通过使用硝基芳烃作为容易获得的氮源，以中等至优异的收率获得了多种酰胺产品，并具有良好的官能团相容性。此外，该协议还实现了对天然分子的后期修饰。

  DOI：

  10.1039/d2ob00299j

文献信息

• A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
  作者：Zhi-Peng Bao、Ren-Guan Miao、Xinxin Qi、Xiao-Feng Wu

  DOI：10.1039/d1cc00047k

  日期：——

  Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6 acts both a CO source and a reductant here.

  碳酸二甲酯（DMC）是一种由CO 2制备的环保型化合物，具有多种反应活性。在这种交流中，已经开发了一种有效的方法，该方法使用DMC作为C1的结构单元和与硝基化合物的氨基羰基化反应中的溶剂。在此，W（CO）6既充当CO源又充当还原剂。
• Palladium-catalyzed Heck/aminocarbonylation of alkene-tethered carbamoyl chlorides with nitro compounds for the synthesis of carbamoyl-substituted oxindoles
  作者：Xing-Feng Pan、Xuanzhang Bao、Ren-Rui Xu、Xinxin Qi、Xiao-Feng Wu

  DOI：10.1039/d3ob01004j

  日期：——

  A straightforward and efficient approach for the synthesis of carbamoyl-substituted oxindoles has been developed via a palladium-catalyzed Heck cyclization and reductive aminocarbonylation reaction of alkene-tethered carbamoyl chlorides with nitro compounds. The reaction showed good compatibility toward versatile functional groups, and both nitroarenes and nitroalkanes were well tolerated. Using Mo(CO)6

  通过钯催化的 Heck 环化和烯烃束缚的氨基甲酰氯与硝基化合物的还原氨基羰基化反应，开发了一种直接有效的合成氨基甲酰基取代的羟吲哚的方法。该反应对多种官能团表现出良好的相容性，硝基芳烃和硝基烷烃均具有良好的耐受性。使用Mo(CO) 6作为固体CO源，在没有外部还原剂的情况下，以中等到高产率获得了多种氨基甲酰基取代的羟吲哚。
• Synthesis of amides-substituted 2H-benzopyrans through palladium-catalyzed one-pot aminocarbonylation reaction with nitro compounds as the nitrogen sources
  作者：Xing-Feng Pan、Pengfei Ji、Xinxin Qi、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2024.115730

  日期：2024.10

  An efficient and straightforward procedure toward the synthesis of amides-substituted 2-benzopyrans has been explored through palladium-catalyzed one-pot aminocarbonylation reaction. By using nitro compounds as attractive nitrogen sources, with Mo(CO) as both CO source and reductant, a variety of amides-containing 2-benzopyrans were obtained in moderate to high yields with good functional group tolerance

  通过钯催化的一锅氨基羰基化反应，探索了一种有效且简单的合成酰胺取代的 2-苯并吡喃的方法。以硝基化合物为有吸引力的氮源，以Mo(CO)作为CO源和还原剂，以中等到高产率获得了多种含酰胺的2-苯并吡喃，且具有良好的官能团耐受性。该协议具有原子经济性、无需操作有毒CO气体和广泛的底物范围等优点。