N-benzyl-N-phenylchloroacetamide | 2653-14-7

• 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-benzyl-N-phenylchloroacetamide
• 英文别名: N-Benzylchloracetanilid；N-benzylchloroacetanilide；N-benzyl-2-chloro-N-phenylacetamide
• CAS: 2653-14-7
• 化学式: C₁₅H₁₄ClNO
• mdl: MFCD00438626
• 分子量: 259.735
• InChiKey: CFSKJDUGDLZDTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-phenylchloroacetamide 在 palladium diacetate 、 三乙胺 、 2-(二叔丁基膦)联苯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以98%的产率得到1-苄基-3H-吲哚-2-酮
  参考文献：
  名称：

  通过钯催化的 C-H 官能化从 α-氯乙酰苯胺合成取代的羟吲哚

  摘要：

  描述了一种合成羟吲哚的新方法。在催化乙酸钯和 2-（二叔丁基膦）联苯的存在下，使用三乙胺作为化学计量碱，α-氯乙酰苯胺以良好至极好的收率转化为羟吲哚，并具有高官能团相容性。环化具有高度区域选择性，无需预官能化芳烃。讨论了可能的反应机理途径。

  DOI：

  10.1021/ja037546g
• 作为产物：
  描述：

  苯甲醛 在 三氯硅烷 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 N-benzyl-N-phenylchloroacetamide
  参考文献：
  名称：

  One-Step Hydroamidation of a Schiff Base with Trichlorosilane

  摘要：

  我们已经发现，将席夫碱（2）与三氯硅烷和氯乙酰氯进行处理，可以高产率地得到一种活性极高的氯乙酰胺类除草剂（1）。这种席夫碱的一步水合酰胺化反应是一种有用的合成方法。

  DOI：

  10.1246/bcsj.64.2128

文献信息

• A definitive synthesis of 2-[(5-methyl-<i>s</i>-triazolo[4,3-<i>c</i>]quinazolin-3-yl)thio]-<i>N</i>-benzylacetanilide and other reactions of its precursors
  作者：Elli Smakula Hand、David C. Baker

  DOI：10.1139/v84-439

  日期：1984.11.1

  Treatment of 2-methyl-4-chloroquinazoline 2 with hydrazine gave 2-methyl-4-hydrazinoquinazoline 3 which was converted to 5-methyl-3-mercapto-s-triazolo[4,3-c]quinazoline 4, followed by S-alkylation with chloro-N-benzylacetanilide to give 6. The hydrazine 3 was converted to the hydrazone 9 with acetone, to 3,5-dimethyltriazolo[4,3-c]-quinazoline 10 with acetic anhydride, and to 5-methyl-s-tetrazolo[1,5-c]-quinazoline 12 via a nitroso intermediate 11 with nitrous acid. Compound 3 and its derivatives 4, 6, 10, and 12 differed from those alleged to have these structures. The previously reported compounds cannot have these structures since X-ray diffraction studies established that the structure of the common precursor is 3. The mercaptotriazole 4 was air oxidized to the disulfide 20 and hydrolyzed to 2-methyl-3-hydrazinothiocarbony]-4(3H)-quinazolinone 19. The reaction of 4 with carbon disulfide gave a side-product for which the 5-methylquinazolino[3,4-c]-1,2,4-thiadiazol-2-thione 21 is suggested. The ¹H nmr chemical shifts of the quinazoline methyl substituent are near δ 3 ppm in the fully aromatic compounds and at higher field when the heterocycle is non-aromatic.

  2-甲基-4-氯喹唑啉（2）与肼的反应生成了2-甲基-4-肼基喹唑啉（3），后者转化为5-甲基-3-巯基-s-三唑[4,3-c]喹唑啉（4），接着与氯代-N-苄基乙酰苯胺进行S-烷基化反应得到6。肼（3）与丙酮反应转化为腙（9），与乙酸酐反应转化为3,5-二甲基三唑[4,3-c]喹唑啉（10），并通过与亚硝酸的硝化中间体（11）反应转化为5-甲基-s-四唑[1,5-c]喹唑啉（12）。化合物3及其衍生物4、6、10和12与据称具有这些结构的化合物不同。由于X射线衍射研究表明共同前驱体的结构是3，因此先前报道的化合物不可能是这些结构。巯基三唑（4）被空气氧化成二硫化合物20并水解为2-甲基-3-肼基硫酰基-4(3H)-喹唑啉酮19。4与二硫化碳的反应生成了一个副产品，建议为5-甲基喹唑啉[3,4-c]-1,2,4-硫二唑-2-硫酮21。在完全芳香化合物中，喹唑啉甲基取代基的1H核磁共振化学位移接近δ 3 ppm，当杂环非芳香性时，则出现在更高的场中。
• Synthesis of N-alkyl isatins via oxidative cyclization of N-alkyl 2-bromo(chloro)acetanilides
  作者：Qingwen Gui、Fenglin Dai、Jidan Liu、Peixing Chen、Zhiyong Yang、Xiang Chen、Ze Tan

  DOI：10.1039/c4ob00118d

  日期：——

  A highly efficient method for the synthesis of N-alkyl isatins starting from N-alkyl 2-bromo or 2-chloro acetanilides is described. The starting materials are easy to prepare and the yields of isatins are generally high. Operationally the reaction is very simple to run. Even though best results were obtained with a catalytic amount of CuI, the reactions of N-alkyl 2-bromo acetanilides actually performed well even in the absence of any metal catalyst.

  本文描述了一种从N-烷基2-溴或2-氯乙酰苯胺合成N-烷基靛红的高效方法。起始原料易于制备，靛红的产率通常较高。在操作上，该反应非常简单易行。尽管使用催化量的CuI可获得最佳结果，但即使在没有任何金属催化剂的情况下，N-烷基2-溴乙酰苯胺的反应也能良好进行。
• Palladium-catalyzed olefination of aryl/alkyl halides with trimethylsilyldiazomethane <i>via</i> carbene migratory insertion
  作者：Qiu-Chao Mu、Xing-Ben Wang、Fei Ye、Yu-Li Sun、Xing-Feng Bai、Jing Chen、Chun-Gu Xia、Li-Wen Xu

  DOI：10.1039/c8cc07664b

  日期：——

  The direct olefination of aryl/alkyl halides with trimethylsilyldiazomethane (TMSD) as a C1- or C2-unit was achieved successfully via a metal carbene migratory insertion process, which offered a new access to afford (E)-vinyl silanes and (E)-silyl-substituted α,β-unsaturated amides in good yields and high chemoselectivity.

  通过金属卡宾迁移插入过程成功实现了将芳基/烷基卤化物与三甲基甲硅烷基重氮甲烷（TMSD）作为C1-或C2-单元的直接烯烃化，这为提供（E）-乙烯基硅烷和（E）-甲硅烷基取代的α，β-不饱和酰胺，收率高，化学选择性高。
• Long-term effects of lime application on 15N availability to Sitka spruce seedlings growing in pots containing peat soils
  作者：M. Kakei

  DOI：10.1093/forestry/73.4.393

  日期：2000.4.1

  The long-term effects of liming a peat soil on nitrogen availability to 3-year-old Picea sitchensis seedlings were assessed in greenhouse experiments. Seedlings were planted in pots containing either unlimed or limed peat soils that had been limed 28 years earlier. The plants were harvested in October 1993, April 1994 and July 1994 with these dates representing 100, 160 and 263 days after planting respectively. Concentration of extractable NO 3 – in the limed peat was higher than in the unlimed peat. Liming also resulted in increases in extractable organic N and total extractable N in the peat. On all harvesting occasions, percentage 15 N utilization and total N were reduced in plants grown on the limed peat. Decreased concentrations of N in the fine-root fractions were apparent for plants grown on the limed peat at the October and July harvests only. During the growing season, the above-ground parts of the plant were the dominant sinks for nitrogen. The needles and fine roots were the major fractions for the utilization of 15N particularly in April and July. The only effect of a limed peat on dry weight of plant fractions was a decrease in fine-root dry weight when plants were examined in October 1993. On all harvesting occasions, populations of mycorrhizae were decreased and roots were blackened for plants grown in the limed peat soil.

  温室实验评估了泥炭土加石灰对 3 年树龄的西洋杉幼苗氮素可用性的长期影响。幼苗被种植在装有未施石灰或已施石灰泥炭土的花盆中，这些泥炭土在 28 年前已经施过石灰。植物分别于 1993 年 10 月、1994 年 4 月和 1994 年 7 月收割，收割日期分别为种植后 100 天、160 天和 263 天。施过石灰的泥炭中的可萃取 NO 3 - 浓度高于未施石灰的泥炭。泥炭中的可萃取有机氮和总可萃取氮含量也随之增加。在所有采收期，在施过石灰的泥炭上生长的植物的氮利用率和氮总量都有所下降。仅在十月和七月收获时，生长在施过石灰的泥炭上的植物细根部分的氮浓度明显下降。在生长季节，植物的地上部分是氮的主要吸收汇。针叶和细根是利用 15N 的主要部分，尤其是在四月和七月。在 1993 年 10 月对植物进行检查时，施加了石灰的泥炭对植物各部分干重的唯一影响是细根干重减少。在所有收获季节，在石灰化泥炭土中生长的植物的菌根数量都有所减少，根部变黑。
• Carbacyclin analogs
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04680307A1

  公开（公告）日：1987-07-14

  A compound of the formula: ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group, Y.sup.1 is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or C.sub.1 -C.sub.4 alkyl group), ##STR4## (R.sup.6 is as defined above), ##STR5## R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a shingle linkage to from a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, R.sup.5 is a hydrogen atom, a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.12 alkenyl group, a C.sub.2 -C.sub.12 alkynyl group, a C.sub.3 -C.sub.10 cycloalkyl group, a C.sub.4 -C.sub.10 cycloalkenyl group, a hydroxy C.sub.1 -C.sub.12 alkyl group, a C.sub.3 -C.sub.10 heterocyclic group, a phenyl group optionally substituted with a halogen atom; a hydroxyl group, a C.sub.1 -C.sub.4 alkyl group, a trifluoromethyl group, or a C.sub.1 -C.sub.4 alkyl group or a formula: A-B (A is a C.sub.1 -C.sub.7 alkylene chain and B is a C.sub.3 -C.sub.10 cycloalkyl group, a C.sub.4 -C.sub.10 cycloalkenyl group, a C.sub.1 -C.sub.12 alkoxy group, a C.sub.3 -C.sub.10 cycloalkoxy group, a C.sub.4 -C.sub.10 cycloalkenyloxy group, a C.sub.3 -C.sub.10 heterocyclic group, or a phenyl or phenoxy group optionally substituted with a halogen atom, a hydroxy group, a C.sub.1 -C.sub.4 alkyl group, a trifluoromethyl group or a C.sub.1 -C.sub.4 alkoxy group); or a non-toxic pharmaceutically acceptable salt thereof. Said compound have strong anti-ulcerous action or antithrombotic action, and are useful in treatment of ulcer or thrombosis.

  一种化合物的公式：##STR1## 其中X.sup.1是自由的或酯化的羧基，或者是公式：##STR2## (R.sup.a和R.sup.b各自独立地是氢原子，C.sub.1-C.sub.4烷基，C.sub.3-C.sub.7环烷基，苄基，苯基，取代有卤素原子或C.sub.1-C.sub.4烷基的苯基，或者与它们相邻的氮原子一起取代一个5至7个成员的饱和杂环基团，Y.sup.1是公式：##STR3## (R.sup.6是氢原子或C.sub.1-C.sub.4烷基)，##STR4## (R.sup.6如上所定义)，##STR5## R.sup.1是氢原子，羟基或保护羟基，R.sup.2是氢原子或R.sup.1和R.sup.2当一起取代时，它们意味着在它们连接的碳原子之间形成一个双键，R.sup.3是羟基或保护羟基，R.sup.4是氢原子或C.sub.1-C.sub.4烷基，R.sup.5是氢原子，C.sub.1-C.sub.12烷基，C.sub.2-C.sub.12烯基，C.sub.2-C.sub.12炔基，C.sub.3-C.sub.10环烷基，C.sub.4-C.sub.10环烯基，羟基C.sub.1-C.sub.12烷基，C.sub.3-C.sub.10杂环基，苯基，可选地取代有卤素原子的苯基，羟基，C.sub.1-C.sub.4烷基，三氟甲基基团，或者是公式：A-B（A是C.sub.1-C.sub.7烷基链，B是C.sub.3-C.sub.10环烷基，C.sub.4-C.sub.10环烯基，C.sub.1-C.sub.12烷氧基，C.sub.3-C.sub.10环烷氧基，C.sub.4-C.sub.10环烯氧基，C.sub.3-C.sub.10杂环基，或者是可选地取代有卤素原子，羟基，C.sub.1-C.sub.4烷基，三氟甲基基团或C.sub.1-C.sub.4烷氧基的苯基或苯氧基）；或其无毒药物可接受的盐。该化合物具有强大的抗溃疡作用或抗血栓作用，并且在溃疡或血栓的治疗中有用。