(chlorocarbonyl)benzyl ketene | 57421-93-9

• 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: (chlorocarbonyl)benzyl ketene
• 英文别名: 2-Benzyl-3-oxoprop-2-enoyl chloride
• CAS: 57421-93-9
• 化学式: C₁₀H₇ClO₂
• 分子量: 194.617
• InChiKey: VEVYVIJZKYKZFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  (chlorocarbonyl)benzyl ketene 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 1-benzyl-3,7-diphenyl-3-azabicyclo[3.1.1]heptane-2,4,6-trione
  参考文献：
  名称：

  Mesoionic 1,3-Oxazinium Olates. Rearrangement to Acylketenes and 3-Azabicyclo[3.1.1]heptanetriones

  摘要：

  Metastable but isolable mesoionic 1,3-oxazinium 4-olates 9d-f undergo ring opening to acylketenes 10 at or near room temperature. The ketenes undergo intramolecular criss-cross [2 + 2] cycloaddition to afford 3-azabicyclo[3.1.1]heptanetriones 12. The structure of 12d was established by X-ray crystallography.

  DOI：

  10.1021/jo050428m
• 作为产物：
  描述：

  苄基丙二酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到(chlorocarbonyl)benzyl ketene
  参考文献：
  名称：

  Malonates in Cyclocondensation Reactions

  摘要：

  本文描述了使用如二乙基美克酸盐9、（氯羰基）烯酮15和双（2,4,6-三氯苯基）美克酸盐18作为试剂与1,3-双核亲核试剂进行环缩合以生成六元杂环的过程。此外，进一步尝试使用如双（三甲基硅基）美克酸盐19和双（氨基亚氨基）美克酸盐29作为新的环缩合试剂的研究也进行了描述。

  DOI：

  10.3390/60400338

文献信息

• Preparation of Arylpropynamides and Their Reaction with Malonyl Acid Derivatives
  作者：Olga Petina、Igor Yakovlev、Detlef Geffken

  DOI：10.1055/s-0032-1316851

  日期：——

  4-hydroxy-2-(phenylethynyl)-6H-1,3-oxazin-6-ones; and the reaction of arylpropynamides with disubstituted malonyl chlorides furnished open-chain arylpropenamides exclusively. Synthesis of arylpropynamides and their reactions with different malonic acid derivatives is described. Treatment of arylpropynamides with unsubstituted malonyl chloride furnished N-(3-arylprop-2-ynoyl)-6-chloro-4-hydroxy-2-oxo-2H-pyran-3-carboxamides;

  摘要 描述了芳基丙炔酰胺的合成及其与不同丙二酸衍生物的反应。未取代的丙二酰氯配arylpropynamides的治疗ñ - （3- arylprop -2-炔酰基）-6-氯-4-羟基-2-氧代-2- ħ -吡喃-3-羧酰胺; 将单取代的丙二酰氯或其衍生物（氯羰基）乙基乙烯酮与芳基丙炔酰胺反应，得到4-羟基-2-（苯基乙炔基）-6 H -1,3-恶嗪-6-酮；芳基丙酰胺与二取代的丙二酰氯的反应仅提供开链芳基丙烯酰胺。 描述了芳基丙炔酰胺的合成及其与不同丙二酸衍生物的反应。未取代的丙二酰氯配arylpropynamides的治疗ñ - （3- arylprop -2-炔酰基）-6-氯-4-羟基-2-氧代-2- ħ -吡喃-3-羧酰胺; 将单取代的丙二酰氯或其衍生物（氯羰基）乙基乙烯酮与芳基丙炔酰胺反应，得到4-羟基-2-（苯基乙炔基）-6 H -1,3-恶嗪-6-酮；芳基丙酰胺与二取代的丙二酰氯的反应仅提供开链芳基丙烯酰胺。
• A Convenient One-Pot Synthesis of Pyrano[3,2-<i>c</i>]quinolin-2,5(6<i>H</i>)-dione and 2<i>H</i>,5<i>H</i>-Pyrano[3,2-<i>c</i>]chromene-2,5-dione Derivatives
  作者：Hassan Sheibani、Mohammad Hossein Mosslemin、Soheila Behzadi、Mohammad Reza Islami、Kazem Saidi

  DOI：10.1055/s-2006-926295

  日期：——

  The preparation of novel pyrano[3,2-c]quinolin-2,5(6H)-dione and 2H,5H-pyrano[3,2-c]chromene-2,5-dione derivatives starting from 4-hydroxyquinolin-2(1H)-ones and 4-hydroxy-2H-chromene-2-one with chlorocarbonyl ketenes is described. This method provides a new route to produce fused pyrano derivatives in good to excellent yields in a short experimental time.

  报道了以4-羟基喹啉-2(1H)-酮和4-羟基-2H-色烯-2-酮为起始物，通过氯代碳酰基烯酮合成新型吡喃并[3,2-c]喹啉-2,5(6H)-二酮和2H,5H-吡喃并[3,2-c]色烯-2,5-二酮衍生物的方法。该方法提供了一条在短时间内以良好至优异收率制备融合吡喃衍生物的新途径。
• Malonates in Cyclocondensation Reactions
  作者：Wolfgang Stadlbauer、El-Sayed Badawey、Gerhard Hojas、Peter Roschger、Thomas Kappe

  DOI：10.3390/60400338

  日期：——

  The use of malonates such as diethyl malonates 9, (chlorocarbonyl)ketenes 15 and bis(2,4,6-trichlorophenyl) malonates 18 as reagents for cyclocondensation with 1,3-dinucleophiles to give six-membered heterocycles is described. Further attempts to use malonates such as bis(trimethylsilyl) malonates 19 and bis(carbamimidoyl) malonates 29 as new cyclocondensation agents are described .

  本文描述了使用如二乙基美克酸盐9、（氯羰基）烯酮15和双（2,4,6-三氯苯基）美克酸盐18作为试剂与1,3-双核亲核试剂进行环缩合以生成六元杂环的过程。此外，进一步尝试使用如双（三甲基硅基）美克酸盐19和双（氨基亚氨基）美克酸盐29作为新的环缩合试剂的研究也进行了描述。
• Synthese neuer 1,3-Oxazinone aus Cyanamiden und Chlorocarbonylketenen
  作者：Walter Ried、Harald Nenninger

  DOI：10.1055/s-1990-26823

  日期：——

  Synthesis of new 1,3-Oxazinones from Chlorocarbonylketenes and Cyanamides Chlorocarbonylketenes 1a,b react with cyanamides 2a-i under mild conditions to form the 2-amino-1,3-oxazin-4-one derivatives 3a-i and 4 in mostly good yields. Treatment of compounds 3a,f with triethylamine in toluene in the presence of water or with triethylamine and benzylamine in toluene affords N-acylureas 5a,f, 2-amino-1,3-oxazin-4-ones 6, or malonamide 8, depending on the reaction conditions, whereas treatment of 3c with wet toluene leads to the formation of the 2-amino-1, 3-oxazin-6-one 7. Cycloaddition of biscyanmides 9a-c and chlorocarbonylketene 1a leads to the bis-oxazinone derivatives 10a-c in low to moderate yields; in the case of 10a, the monosubstituted product 11a is obtained as a side product.

  从氯碳酰基烯酮和氰胺合成新的1,3-氧唑酮。氯碳酰基烯酮1a,b在温和条件下与氰胺2a-i反应，主要以良好的产率形成2-氨基-1,3-氧唑-4-酮衍生物3a-i和4。化合物3a,f在存在水的甲苯中与三乙胺反应，或与三乙胺和苄胺在甲苯中反应，依赖于反应条件，可以得到N-酰基脲5a,f、2-氨基-1,3-氧唑-4-酮6或马隆酰胺8，而将3c与湿甲苯处理则会形成2-氨基-1,3-氧唑-6-酮7。双氰胺9a-c与氯碳酰基烯酮1a的环加成反应生成双氧唑酮衍生物10a-c，其产率为低至中等；在10a的情况下，单取代产物11a作为副产物生成。
• Unexpected Products from Mesoionic 1,3-Thiazinium and Oxazinium Olates: A Novel Access to 3,5-Diaryl-1,3-thiazine-2,4,6-trione and Alkoxy-3,5-diphenyl-3H-1,3-oxazine-2,6-dione Derivatives
  作者：Mahboobeh Zahedifar、Hassan Sheibani

  DOI：10.1071/ch14095

  日期：——

  4-olates II, respectively. At room temperature, appropriately substituted mesoionic 1,3-thiazinium 4-olates I eliminated the corresponding alkene with generation of 3,5-diaryl-1,3-thiazine-2,4,6-trione derivatives 3. However, the methoxy-substituted compound 5 was stable at room temperature at least for several weeks. In the case of the mesoionic1,3-oxazinium 4-olates II an alkyl group migration affords 4-alkoxy-3

  （氯羰基）的缩合烯酮1与Ñ -phenylthiocarbamates 2和Ñ -phenylcarbamates 6被假定为导致不稳定的介离子1,3-噻嗪-4- olates的形成我或1,3-恶嗪-4- olates II分别。在室温下，适当取代的介离子1,3-噻嗪-4- olates我消除了生成3,5-二芳基-1,3-噻嗪-2,4,6-三酮衍生物的相应的烯烃3。但是，甲氧基取代的化合物5在室温下至少稳定数周。就中离子的1,3-恶嗪鎓4-油酸酯而言II，烷基迁移提供4-烷氧基-3，5-二苯基-3 H -1，3-恶嗪-2，6-二酮7。