3-Chlorophenyldiazomethane | 51157-54-1

• 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: 3-Chlorophenyldiazomethane
• 英文别名: 3-Chlor-phenyl-diazomethan；3-Chlor-α-diazo-toluol；1-chloro-3-[(E)-diazomethyl]benzene
• CAS: 51157-54-1
• 化学式: C₇H₅ClN₂
• 分子量: 152.583
• InChiKey: KPOBVONGNBNGKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Chlorophenyldiazomethane 在 铜(1+)高氯酸酯 作用下， 以 乙腈 为溶剂， 反应 0.2h， 生成 trans-1,2-bis-(3-chlorophenyl)ethene
  参考文献：
  名称：

  ZEOLITE-CuNaY CATALYZED DECOMPOSITION OF ARYLDIAZOMETHANE

  摘要：

  芳基二氮甲烷的分解在铜离子交换的Y型沸石催化下高选择性地生成顺式-1,2-二芳基乙烯。催化活性和选择性受到沸石中铜离子交换水平和所用溶剂的影响。

  DOI：

  10.1246/cl.1985.1895
• 作为产物：
  描述：

  3-chlorobenzaldehyde tosylhydrazone 在 sodium methylate 作用下， 生成 3-Chlorophenyldiazomethane
  参考文献：
  名称：

  Carbenoid Formation of Arylcyclopropanes from Olefins, Benzal Bromides, and Organolithium Compounds and from Photolysis of Aryldiazomethanes

  摘要：

  DOI：

  10.1021/ja01073a029

文献信息

• Process for the preparation of an oxirane, azirdine or cyclopropane
  申请人：Zeneca Limited

  公开号：US05703246A1

  公开（公告）日：1997-12-30

  A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I) wherein, X is oxygen, NR.sup.4 or CHR.sup.5 ; R.sup.1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R.sup.2 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, CHR.sup.14 NHR.sup.13, heterocyclic or cycloalkyl; or R.sup.1 and R.sup.2 join together to form a cycloalkyl ring; R.sup.3 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, R.sup.8.sub.3 Sn, CONR.sup.8 R.sup.9 or trimethylsilyl; R.sup.4 and R.sup.5 are, independently, alkyl, cycloalkyl, aryl, heteroaromatic, SO.sub.2 R.sup.8, SO.sub.3 R.sup.8, COR.sup.8, CO.sub.2 R.sup.8, CONR.sup.8 R.sup.9 or CN, or R.sup.4 can also be P(O)(aryl).sub.2 ; R.sup.8 and R.sup.9 are independently alkyl, aryl or arylalkyl; R.sup.13 and R.sup.14 are independently hydrogen, alkyl or aryl; the process comprising reacting a mixture of a compound of formula (II), wherein R.sup.1, R.sup.2 and X are as defined above, and a sulphide of formula SR.sup.6 R.sup.7, wherein R.sup.6 and R.sup.7 are independently alkyl, aryl or heteroaomatic, or R.sup.6 and R.sup.7 join together to form a cycloalkyl ring which optionally includes an additional heteroatom, with either (i) a metallocarbon obtainable by reacting an alkylmetal with a methane derivative of formula CHR.sup.3 X'X", wherein R.sup.3 is as defined above, and X' and X" are independently, a leaving group, or (ii) a metallocarbon obtainable by reacting a compound of formula (III), (wherein R.sup.3 may not be hydrogen) with a suitable organometallic or inorganic reagent.

  一种制备式(I)的环氧烷、氮杂环丙烷或环丙烷的方法，其中，X为氧、NR^4或CHR^5；R^1为氢、烷基、芳基、杂环芳基、杂环烷基或环烷基；R^2为氢、烷基、芳基、杂环芳基、CO_2R^8、CHR^14NHR^13、杂环烷基或环烷基；或R^1和R^2结合形成环烷基环；R^3为氢、烷基、芳基、杂环芳基、CO_2R^8、R^83Sn、CONR^8R^9或三甲基硅基；R^4和R^5分别为烷基、环烷基、芳基、杂环芳基、SO_2R^8、SO_3R^8、COR^8、CO_2R^8、CONR^8R^9或CN，或R^4也可以是P(O)(芳基)_2；R^8和R^9独立地为烷基、芳基或芳基烷基；R^13和R^14独立地为氢、烷基或芳基；该方法包括将式(II)化合物的混合物与式SR^6R^7的硫化物反应，其中R^1、R^2和X如上所定义，R^6和R^7独立地为烷基、芳基或杂环芳基，或R^6和R^7结合形成环烷基环，该环可能包括额外的杂原子，与(i)通过将烷基金属与式CHR^3X'X"的甲烷衍生物反应获得的金属碳或(ii)通过将式(III)化合物（其中R^3可能不是氢）与适当的有机金属或无机试剂反应获得的金属碳反应。
• One-Pot Synthesis of 1H-Indazole-4,7-diols via Iodine(III)-Mediated [3+2] Cyclization in Water
  作者：Guangli Yu、Yingwei Hou、Chao Cai

  DOI：10.1055/s-0035-1560596

  日期：——

  An efficient route in one-pot to a new class of 1H-indazole-4,7-diols derivatives has been developed through [3+2] cycloadditive approach in water. The cycloaddition reaction was carried out via condensation of phenol and diazomethyl benzene intermediates by taking advantage of iodobenzene diacetate as an oxidant. Eighteen indazole derivatives were successfully prepared by the established method.

  通过在水中的 [3+2] 环加成方法，开发了一种一锅法制备新型 1H-吲唑-4,7-二醇衍生物的有效途径。环加成反应是利用二乙酸碘苯作为氧化剂，通过苯酚和重氮甲基苯中间体缩合进行的。采用所建立的方法成功制备了十八种吲唑衍生物。
• Base mediated 1,3-dipolar cycloaddition of α-substituted vinyl phosphonates with diazo compounds for synthesis of 3-pyrazolylphosphonates and 5-pyrazolcarboxylates
  作者：Nataliya S. Goulioukina、Nikolay N. Makukhin、Egor D. Shinkarev、Yuri K. Grishin、Vitaly A. Roznyatovsky、Irina P. Beletskaya

  DOI：10.1039/c6ob01780k

  日期：——

  5-Aryl-substituted pyrazol-3-ylphosphonates have been conveniently synthesized by 1,3-dipolar cycloaddition of 1-formamidovinylphosphonates and aryldiazomethanes under K2CO3/MeOH conditions at room temperature. These pyrazoles are formed in one pot via spontaneous elimination of formamide. Basic conditions prevent competitive formation of cyclopropylphosphonates. 3-Aryl substituted pyrazol-5-carboxylates

  通过在室温下在K 2 CO 3 / MeOH条件下将1-甲酰胺基乙烯基膦酸酯和芳基重氮甲烷进行1，3-偶极环加成，可以方便地合成5-芳基取代的吡唑-3-基膦酸酯。这些吡唑是通过自发消除甲酰胺而在一锅中形成的。碱性条件阻止竞争性形成环丙基膦酸酯。3-芳基取代的吡唑-5-羧酸酯可以通过相同的方法由1-芳基乙烯基膦酸酯和重氮乙酸乙酯合成，尽管为了确保芳构化阶段成功且消除二乙氧基磷酰基部分是必需的，更强的碱NaH是必需的。
• Acid-induced reaction of aryldiazomethanes with olefins. Mechanism of reaction
  作者：G. L. Closs、S. H. Goh

  DOI：10.1021/jo00925a027

  日期：1974.6
• Mohammed; Gohar; Abdel-Latif, Pharmazie, 1985, vol. 40, # 5, p. 312 - 314
  作者：Mohammed、Gohar、Abdel-Latif、Badr

  DOI：——

  日期：——