4-氯-2-丁炔酸甲酯 | 41658-12-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-氯-2-丁炔酸甲酯
• 英文名称: methyl 4-chloro-2-butynoate
• 英文别名: Chlortetrolsaeuremethylester；methyl chlorotetrolate；Methyl 4-chlorobut-2-ynoate
• CAS: 41658-12-2
• 化学式: C₅H₅ClO₂
• mdl: MFCD19232073
• 分子量: 132.546
• InChiKey: SQWTVWVBVHSZGM-UHFFFAOYSA-N

物化性质

• 沸点：
  75.5 °C(Press: 11 Torr)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  4-氯-2-丁炔酸甲酯 在 Sodium tetraborate decahydrate 、 potassium dihydrogenphosphate 、 sodium azide 作用下， 以 水 为溶剂， 反应 0.5h， 以79%的产率得到methyl (Z)-3-azido-4-chloro-2-butenoate
  参考文献：
  名称：

  Priebe, Hanno, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, # 9, p. 640 - 645

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯丙炔 、 氯甲酸甲酯 在 甲基锂 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以60%的产率得到4-氯-2-丁炔酸甲酯
  参考文献：
  名称：

  一种简单高效的氯四乙酸酯的合成

  摘要：

  与先前报道的这些生物化学试剂的三步低产率合成相反，用甲基锂和过量的氯甲酸烷基酯处理炔丙基氯可得到平均含量为65％的氯代四乙酸酯。

  DOI：

  10.1039/c39820001290

文献信息

• Streamlined Access to Functionalized Chromenes and Quinolines using Domino Reactions of Salicylic Aldehydes and Methyl 4-Chloro-2-butynoate
  作者：Davide Bello、Javier Ruiz-Rodríguez、Fernando Albericio、Rosario Ramón、Rodolfo Lavilla

  DOI：10.1002/ejoc.201000559

  日期：——

  Methyl 4-chloro-2-butynoate was used in a modified Morita-Baylis―Hillman reaction with salicylic aldehydes. The chlorine atom in the alkynoate moiety allows its efficient isomerization to the corresponding allene, and remains in the adduct as a reactive site. Further one-pot derivatization leads to a variety of substituted chromenes and quinolines.

  4-氯-2-丁酸甲酯用于改进的 Morita-Baylis-Hillman 反应与水杨醛。炔酸酯部分中的氯原子允许其有效异构化为相应的丙二烯，并作为反应位点保留在加合物中。进一步的一锅衍生产生多种取代的色烯和喹啉。
• Heterocyclic compound studies. II. Synthesis of 1,4-benzodioxin, 1,4-benzoxathiin, 1,4-benzoxazine and 1,4-benzothiazine derivatives
  作者：Salvatore Cabiddu、Costantino Floris、Stefana Melis、Francesca Sotgiu、Giovanni Cerioni

  DOI：10.1002/jhet.5570230642

  日期：1986.11

  Benzocondensed six-membered heterocyclic rings containing two heteroatoms have been synthesized by a generally applicable method starting from disubstituted benzene compounds and methyl 4-chlorobutynoate (1) or methyl 4-bromobutenoate (2). The reactions with 1 yield a mixture of endo and exo (E or Z) isomers. The 13C nmr spectroscopy was used to assign the structure of the synthesized compounds.

  已经通过通常适用的方法从二取代的苯化合物和4-氯丁酸甲酯（1）或4-溴丁烯酸甲酯（2）开始合成了包含两个杂原子的苯并稠合的六元杂环。与1的反应产生内和外（E或Z）异构体的混合物。的13 C NMR光谱法用于分配合成的化合物的结构。
• Convenient Syntheses of Methyl 2-Bromo- and 2-Iodo-2,3-butadienoates
  作者：Thomas Gillmann、Stefan Heckhoff、Thomas Weeber

  DOI：10.1080/00397919408010226

  日期：1994.8

  Abstract Syntheses of methyl 2-bromo- and 2-iodo-2,3-butadienoates 3 and 6 from readily available starting materials are described. 3 and 6 will be valuable building blocks for the synthesis of 2-aryl and 2-alkenyl substituted alka-2,3-dienoates via Palladium-catalyzed cross-coupling reactions.

  摘要描述了从容易获得的起始材料合成 2-溴-和 2-碘-2,3-丁二烯酸甲酯 3 和 6。图 3 和 6 将是通过钯催化的交叉偶联反应合成 2-芳基和 2-烯基取代的 2,3-二烯酸烷基酯的有价值的构建单元。
• Process for the synthesis of 6-chloromethyluracil
  申请人：Procos S.P.A.

  公开号：US11028057B2

  公开（公告）日：2021-06-08

  The invention relates to a process for the synthesis of 6-chloromethyluracil (6-(chloromethyl)pyrimidin-2,4(1H,3H)-dione) from ethyl 4-chloroacetoacetate and S-methylisothiourea hemisulfate via isolation of the novel intermediate 6-(chloromethyl)-6-hydroxy-2-(methylthio)-5,6-dihydropyrimidin-4(1H)-one, and its subsequent treatment with aqueous sulfuric acid. Formula (I).

  本发明涉及一种合成 6-氯甲基尿嘧啶（6-(氯甲基)嘧啶-2,4(1H. 3H)-二酮）的工艺、3H)-二酮)的工艺，该工艺通过分离新型中间体 6-(氯甲基)-6-羟基-2-(甲硫基)-5,6-二氢嘧啶-4(1H)-酮，然后用硫酸水溶液处理，从 4-氯乙酰乙酸乙酯和 S-甲基异硫脲半硫酸盐中合成。式 (I).
• Reaction of nucleic acid bases with .alpha.-acetylenic esters. 5. Synthesis and properties of adenosine and cytidine derivatives
  作者：Pierre Roques、Jean Yves Le Gall、Liliane Lacombe、Martin Olomucki

  DOI：10.1021/jo00031a045

  日期：1992.2

  Alpha-Acetylenic esters are able to react under mild experimental conditions with the base moiety of adenosine and cytidine, while guanosine is unreactive. A double reaction of the triple bond and the ester group of the reagent with the NH2 group and the adjacent ring nitrogen of the base yields derivatives in which an additional pyrimidone ring is fused to the original base. These derivatives can exist in two isomeric forms. In alkaline solution, or by prolonged heating in water, the medium pyrimidine ring of adenosine derivatives opens by loss of carbon 5. If the derivatization is performed with chlorotetrolic (4-chloro-2-butynoic) acid esters, the modified nucleobases contain a chloromethyl side chain. Tests of the alkylating abilities of the latter in the two isomeric adenosine derivatives show that the chlorine can be easily substituted by a thiol in the presence of alkali; a partial Dimroth rearrangement of one of the reaction products is observed. The reaction with amines is accompanied by ring opening. Nucleic acids containing these alkylating base derivatives can be cross-linked to other macromolecules such as solid supports or contact proteins.