methyl-trans-3-chloroacrylate | 5135-18-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl-trans-3-chloroacrylate
• 英文别名: (2E)-3-Chlor-prop-2-ensaeure-methylester；trans-3-chloroacrylic acid methyl ester；methyl trans-β-chloroacrylate；methyl (E)-3-chloroprop-2-enoate；methyl trans-3-chloro-propenoate；methyl trans-3-chloropropenoate
• CAS: 5135-18-2
• 化学式: C₄H₅ClO₂
• 分子量: 120.535
• InChiKey: ZLDNFLVIPPOXQL-NSCUHMNNSA-N

物化性质

• 沸点：
  124.1±13.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)
• 保留指数：
  748;766.5;748;766

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl-trans-3-chloroacrylate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 生成 (E)-β-(methoxycarbonyl)vinyl azide
  参考文献：
  名称：

  Syntheses and properties of 5-substituted [n](2,4)pyridinophanes, model compounds of NAD(P)

  摘要：

  [n](2,4)Pyridinophane derivatives 5-8 having an ester or an amide group at the 5-position were synthesized by aza-Wittig reactions between beta-substituted vinyliminophosphoranes and cyclic alpha,beta-unsaturated ketones. [beta-(Methoxycarbonyl)vinyl]- (1), [beta-(N,N-tetramethylenecarbamoyl)vinyl]-(2), [beta-(N-benzylcarbamoyl)vinyl]-(3), and (beta-carbamoylvinyl)iminophosphorane (4) were synthesized from the corresponding vinyl azides and triphenylphosphine. The heptamethylene chains of 5-(methoxycarbonyl)[7](2,4)pyridinophane (5),5-(N,N-tetramethylenecarbamoyl)[7](2,4)pyridinophane (6), and 5-(N-benzylcarbamoyl)[7](2,4)pyridinophane (7) flipped with AG(double dagger) = 11.2 (T(c) = 10.3-degrees-C), 10.8 (T(c) = 0.2-degrees-C), and 10.5 kcal/mol (T(c) = -5.2-degrees-C), respectively. At lower temperatures, the three conformations of the heptamethylene bridge were frozen. Methylpyridinium iodides 10 (n = 7, 6, and 5) derived from 6 were reduced more easily [E1/2* (half height potential) = -1.65 V (n = 7); -1.63 V (n = 6); -1.29 V vs Ag/AgCl (n = 5)] than the reference compound, 2,4-diethyl-5-(N,N-tetramethylenecarbamoyl)pyridinium ion (11) [E1/2* = -1.82 V vs Ag/AgCl]. The reduced species dimerized quickly.

  DOI：

  10.1021/jo00060a018
• 作为产物：
  描述：

  丙炔酸甲酯 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 methyl-trans-3-chloroacrylate 、 methyl cis-2-chloroacrylate
  参考文献：
  名称：

  Heasley, Victor L.; Elliott, Stephen L.; Erdman, Paul E., Journal of the Chemical Society. Perkin transactions II, 1991, # 3, p. 393 - 399

  摘要：

  DOI：

文献信息

• Total synthesis of the polyene macrolide antibiotic roxaticin. II. Total synthesis of roxaticin
  作者：Yuji Mori、Motoya Asai、Jun-ichiro Kawade、Hiroshi Furukawa

  DOI：10.1016/0040-4020(95)00215-t

  日期：1995.5

  Roxaticin has been synthesized in a convergent manner from the polyol segment 2, which was prepared by the Julia coupling reaction of sulfone 4 and aldehyde 8, and the polyene phosphonate 3. The cyclization was achieved by macrolactonization.

  罗沙汀是由多元醇链段2聚合合成的，多元醇链段2是通过砜4和醛8的朱莉娅偶联反应和多烯膦酸酯3制备的。通过大内酯化实现环化。
• Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04281127A1

  公开（公告）日：1981-07-28

  Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid derivatives of the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, lower cycloalkyl, lower alkoxy, hydroxy, halo, lower alkykthio, lower alkylsulfinyl, lower alkylsulfonyl, di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n O-- or 2-hydroxyethoxy; R.sub.2 is hydrogen, lower alkyl or lower alkoxy; R.sub.3 is hydroxy, lower alkoxy, di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n O-- or di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n NH--; and n is 2 to 7; provided that at least one of R.sub.1 and R.sub.2 is other than hydrogen, when R.sub.3 is hydroxy, a salt thereof with a pharmaceutically acceptable base, or when R.sub.3 is di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n O-- or di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n NH--, a salt thereof with a pharmaceutically acceptable acid, and a process for the preparation thereof, are described. The compounds of formula I are useful as agents in the prevention of allergic reactions.

  公式为##STR1##的Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid衍生物，其中R.sub.1为氢、较低烷基、较低环烷基、较低烷氧基、羟基、卤素、较低烷硫基、较低烷基磺基、较低烷基砜基、二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n O--或2-羟基乙氧基；R.sub.2为氢、较低烷基或较低烷氧基；R.sub.3为羟基、较低烷氧基、二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n O--或二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n NH--；n为2至7；要求至少R.sub.1和R.sub.2中的一个不是氢，当R.sub.3为羟基时，其与药用可接受的碱的盐，或当R.sub.3为二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n O--或二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n NH--时，其与药用可接受的酸的盐，以及其制备方法。公式I的化合物可用作预防过敏反应的药物。
• Methodology for the polyene and related antibiotics-versatile and practical access to bifunctional all-trans polyolefinic systems
  作者：Stephen Hanessian、Maurizio Botta

  DOI：10.1016/s0040-4039(00)95312-7

  日期：1987.1

  A method is described to assemble all-trans bifunctional polyolefinic chains based on the reaction of aldehydes with a trienic phosphorane developed by Vedejs and coworkers.

  描述了一种基于醛与Vedejs和同事开发的三烯磷烷的反应组装全反式双官能聚烯烃链的方法。
• Halogenation of unsaturated esters—II
  作者：Maija Pitkänen、Ilpo O.O. Korhonen

  DOI：10.1016/s0040-4020(01)91588-1

  日期：1983.1

  The addition of chlorine, bromine chloride and bromine to methyl 2-chloropropenoate 1, methyl cis - 3 - chloropropenoate 2 and methyl trans - 3 - chloropropenoate 3 under ionic and radical conditions gave regioisomer mixtures. Both trans- and cis-addition of halogen species was observed, bromine preferentially adding to the non-halogenated carbon atom.

  在离子和自由基条件下，将氯，溴化氯和溴加到2-氯丙酸甲酯1，顺式3-氯丙酸甲酯2和反式-3-氯丙酸甲酯3中，得到区域异构体混合物。两个反式-和CIS观察卤素物质的-addition，溴优先增加了非卤化碳原子。
• Reaction of activated vinyl halides with tervalent phosphorus nucleophiles
  作者：Gerald Pattenden、Brian J. Walker

  DOI：10.1039/j39690000531

  日期：——

  cis- and trans- Isomers of derivatives of 3-halogenoacrylic acids undergo nucleophilic displacement reactions with triphenylphosphine, tri-n-butylphosphine, and triethyl phosphite to produce the correspondingtrans-vinyl-phosphonium salts and -phosphonates exclusively. 1H n.m.r.spectra are reported for these compounds. The mechanism of the displacement reaction is discussed.

  3-卤代丙烯酸衍生物的顺式和反式异构体与三苯基膦，三正丁基膦和亚磷酸三乙酯进行亲核取代反应，仅生成相应的反式-乙烯基-盐和-膦酸酯。据报道这些化合物的1 H nmr光谱。讨论了置换反应的机理。