氯甲基丁-2-烯酸酯 | 27550-74-9

• 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: 氯甲基丁-2-烯酸酯
• 英文名称: chloromethyl crotonate
• 英文别名: Chlormethylcrotonat；Chloromethyl but-2-enoate
• CAS: 27550-74-9
• 化学式: C₅H₇ClO₂
• mdl: MFCD19233642
• 分子量: 134.562
• InChiKey: PYOXKUJLQNOEIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  3
• 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

反应信息

• 作为反应物：
  描述：

  氯甲基丁-2-烯酸酯 在 sodium iodide 、 锌 作用下， 以 丙酮 为溶剂， 反应 11.08h， 生成 (E)-2-oxo-2-phenylethyl but-2-enoate
  参考文献：
  名称：

  Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen

  摘要：

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.

  DOI：

  10.1021/jo00055a010
• 作为产物：
  描述：

  聚合甲醛 、 巴豆酰氯 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以34%的产率得到氯甲基丁-2-烯酸酯
  参考文献：
  名称：

  Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen

  摘要：

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.

  DOI：

  10.1021/jo00055a010

文献信息

• Biphenylylpropionic acid derivative, process for preparing the same and pharmaceutical composition containing the same
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：EP0103265A2

  公开（公告）日：1984-03-21

  Biphenylylpropionic acid derivatives of the formula: wherein R is an alkylcarbonyloxyalkyl group or an alkenylcarbonyloxyalkyl group having the formula: wherein R1 is hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms, R2 is an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and m is 0 or an integer of 1, provided that when R1 is a lower alkyl group, m is 0, or a lactone having the formula: wherein R3 and R4 are hydrogen atom or a lower alkyl group having 1 to 2 carbon atoms, and n is an integer of 1 or 2. The compounds have excellent anti-inflammatory, analgesic and antipyretic activities. Moreover, the compounds have no irritation, rapid and long acting and high safety margin.

  公式如下的双苯基丙酸衍生物： 其中R是具有以下式子的烷基羧酸氧烷基或烯基羧酸氧烷基： 其中R1是氢原子或具有1到5个碳原子的低烷基，R2是具有1到15个碳原子的烷基或具有2到8个碳原子的烯基，m为0或1的整数，但当R1为低烷基时，m为0，或具有以下式子的内酯： 其中R3和R4是氢原子或具有1到2个碳原子的低烷基，n为1或2的整数。这些化合物具有出色的抗炎、镇痛和退烧活性。此外，这些化合物无刺激性，作用迅速且持久，安全性高。
• Ester derivative of substituted acetic acid and preparing the same
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：EP0132814B1

  公开（公告）日：1988-12-21
• US4603217A
  申请人：——

  公开号：US4603217A

  公开（公告）日：1986-07-29
• US4699925A
  申请人：——

  公开号：US4699925A

  公开（公告）日：1987-10-13