2-chloropropionic acid diisopropylamide acid | 90477-06-8

• 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: 2-chloropropionic acid diisopropylamide acid
• 英文别名: 2-chloro-N,N-bis(propan-2-yl)propanamide；2-chloro-N,N-di(propan-2-yl)propanamide
• CAS: 90477-06-8
• 化学式: C₉H₁₈ClNO
• mdl: MFCD09388786
• 分子量: 191.701
• InChiKey: VMGBVCZLORGNTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloropropionic acid diisopropylamide acid 在 samarium diiodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 13.17h， 生成 (E)-N,N-Diisopropyl-2-methyl-3-phenylpropenamide
  参考文献：
  名称：

  Synthesis of (E)-α,β-Unsaturated Amides with High Selectivity by Using Samarium Diiodide

  摘要：

  Stereoselective beta -elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield alpha,beta -unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds a are easily prepared by reaction of the corresponding lithium enolates of alpha -chloroamides with aldehydes or ketones at -78 degreesC. The influence of the reaction conditions and the structure of the starting compounds on the stereoselectivity of the beta -elimination reaction is also discussed.

  DOI：

  10.1002/1521-3765(20010716)7:14<3062::aid-chem3062>3.0.co;2-f
• 作为产物：
  描述：

  2-氯丙酰氯 、 二异丙胺 生成 2-chloropropionic acid diisopropylamide acid
  参考文献：
  名称：

  由SmI 2促进的2,3-环氧酰胺的全部区域选择性和非对映特异性碘解：（2 R *，3 R *）-或（2 R *，3 S *）-2-羟基-3-碘酰胺的合成

  摘要：

  据报道，使用二碘化sa作为碘化物的来源。因此，通过用SmI 2处理其中环氧乙烷环为2，3-二取代或2，2，3-三取代的2，3-环氧酰胺，以总的区域选择性获得了2-羟基-3-碘酰胺。开环反应是非对映特异性的，并且分别从顺式或反式-环氧酰胺获得（2 R *，3 R *）-或（2 R *，3 S *）-2-羟基-3-碘酰胺。通过X射线分析确定2-羟基-3-碘酰胺的相对构型。已经提出了解释这种转变的机制。起始化合物1 通过在2-78°C下将2-氯酰胺衍生的烯醇化物与醛反应可轻松制备它们。

  DOI：

  10.1021/jo049021s

文献信息

• Manganese-Promoted Regioselective Ring-Opening of 2,3-Epoxy Acid Derivatives: A New Route to α-Hydroxy Acid Derivatives
  作者：José M. Concellón、Pablo L. Bernad、Humberto Rodríguez-Solla、Pamela Díaz

  DOI：10.1002/adsc.200900257

  日期：2009.9

  amides as starting materials, the corresponding 3-aryl-2-hydroxy amides in enantiopure form are also available. Some synthetic applications of selected examples of 3-aryl-2-hydroxy carboxylic acid derivatives are shown. A mechanism has been proposed to explain this novel reaction.

  描述了一种简单而通用的方法，该方法涉及由活性锰促进的从容易获得的2，3-环氧酰胺或酯合成3-芳基-2-羟基酰胺或具有总区域选择性的酯。利用对映纯的环氧酰胺作为起始原料，也可获得对映纯的相应的3-芳基-2-羟基酰胺。显示了3-芳基-2-羟基羧酸衍生物的选定实例的一些合成应用。已经提出了一种机制来解释这种新颖的反应。
• Synthesis of Aromatic (<i>E</i>)- or (<i>Z</i>)-α,β-Unsaturated Amides with Total or Very High Selectivity from α,β-Epoxyamides and Samarium Diiodide
  作者：José M. Concellón、Eva Bardales

  DOI：10.1021/jo0349577

  日期：2003.11.1

  stereoselective synthesis of aromatic alpha,beta-unsaturated amides was achieved by treatment of aromatic alpha,beta-epoxyamides with samarium diiodide. The starting compounds 1 and 3 are easily prepared by the reaction of enolates derived from alpha-chloroamides with carbonyl compounds at -78 degrees C. A mechanism to explain this transformation is proposed.

  通过用二碘化treatment处理芳香族α，β-环氧酰胺，可以高度立体选择性地合成芳香族α，β-不饱和酰胺。起始化合物1和3易于通过衍生自α-氯酰胺的烯醇化物与羰基化合物在-78℃下反应来制备。提出了解释这种转化的机理。
• Unusual reductive cleavage of 3-aryl-2,3-epoxyamides by using samarium diiodide. Synthesis of 3-aryl-3-deuterio-2-hydroxyamides with total regioselectivity
  作者：José M. Concellón、Eva Bardales、Cecilia Gómez

  DOI：10.1016/s0040-4039(03)01201-2

  日期：2003.7.7

  Ring-opening of 3-aryl-2,3-epoxyamides 1 was achieved by using samarium diiodide and D2O, yielding 3-aryl-3-deuterio-2-hydroxyamides 2 with total regioselectivity. The starting compounds 1 were easily prepared by reaction of the corresponding lithium or potassium enolates of α-chloroamides with aldehydes or ketones. When the reaction was carried out in the presence of H2O instead of D2O, the corresponding

  通过使用二碘化and和D 2 O实现3-芳基-2，3-环氧酰胺1的开环，得到具有总区域选择性的3-芳基-3-氘代-2-羟基酰胺2。通过使相应的α-氯酰胺的烯醇锂或钾的烯醇盐与醛或酮反应，可以容易地制备起始化合物1。当反应在H 2 O而不是D 2 O存在下进行时，分离出相应的3-芳基-2-羟基酰胺。对映体纯的3-芳基-2，3-环氧酰胺的处理提供了光学活性的3-芳基-2-羟基酰胺。
• Piperazine derivatives with anticholinergic and/or antihistaminic
  申请人：Selvi & C. S.p.A.

  公开号：US04457931A1

  公开（公告）日：1984-07-03

  Compounds of formula I ##STR1## are described in which R is an aryl, substituted aryl, aralkyl or heterocyclic radical; R.sup.1 is hydrogen or alkyl of 1-4 carbon atoms; A is a saturated, aliphatic hydrocarbon chain, which is linear or branched; R.sup.2 and R.sup.3 are the same or different and are hydrogen, linear or branched alkyl, aryl, substituted aryl or together with the nitrogen atom to which they are connected and together with y form a ring wherein y is a methylene group or a heteroatom, which is selected from the group consisting of nitrogen, oxygen and sulfur; R.sup.4 is hydrogen or linear or branched alkyl; X is halogen or an organic or inorganic anion; n is 0; 1; 2; 3 or in the case of a bifunctional acid, n is equal to 0.5; 1.5; 2.5 and their enantiomers and diestereoisomers. Several methods of preparation of the novel compounds are described.

  该文描述了式子I的化合物，其中R是芳基，取代芳基，芳基烷基或杂环基；R.sup.1是氢或1-4个碳原子的烷基；A是饱和的，直链或支链的脂肪烃链；R.sup.2和R.sup.3相同或不同，是氢、直链或支链烷基、芳基、取代芳基或与它们连接的氮原子一起形成环，其中y是亚甲基或杂原子，所述杂原子选自氮、氧和硫的群；R.sup.4是氢或直链或支链烷基；X是卤素或有机或无机阴离子；n为0、1、2、3，或在双官能酸的情况下，n等于0.5、1.5、2.5以及它们的对映异构体。文中还描述了几种制备这些新化合物的方法。
• Sequential Elimination−Cyclopropanation Reactions Promoted by Samarium:  Highly Diastereoselective Synthesis of Cyclopropylamides
  作者：José M. Concellón、Humberto Rodríguez-Solla、Ricardo Llavona

  DOI：10.1021/jo0262098

  日期：2003.2.1

  trans-Cyclopropanamides were obtained, in high yield, from 2-chloro-3-hydroxyamides by a sequenced elimination-cyclopropanation process promoted by Samarium/diiodomethane or Samarium diiodide and Samarium/diiodomethane.