N-(3-carbethoxy-3-butenyl)phthalimide | 24249-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(3-carbethoxy-3-butenyl)phthalimide
• 英文别名: ethyl 4-(1,3-dioxoisoindolin-2-yl)-2-methylenebutanoate；Ethyl-α-methylen-γ-phthalimido-butyrat；Ethyl 4-(1,3-dioxoisoindol-2-yl)-2-methylidenebutanoate
• CAS: 24249-90-9
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: SVPNPLUXKXDAOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴甲基丙烯酸乙酯 在 三甲基氯硅烷 、 sodium hydride 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 N-(3-carbethoxy-3-butenyl)phthalimide
  参考文献：
  名称：

  Ethyl-2-(2-chloroethyl)acrylate: a new very versatile α-cyclopropylester cation synthon. Efficient synthesis of cyclopropane ester derivatives by Michael addition-induced cyclization reaction

  摘要：

  We report here the use of the readily accessible ethyl-2-(2-chloroethyl)acrylate as a new very versatile alpha-cyclopropylester cation synthon, which reacts efficiently and selectively with carbon-, nitrogen-, sulfur- or phosphorus-centered nucleophiles through Michael addition followed by intramolecular capture of the incipient ester enolate to afford funtionalized cyclopropane esters in high yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.046

文献信息

• Addition of<i>N</i>-(Hydroxymethyl)phthalimide to Methacrylates by Carbon–Carbon Bond Formation
  作者：Keisuke Kurita、Hiroshi Itoh、Shunji Chikamori、Tomoyuki Mabuchi

  DOI：10.1246/bcsj.61.3755

  日期：1988.10

  N-(Hydroxymethyl)phthalimide undergoes addition to the carbon–carbon bond of methacrylates effectively in sulfuric acid, resulting in the formation of a new carbon–carbon bond.

  N-(羟甲基)苯二酰亚胺在硫酸中有效地与甲基丙烯酸酯的碳－碳键发生加成反应，导致新碳－碳键的形成。
• Silver-Catalyzed Decarboxylative Allylation of Aliphatic Carboxylic Acids in Aqueous Solution
  作者：Lei Cui、He Chen、Chao Liu、Chaozhong Li

  DOI：10.1021/acs.orglett.6b00802

  日期：2016.5.6

  Direct decarboxylative radical allylation of aliphatic carboxylic acids is described. With K2S2O8 as the oxidant and AgNO3 as the catalyst, the reactions of aliphatic carboxylic acids with allyl sulfones in aqueous CH3CN solution gave the corresponding alkenes in satisfactory yields under mild conditions. This site-specific allylation method is applicable to all primary, secondary, and tertiary alkyl

  描述了脂肪族羧酸的直接脱羧自由基烯丙基化。以K 2 S 2 O 8为氧化剂，AgNO 3为催化剂，脂肪族羧酸与烯丙基砜在CH 3 CN水溶液中的反应在温和条件下以令人满意的收率得到了相应的烯烃。此位点特定的烯丙基化方法适用于所有伯，仲和叔烷基酸，并具有广泛的官能团相容性。
• Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen
  作者：Paul Knochel、Tso Sheng Chou、Carole Jubert、Duddu Rajagopal

  DOI：10.1021/jo00055a010

  日期：1993.1

  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.
• Knochel Paul, Chou Tso-Sheng, Jubert Carole, Rajagopal Duddu, J. Org. Chem., 58 (1993) N 3, S 588-599
  作者：Knochel Paul, Chou Tso-Sheng, Jubert Carole, Rajagopal Duddu

  DOI：——

  日期：——
• Ethyl-2-(2-chloroethyl)acrylate: a new very versatile α-cyclopropylester cation synthon. Efficient synthesis of cyclopropane ester derivatives by Michael addition-induced cyclization reaction
  作者：Mathilde Lachia、Sébastien Iriart、Myriam Baalouch、Alain De Mesmaeker、Renaud Beaudegnies

  DOI：10.1016/j.tetlet.2011.04.046

  日期：2011.6

  We report here the use of the readily accessible ethyl-2-(2-chloroethyl)acrylate as a new very versatile alpha-cyclopropylester cation synthon, which reacts efficiently and selectively with carbon-, nitrogen-, sulfur- or phosphorus-centered nucleophiles through Michael addition followed by intramolecular capture of the incipient ester enolate to afford funtionalized cyclopropane esters in high yields. (C) 2011 Elsevier Ltd. All rights reserved.