(E)-1-isopropyl-3-nitro-2-propenyl acetate | 132839-67-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (E)-1-isopropyl-3-nitro-2-propenyl acetate
• 英文别名: 1-isopropyl-3-nitro-2-propenyl acetate；[(E)-4-methyl-1-nitropent-1-en-3-yl] acetate
• CAS: 132839-67-9
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: GQCMWALUBAFBJZ-SNAWJCMRSA-N

物化性质

• 沸点：
  279.7±23.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-bromo-2-methylpropyl acetate 、 (E)-1-硝基-2-(苯基磺酰基)乙烯 生成 (E)-1-isopropyl-3-nitro-2-propenyl acetate
  参考文献：
  名称：

  Preparation of polyfunctional nitro olefins and nitroalkanes using the copper-zinc reagents RCu(CN)ZnI

  摘要：

  The addition of the copper-zinc reagents RCu(CN)ZnX to a variety of nitro olefins produces polyfunctional nitroalkanes in high yields. The intermediate zinc or copper nitronates can be directly submitted to a Nef reaction (O3,-78-degrees-C) and converted to polyfunctional ketones in a one-pot procedure. The addition of RCu(CN)ZnX to nitro olefins bearing a leaving group (RSO2, RS) in the beta-position provides pure (E)-nitro olefins in excellent yields. The reaction has been applied for the stereoselective preparation of 1,3-nitrodienes and for a Diels-Alder reaction precursor.

  DOI：

  10.1021/jo00046a027

文献信息

• Highly stereoselective preparation of nitro olefins and nitro dienes by the addition-elimination of copper-zinc organometallics to β-alkylthio and β-phenylsulfonyl nitro olefins
  作者：Carole Retherford、Paul Knochel

  DOI：10.1016/s0040-4039(00)79462-7

  日期：1991.1

  onyl ethylene 2a gave highly functionalized pure (E) nitro olefins and stereoselectively (1E, 3E) and (1E, 3Z)-1-nitrodienes in excellent yields. β-Alkylthio nitro olefins such as 2-ethylthio-1-nitro-1-cyclohexene 2b and 2,2-dimethylthio-1-nitroethylene 12 were found to have a similar behavior. This methodology allowed an expeditive preparation of the triene 5 which underwent an extremely mild silica

  将铜锌有机金属RCu（CN）ZnX加成消除至（E）-1-硝基-2-苯基磺酰基乙烯2a，得到高度官能化的纯（E）硝基烯烃，并立体选择性地（1E，3E）和（1E，3Z） -1-硝基二烯的收率极高。发现β-烷硫基硝基烯烃如2-乙基硫基-1-硝基-1-环己烯2b和2，2-二甲基硫基-1-硝基乙烯12具有相似的行为。该方法学允许快速地制备三烯5，该三烯5经历了极其温和的硅胶催化的立体定向Diels-Alder环化。
• 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：——