(E)-4,4-dimethyl-2-nitro-2-pentene

• 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)-4,4-dimethyl-2-nitro-2-pentene
• 英文别名: (E)-4,4-dimethyl-2-nitropent-2-ene
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: YSDSOZGAMKZUCY-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4,4-dimethyl-2-nitro-2-pentene 在 baker's yeast 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以57%的产率得到4,4-dimethyl-2-nitropentane
  参考文献：
  名称：

  Asymmetric reduction of nitroalkenes with baker's yeast

  摘要：

  Various alpha,beta -disubstituted and trisubstituted nitroalkenes were chemoselectively reduced with baker's yeast to the corresponding nitroalkanes. Stereoselectivities of the reduction of alpha,beta -disubstituted nitroalkenes were modest to low, and e.e.s up to 52% were obtained. Trisubstituted nitroalkenes could be reduced to the corresponding nitroalkanes with excellent enantioselectivities, moderate diastereoselectivities and in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00029-5
• 作为产物：
  描述：

  硝基乙烷 、 特戊醛 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以79%的产率得到(E)-4,4-dimethyl-2-nitro-2-pentene
  参考文献：
  名称：

  （E）-或（Z）-硝基烯烃的简便且高度立体选择性的一锅合成。

  摘要：

  在催化量的哌啶存在下，脂族醛与硝基烷烃在4 A分子筛上反应。只需通过改变反应条件（溶剂和温度），就可以控制反应的立体化学结果，从而以高到极好的收率获得纯的（E）-和（Z）-硝基烯烃。除哌啶外，分子筛在立体化学控制中的作用似乎至关重要，特别是对于Z异构体的合成而言。

  DOI：

  10.1021/ol800224k

文献信息

• Insights into the diastereoselective control in the sulfa-Michael addition of thiols to nitroalkenes: stereoelectronic effect in the cyclic chelated transition state
  作者：Jiandong Wang、Pingfan Li、Zhanhui Yang、Ning Chen、Jiaxi Xu

  DOI：10.1016/j.tet.2015.11.030

  日期：2016.1

  two approximately 1,2-diaxial substituents due to stereoelectronic effect control. The stereoelectronic effect in the cyclic chelated transition state was probed and verified by tuning the steric bulkiness of the corresponding substituents. The reaction involving 1-nitrocyclohexene provided perfect support for the proposed diastereoselective control model. The current investigation provided not only

  研究了磺胺-迈克尔加成硝基烯烃和硫醇锂后进行质子化的非对映选择性控制。首先将硫醇锂添加到硝基烯烃中，得到环状的锂螯合的硝酸盐。由于具有立体电子效应，通过螯合物控制的六元半椅过渡态带有两个大约1,2-双轴取代基，证明了随后的硝酸盐动力学质子化是立体化学决定因素。通过调节相应取代基的空间体积，探索并验证了在环状螯合过渡态下的立体电子效应。涉及1-硝基环己烯的反应为提出的非对映选择性控制模型提供了完美的支持。
• Asymmetric reduction of nitroalkenes with baker's yeast
  作者：Yasushi Kawai、Yoshikazu Inaba、Norihiro Tokitoh

  DOI：10.1016/s0957-4166(01)00029-5

  日期：2001.2

  Various alpha,beta -disubstituted and trisubstituted nitroalkenes were chemoselectively reduced with baker's yeast to the corresponding nitroalkanes. Stereoselectivities of the reduction of alpha,beta -disubstituted nitroalkenes were modest to low, and e.e.s up to 52% were obtained. Trisubstituted nitroalkenes could be reduced to the corresponding nitroalkanes with excellent enantioselectivities, moderate diastereoselectivities and in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Facile and Highly Stereoselective One-Pot Synthesis of Either (<i>E</i>)- or (<i>Z</i>)-Nitro Alkenes
  作者：Stefania Fioravanti、Lucio Pellacani、Paolo A. Tardella、Maria Cecilia Vergari

  DOI：10.1021/ol800224k

  日期：2008.4.1

  of catalytic amounts of piperidine over 4 A molecular sieves. Simply by changing reaction conditions (solvent and temperature) it is possible to control the stereochemical outcome of the reactions, obtaining pure (E)- and (Z)-nitro alkenes in high to excellent yields. The role of molecular sieves on the stereochemical control seems crucial in addition to that of piperidine, especially for the synthesis

  在催化量的哌啶存在下，脂族醛与硝基烷烃在4 A分子筛上反应。只需通过改变反应条件（溶剂和温度），就可以控制反应的立体化学结果，从而以高到极好的收率获得纯的（E）-和（Z）-硝基烯烃。除哌啶外，分子筛在立体化学控制中的作用似乎至关重要，特别是对于Z异构体的合成而言。