trans-2-phenyl-3-nitrocyclopropane-1,1-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-2-phenyl-3-nitrocyclopropane-1,1-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 2-nitro-3-phenylcyclopropane-1,1-dicarboxylate；dimethyl trans-2-nitro-3-phenylcyclopropane-1,1-dicarboxylate；dimethyl (2R,3S)-2-nitro-3-phenylcyclopropane-1,1-dicarboxylate
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: IYKQWMXDSAGDGX-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-2-phenyl-3-nitrocyclopropane-1,1-dicarboxylic acid dimethyl ester 在 盐酸 、 锌 作用下， 以 水 为溶剂， 以52%的产率得到β-aminocyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  硝基烯烃与活化亚甲基化合物的迈克尔加成反应的氧化环化反应可高效立体选择性合成硝基环丙烷

  摘要：

  据报道，通过二碘代苯二乙酸酯和碘化四丁铵的结合，硝基烯烃的迈克尔加成物与活化的亚甲基化合物的有效氧化环丙烷化反应。在温和条件下，通过迈克尔加成和环丙烷化，以高非对映选择性和对映选择性，以中等至良好的产率合成了高度官能化的硝基环丙烷。

  DOI：

  10.1002/adsc.200800452
• 作为产物：
  描述：

  α-Carbomethoxy-α-brom-β-phenyl-γ-nitro-buttersaeuremethylester 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 trans-2-phenyl-3-nitrocyclopropane-1,1-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of functionalised cyclopropanes from nitroalkenes via an organocatalysed Michael-initiated ring-closure approach

  摘要：

  Synthetically useful nitrocyclopropanes are easily obtained via Michael addition of dimethyl bromomalonate to nitrostyrenes promoted by commercially available (S)-alpha,alpha-di-beta-naphthlyl-2-pyrrolidinemethanol as the catalyst, followed by DABCO-mediated intramolecular nucleophilic substitution. The functionalised nitrocyclopropanes are obtained in good yield, excellent diastereoselectivity and up to 49% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.005

文献信息

• Divergent Reactivity of Nitrocyclopropanes with Huisgen Zwitterions and Facile Syntheses of 3-Alkoxy Pyrazolines and Pyrazoles
  作者：Changjiang Yang、Wei Liu、Zijian He、Zhengjie He

  DOI：10.1021/acs.orglett.6b02415

  日期：2016.10.7

  A novel annulation reaction of trans-2-substituted-3-nitrocyclopropane-1,1-carboxylates with in situ generated Huisgen zwitterions is reported, providing facile synthesis of 3-alkoxy pyrazolines in good yields and high diastereoselectivities. This reaction unveils the divergent reactivity of the nitrocyclopropanes as a kind of versatile donor–acceptor cyclopropanes. It is also demonstrated that the

  报道了一种新的反式-2-取代-3-硝基环丙烷-1,1-羧酸盐与原位产生的惠斯根两性离子的环化反应，可轻松合成3-烷氧基吡唑啉，产率高且非对映选择性高。该反应揭示了硝基环丙烷作为一种多功能的供体-受体环丙烷具有不同的反应性。还证明了由偶氮二羧酸二叔丁酯制备的3-烷氧基吡唑啉可以容易地以中等收率转化成相应的3-烷氧基1 H-吡唑。
• Iodobenzene-Catalyzed Oxidative Cyclization for the Synthesis of Highly Functionalized Cyclopropanes
  作者：Yang Li、Hao Guo、Renhua Fan

  DOI：10.1055/s-0039-1690809

  日期：2020.3

  iodobenzene-catalyzed oxidative cyclization of Michael adducts of activated methylene compounds with nitroolefins or chalcones is developed. mCPBA is used as oxidant together with Bu4NI for the generation of a highly reactive iodine(III) species to mediate the cyclopropanation via a ligand exchange and reductive elimination process. A range of highly functionalized cyclopropanes are synthesized with

  开发了碘代苯催化的活化亚甲基化合物的迈克尔加合物与硝基烯烃或查耳酮的氧化环化反应。m CPBA与Bu 4 NI一起用作氧化剂，用于生成高反应性碘（III）物种，以通过配体交换和还原消除过程介导环丙烷化。合成具有高非对映选择性的一系列高度官能化的环丙烷。
• Stereoselective Synthesis of Highly Functionalized Nitrocyclopropanes via Organocatalyic Conjugate Addition to Nitroalkenes
  作者：Séamus H. McCooey、Thomas McCabe、Stephen J. Connon

  DOI：10.1021/jo0613838

  日期：2006.9.1

  A convenient and novel one-pot organocatalytic methodology for the stereoselective synthesis of highly functionalized nitrocyclopropanes is reported. The addition of dimethyl chloromalonate to a variety of nitroolefins catalyzed by tertiary amines leads to a Michael adduct which cyclizes to form the cyclopropane in the presence of DBU under carefully controlled reaction conditions with outstanding

  报道了一种方便且新颖的一锅法有机催化方法，用于立体选择性合成高度官能化的硝基环丙烷。将氯丙二酸二甲酯添加到由叔胺催化的各种硝基烯烃中会导致迈克尔加成物，该加成物在DBU存在下，在精心控制的反应条件下，以非对映选择性优异地环化形成环丙烷。
• Highly Enantioselective Synthesis of Nitrocyclopropanes via Organocatalytic Conjugate Addition of Bromomalonate to α,β-Unsaturated Nitroalkenes
  作者：Yi-ning Xuan、Shao-zhen Nie、Li-ting Dong、Jun-min Zhang、Ming Yan

  DOI：10.1021/ol900227j

  日期：2009.4.2

  Highly enantioselective synthesis of nitrocyclopropanes was achieved via the organocatalytic conjugate addition of dimethyl bromomalonate to nitroalkenes and the consequent intramolecular cyclopropanation. 6′-Demethyl quinine was found to be the efficient catalyst. Excellent enantioselectivities, diastereoselectivities, and good yields were obtained for a variety of aryl or heteroaryl nitroethylenes

  硝基环丙烷的高度对映选择性合成是通过将溴代丙二酸二甲酯向硝基烯烃的有机催化共轭加成反应以及随后的分子内环丙烷化而实现的。发现6'-脱甲基奎宁是有效的催化剂。对于各种芳基或杂芳基硝基乙烯，获得了优异的对映选择性，非对映选择性和良好的收率。
• Sopova,A.S. et al., Journal of Organic Chemistry USSR (English Translation), 1975, vol. 11, p. 65 - 68
  作者：Sopova,A.S. et al.

  DOI：——

  日期：——