1-Phenyl-2-nitro-3.3-dicarboaethoxy-cyclopropan | 22975-26-4

• 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: 1-Phenyl-2-nitro-3.3-dicarboaethoxy-cyclopropan
• 英文别名: diethyl 2-nitro-3-phenylcyclopropane-1,1-dicarboxylate
• CAS: 22975-26-4
• 化学式: C₁₅H₁₇NO₆
• 分子量: 307.303
• InChiKey: HWBUCTKVQPLMNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  1-Phenyl-2-nitro-3.3-dicarboaethoxy-cyclopropan 在 caesium carbonate 作用下， 以 水 为溶剂， 反应 4.0h， 以82.8%的产率得到(E)-2-benzylidene-5-phenylpent-4-yne-1,1,3,3-tetracarboxylate
  参考文献：
  名称：

  从硝基环丙烷原位生成高反应性丙二烯：烯炔和烯酯的可控合成

  摘要：

  首次开发了一种新的有效的硝基环丙烷开环反应策略，用于通过原位生成的高反应性缺电子中间体丙二烯来发散合成烯炔和烯酯。可控方法导致烯炔和烯酯的产率分别高达 89% 和 90%。该反应操作简单，涉及绿色溶剂和简单的无机碱，不含过渡金属。

  DOI：

  10.1039/d1cc01573g
• 作为产物：
  描述：

  3,3-二乙氧基羰基-1-硝基-2-苯基丙烷 在 溴 、 三乙胺 作用下， 生成 1-Phenyl-2-nitro-3.3-dicarboaethoxy-cyclopropan
  参考文献：
  名称：

  Sopova,A.S. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 844 - 849

  摘要：

  DOI：

文献信息

• Synthesis of 2,4,5-trisubstituted oxazoles through tin(<scp>iv</scp>) chloride-mediated reaction of trans-2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates with nitriles
  作者：Thangavel Selvi、Kannupal Srinivasan

  DOI：10.1039/c4cc04764h

  日期：——

  trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates when reacted with nitriles in the presence of tin(IV) chloride afford 2,4,5-trisubstituted oxazoles in good to excellent yields. The reactions take place through in situ generation of aroylmethylidene malonates from the cyclopropanes, followed by conjugate addition of nitriles to the malonates to form nitrilium ion intermediates and subsequent cyclisation

  当在氯化锡（IV）存在下与腈反应时，反式-2-芳基-3-硝基-环丙烷-1,1-二羧酸酯以良好或极好的收率得到2,4,5-三取代的恶唑。反应通过从环丙烷原位产生芳酰基亚甲基丙二酸酯来进行，然后将腈共轭加成至丙二酸酯以形成腈离子中间体并随后环化。
• A Convenient Synthesis of Cyclopropanes from Olefin and Carbon Acid Compounds. Synthesis of Tetraethyl Cyclopropanediyldiphosphonates
  作者：Didier Villemin、Frédéric Thibault-Starzyk、Messaoud Hachemi

  DOI：10.1080/00397919408011746

  日期：1994.5

  Abstract Cyclopropane were obtained from electron deficient olefins and acid carbon compounds by oxidation by iodine in the presence of KF on alumina. The reaction allows the synthesis of cyclopropanediyldiphosphonates.

  摘要 环丙烷是由缺电子烯烃和酸性碳化合物在氧化铝上在KF存在下用碘氧化制得的。该反应允许合成环丙烷二基二膦酸酯。
• Reaction of Nitro‐Substituted Donor‐Acceptor Cyclopropanes with Pyrazoles in DMSO: Unexpected Formation of Tandem Kornblum‐Type Ring‐Opening Oxidation/Aza‐Michael Addition Products
  作者：Subaramaniam Thangamalar、Kannupal Srinivasan

  DOI：10.1002/ejoc.202201084

  日期：2023.2.13

  Nitro-substituted donor-acceptor cyclopropanes when heated with pyrazoles in DMSO give oxoamination products through tandem Kornblum-type ring-opening oxidation/aza-Michael addition sequence.

  当在 DMSO 中与吡唑一起加热时，硝基取代的供体-受体环丙烷通过串联 Kornblum 型开环氧化/aza-Michael 加成序列产生氧胺化产物。
• Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers
  作者：Zsolt Rapi、Balázs Démuth、György Keglevich、Alajos Grűn、László Drahos、Péter L. Sóti、Péter Bakó

  DOI：10.1016/j.tetasy.2013.12.007

  日期：2014.1

  The asymmetric Michael addition of diethyl malonate and alpha-substituted diethyl malonates to aromatic nitroalkenes was carried out under mild reaction conditions in a solid-liquid phase transfer reaction in the presence of alpha-D-glucopyranoside- and alpha-D-mannopyranoside-based crown ethers as the catalysts. The use of D-glucose-based lariat ether 1 gave the best results. The substituents of the beta-nitrostyrene and the diethyl malonate had a significant impact on the chemical yields and enantioselectivity. The addition of diethyl-2-acetamidomalonate to aromatic nitroalkenes afforded the corresponding Michael adducts in moderate to high enantiomeric excess (ee up to 99%). The reaction of diethyl-2-methylmalonate with 2-nitro-beta-nitrostyrene gave the adduct with 93% enantiomeric excess in the presence of crown catalyst 1. (C) 2013 Elsevier Ltd. All rights reserved.
• Villemin Didier, Thibault-Starzyk Frederic, Hachemi Messaoud, Synth. Commun, 24 (1994) N 10, S 1425-1431
  作者：Villemin Didier, Thibault-Starzyk Frederic, Hachemi Messaoud

  DOI：——

  日期：——