2-甲基-2-硝基-5-氧代己酸乙酯 | 58623-82-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-甲基-2-硝基-5-氧代己酸乙酯
• 英文名称: ethyl 2-methyl-2-nitro-5-oxohexanoate
• CAS: 58623-82-8
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: WTXFHPPAOOOAFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-甲基-2-硝基-5-氧代己酸乙酯 在 5%-palladium/activated carbon 、 氢气 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以98%的产率得到ethyl trans-2,5-dimethyl-2-pyrrolidinecarboxylate
  参考文献：
  名称：

  Synthesis of NP25302

  摘要：

  An efficient synthesis of NP25302 is presented that relies on 5-endo-dig N-cyclization to establish the bicyclic core and Curtius rearrangement to Install the N-acyl vinylogous urea functionality.

  DOI：

  10.1021/ol202381m
• 作为产物：
  描述：

  丁烯酮 、 2-硝基丙酸乙酯 在 Al-Li-(R,R')-2,2'-dihydroxy-1,1'-binaphthyl 作用下， 以 四氢呋喃 为溶剂， 生成 2-甲基-2-硝基-5-氧代己酸乙酯
  参考文献：
  名称：

  α-硝基酯对α，β-不饱和酮的催化对映选择性迈克尔加成反应

  摘要：

  在催化量的手性Al-Li-（R，R'）-2,2'-dihydroxy-1,1的存在下进行α-硝基酯2a-d与α，β-不饱和酮的对映选择性Michael加成反应-1,1'-联萘（“AlLiBINOL”）复合物制备在原位从的LiAlH 4和2.45当量。（R，R'）-BINOL的混合物。迈克尔加成物的对映选择性被证明是极度依赖于温度的：当在室温下进行反应时，迈克尔加成物4a显示7％ee，而相反的4a对映体为72％ee。当在-23℃下进行1，4-加成时发现。溶剂变化表明，四氢呋喃具有最高的选择性（最高80％ee），而对映体的最高对映体选择性在二氯甲烷中（最高25％）。AlLi 3 BINOL 3配合物6的X射线结构分析结合27 Al NMR研究表明，“ AlLiBINOL”是溶液中铝配合物的混合物。

  DOI：

  10.1016/s0957-4166(97)00432-1

文献信息

• Highly Efficient Ytterbium Triflate Catalyzed Michael Additions of α-Nitroesters in Water
  作者：Erik Keller、Ben Feringa

  DOI：10.1055/s-1997-5761

  日期：1997.7

  Michael additions of alpha-nitroesters with enones and alpha,beta-unsaturated aldehydes result in quantitative conversions to the corresponding 1,4-adducts by performing the reactions in water in the presence of ytterbium triflate as water-tolerant Lewis acid.

  通过在三氟甲磺酸镱作为耐水路易斯酸的存在下在水中进行反应，α-硝基酯与烯酮和 α，β-不饱和醛的迈克尔加成导致定量转化为相应的 1,4-加合物。
• Phosphine-boronates: efficient bifunctional organocatalysts for Michael addition
  作者：Olivier Baslé、Susana Porcel、Sonia Ladeira、Ghenwa Bouhadir、Didier Bourissou

  DOI：10.1039/c2cc30399j

  日期：——

  Phosphine-boronates R(2)P(o-C(6)H(4))B(OR')(2) have been evaluated as bifunctional organocatalysts for the Michael addition of malonate pronucleophiles to methylvinylketone. The presence of the Lewis acidic boron center adjacent to phosphorus significantly improves catalytic performance. Isolation and complete characterization of a key intermediate, namely a beta-phosphonium enolate, substantiate the

  膦硼酸酯R（2）P（oC（6）H（4））B（OR'）（2）已被评估为双官能有机催化剂，用于将丙二酸酯前亲核试剂迈克尔加成到甲基乙烯基酮上。与磷相邻的路易斯酸性硼中心的存在显着改善了催化性能。关键中间体，即烯醇β-phosph的分离和完全表征，证实了路易斯酸性部分在催化过程中的作用。
• Asymmetric Michael addition of α-nitro-ketones using catalytic peptides
  作者：Brian R. Linton、Michael H. Reutershan、Christopher M. Aderman、Elizabeth A. Richardson、Kristen R. Brownell、Charles W. Ashley、Catherine A. Evans、Scott J. Miller

  DOI：10.1016/j.tetlet.2007.01.073

  日期：2007.3

  Peptide-based catalysts have been developed that promote the asymmetric Michael addition of nitroalkanes. The most effective peptides contain a beta-turn structural element as well as a basic histidine and an arylsulfonamide-protected arginine. Excellent yields with enantioselectivities of up to 74% ee have been observed. (c) 2007 Elsevier Ltd. All rights reserved.
• Structure Reassignment and Synthesis of Jenamidines A₁/A₂, Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues
  作者：Jeremy R. Duvall、Fanghui Wu、Barry B. Snider

  DOI：10.1021/jo061650+

  日期：2006.10.1

  and C (8-10). Jenamidines A(1)/A(2) (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA ( 76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.