2-(nitromethyl)naphthalene | 4382-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(nitromethyl)naphthalene
• CAS: 4382-19-8
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: CYPDVKKJXBQOOB-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  344.9±11.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  2-(nitromethyl)naphthalene 在 三氟甲磺酸 、 C₂₄H₂₄BNO*C₂HF₃O₂ 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.5h， 生成 [(R)-5-methyl-3-(2-naphthyl)-2-isoxazolin-5-yl]methyl benzoate
  参考文献：
  名称：

  Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group

  摘要：

  1,3-Dipolar cycloadditions of 2-alkylacroleins or atropaldehyde with triisopropylsilyl nitronates bearing an alpha-ary] group produced 3-aryl-2-isoxazolines having a chiral quaternary center in up to 94% ee and up to 88% yield with the aid of Corey's oxazaborolidine catalyst. Specifically, the TIPS nitronate with an alpha-(p-methoxyphenyl) group gave mainly the 2-isoxazolines having an all-carbon quaternary center.

  DOI：

  10.1021/acs.orglett.7b00558
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以21.8 mg的产率得到2-(nitromethyl)naphthalene
  参考文献：
  名称：

  2-Aryl-2-nitroacetates as Central Precursors to Aryl Nitromethanes, α-Ketoesters, and α-Amino Acids

  摘要：

  Nitroarylacetates are useful small molecular building blocks that act as precursors to alpha-ketoesters and aryl nitromethanes as well as alpha-amino acids. Methods were developed that produce each of these compound types in good yields. Two different conditions for decarboxylation are discussed for substrates with neutral and electron-poor aryl groups versus electron-rich aryl groups. For formation of the alpha-ketoesters, new mild conditions for the Nef disproportionation were identified.

  DOI：

  10.1021/jo302071s

文献信息

• Unanticipated Silyl Transfer in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis Using Silyl Nitronates
  作者：Anastassia Matviitsuk、Mark D. Greenhalgh、James E. Taylor、Xuan B. Nguyen、David B. Cordes、Alexandra M. Z. Slawin、David W. Lupton、Andrew D. Smith

  DOI：10.1021/acs.orglett.9b04404

  日期：2020.1.3

  The use of silyl nitronates is reported for the isothiourea-catalyzed synthesis of γ-nitro-substituted silyl esters containing up to two contiguous stereocenters in good yields with excellent enantioselectivities (up to 93% yield and 99:1 er). The serendipitously discovered formation of silyl ester products in this reaction demonstrates a novel platform for catalyst turnover in α,β-unsaturated acyl

  据报道，使用磺酸硅烷基酯用于异硫脲催化的γ-硝基取代的甲硅烷基酯的合成，该γ-硝基取代的甲硅烷基酯的产率高，对映选择性高（产率高达93％，er：99：1 er）。在该反应中偶然发现的甲硅烷基酯产物的形成证明了在α，β-不饱和酰基铵催化中催化剂转换的新平台。
• Metal-Catalyzed Synthesis of Functionalized 1,2,4-Oxadiazoles from Silyl Nitronates and Nitriles
  作者：Paul Nikodemiak、Ulrich Koert

  DOI：10.1002/adsc.201601378

  日期：2017.5.17

  to 1,2,4‐oxadiazoles is described. Silver(I) triflate (AgOTf) and and ytterbium(III) triflate [Yb(OTf)3] are suitable catalysts. A variety of functional groups is tolerated in the nitrile. The reaction works well for alkenyl and aryl silyl nitronates while the use of alkyl silyl nitronates is less efficient. Mechanistic studies are in favour of an elimination of tert‐butyl(dimethyl)silanol (TBSOH) after

  描述了金属催化的甲硅烷基磺酸盐和腈的环加成反应，生成1,2,4-恶二唑。三氟甲磺酸银（I）（AgOTf）和三氟甲磺酸（III）[Yb（OTf）3 ]是合适的催化剂。腈中可耐受多种官能团。该反应对于烯基和芳基甲硅烷基硝酸盐效果很好，而烷基甲硅烷基硝酸盐的使用效率较低。机理研究支持在环加成步骤后消除叔丁基（二甲基）硅烷醇（TBSOH）。该新方法也已经被用于药物紫杉醇的合成。
• Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived <i>N</i>-Boc ketimines catalyzed by chiral phase-transfer catalysts
  作者：Yuxin Liu、Jingdong Wang、Zhonglin Wei、Jungang Cao、Dapeng Liang、Yingjie Lin、Haifeng Duan

  DOI：10.1039/c7nj04527a

  日期：——

  A highly diastereo- and enantioselective nitro-Mannich reaction of isatin-derived ketimines with α-aryl nitromethane catalyzed by Cinchona alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed. A series of 3-substituted 3-amino-oxindoles were constructed using this protocol in excellent yields

  由金鸡纳生物碱衍生的具有多个氢键供体的相转移催化剂催化了靛红衍生的酮亚胺与α-芳基硝基甲烷的高度非对映和对映选择性的硝基曼尼希反应（该反应中使用的第一个无金属催化体系）发达。使用该方案构建了一系列3-取代的3-氨基-羟吲哚，具有优异的收率（96-99％），高对映选择性（高达95％ee）和非对映选择性（高达95：5 dr）。
• L-tert-Leucine derived urea-ammonium salts: Efficient bifunctional phase transfer catalysts for highly diastereo- and enantioselective aza-Henry reaction of isatin-derived N-Boc ketimines with α-aryl nitromethanes
  作者：Jingdong Wang、Yu Liu、Yuxin Liu、Zhonglin Wei、Jungang Cao、Dapeng Liang、Yingjie Lin、Haifeng Duan

  DOI：10.1016/j.tet.2019.04.015

  日期：2019.5

  efficient way of aza-Henry reaction between isatin-derived N-Boc ketimines and α-aryl nitromethanes catalyzed by bifunctional phase transfer catalysts with a quaternary ammonium center derived from L-tert-Leucine has been developed. A series of 3-substituted 3-amino-oxindoles were constructed by this catalytic protocol in excellent yields (90–99%), with high enantioselectivities (83–95%) and diastereoselectivities

  靛红衍生之间氮杂亨利反应的一种有效的方式Ñ -Boc酮亚胺和α与衍生自季铵中心-芳基硝基甲烷催化通过双功能的相转移催化剂大号-叔-亮氨酸已被开发。通过该催化方案，以优异的收率（90–99％），高对映选择性（83–95％）和非对映选择性（79：21–97：3）构建了一系列3-取代的3-氨基-羟吲哚。N -Boc酰胺砜与α的不对称aza-Henry反应还研究了芳基硝基甲烷，并以高对等收率（高达99％）和非对映选择性（高达> 99：1）以高至优异的收率（72-97％）得到了相应的产物。
• Asymmetric Michael addition of α-fluoro-α-nitroalkanes to nitroolefins: facile preparation of fluorinated amines and tetrahydropyrimidines
  作者：Jacek Kwiatkowski、Yixin Lu

  DOI：10.1039/c4cc03513e

  日期：——

  An asymmetric Michael addition of α-fluoro-α-nitroalkanes to nitroolefins was developed, and the products were obtained in good chemical yields and with high stereoselectivities.

  开发了α-氟-α-硝基烷烃对硝基烯烃的不对称Michael加成反应，并且产物在良好的化学产率和高立体选择性下得到。