(E)-3-(2-nitrovinyl)-1-tosyl-1H-indole | 373392-59-7

• 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: (E)-3-(2-nitrovinyl)-1-tosyl-1H-indole
• 英文别名: 1-[(4-Methylbenzene)sulfonyl]-3-[2-nitroethenyl]indole；1-(4-methylphenyl)sulfonyl-3-[(E)-2-nitroethenyl]indole
• CAS: 373392-59-7
• 化学式: C₁₇H₁₄N₂O₄S
• 分子量: 342.375
• InChiKey: AKMLKWKFZXBRNB-ZHACJKMWSA-N

物化性质

• 沸点：
  568.7±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-nitrovinyl)-1-tosyl-1H-indole 在 sodium tetrahydroborate 、 silica gel 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 2.0h， 以68%的产率得到3-(2-nitroethyl)-1-tosyl-1H-indole
  参考文献：
  名称：

  Oxetanyl Peptides: Novel Peptidomimetic Modules for Medicinal Chemistry

  摘要：

  The synthesis of novel oxetanyl peptides, where the amide bond is replaced by a non-hydrolyzable oxetanylamine fragment, is reported. This new class of pseudo-dipeptides with the same H-bond donor/acceptor pattern found in proteins expands the repertoire of peptidomimetics.

  DOI：

  10.1021/ol501590n
• 作为产物：
  描述：

  吲哚 在 ammonium acetate 、 三氯氧磷 作用下， 生成 (E)-3-(2-nitrovinyl)-1-tosyl-1H-indole
  参考文献：
  名称：

  Organocatalytic Asymmetric Michael Addition of Aliphatic Aldehydes to Indolylnitroalkenes: Access to Contiguous Stereogenic Tryptamine Precursors

  摘要：

  Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1-ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.

  DOI：

  10.1021/jo3024945

文献信息

• Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea
  作者：Tomotaka Okino、Yasutaka Hoashi、Tomihiro Furukawa、Xuenong Xu、Yoshiji Takemoto

  DOI：10.1021/ja044370p

  日期：2005.1.1

  thiourea moiety and an amino group on a chiral scaffold. Among them, thiourea 1e bearing 3,5-bis(trifluoromethyl)benzene and dimethylamino groups was revealed to be highly efficient for the asymmetric Michael reaction of 1,3-dicarbonyl compounds to nitroolefins. Furthermore, we have developed a new synthetic route for (R)-(-)-baclofen and a chiral quaternary carbon center with high enantioselectivity by Michael

  我们在手性支架上合成了一类带有硫脲部分和氨基的新型双功能催化剂。其中，带有 3,5-双（三氟甲基）苯和二甲氨基的硫脲 1e 被证明对于 1,3-二羰基化合物到硝基烯烃的不对称迈克尔反应非常有效。此外，我们通过迈克尔反应开发了 (R)-(-)-巴氯芬和具有高对映选择性的手性季碳中心的新合成路线。在这些反应中，我们假设催化剂的硫脲部分和氨基分别活化硝基烯烃和 1,3-二羰基化合物，以提供具有高对映选择性和非对映选择性的迈克尔加合物。
• Total Synthesis of (±)-Hapalindole Q
  作者：Aaron C. Kinsman、Michael A. Kerr

  DOI：10.1021/ol0165138

  日期：2001.10.1

  [reaction: see text] The total synthesis of the antibacterial and antimycotic alkaloid hapalindole Q has been achieved in eight steps and 12.4% overall yield. The key step involves a regio- and diastereoselective Diels-Alder reaction to afford a bicyclo[2.2.2]oct-2-ene. This cycloadduct was subsequently dihydroxylated, cleaved, and converted to the natural product.

  [反应：见正文]抗菌和抗真菌生物碱哈达吲哚Q的总合成历经8个步骤，总产率为12.4％。关键步骤涉及区域和非对映选择性的Diels-Alder反应，得​​到双环[2.2.2]辛-2-烯。随后将该环加合物二羟基化，裂解并转化为天然产物。
• Diversity-Oriented One-Pot Synthesis to Construct Functionalized Chroman-2-one Derivatives and Other Heterocyclic Compounds
  作者：Ying-Han Chen、Xue-Li Sun、Hua-Shi Guan、Yan-Kai Liu

  DOI：10.1021/acs.joc.7b00461

  日期：2017.5.5

  The asymmetric organocatalyzed diversity-oriented one-pot synthesis has been developed to construct chroman-2-one derivatives and other heterocyclic compounds with excellent efficiency and stereoselectivity. The reactions represent a challenging issue, since it altered the inherent selectivity profiles exhibited by the substrates of 2-hydroxycinnamaldehyde 1 and trans-β-nitrostyrene 2, which was previously

  已经开发了不对称的有机催化的面向多样性的一锅合成法，以优异的效率和立体选择性构建了苯并二氢-2-酮衍生物和其他杂环化合物。反应代表了一个具有挑战性的问题，因为它改变了2-羟基肉桂醛1和反式-β-硝基苯乙烯2的底物所表现出的固有选择性。，以前被报道为不对称的oxa-Michael-Michael级联生成手性色度。应当指出，在许多天然产物和生物学上感兴趣的分子中发现的含多环O，O-乙缩醛的化合物，也可以作为具有五个连续的立体异构中心的单一非对映异构体，以良好的对映选择性和良好的收率获得。
• Organocatalytic enantioselective synthesis of β-amino sulfonic acid derivatives
  作者：Emmanuel Deau、Alexandra Le Foll、Clémence Fouache、Emilie Corrot、Laetitia Bailly、Vincent Levacher、Pierric Marchand、Florian Querniard、Laurent Bischoff、Jean-François Brière

  DOI：10.1039/d1cc03477d

  日期：——

  An unprecedented enantioselective conjugate addition reaction of sodium bisulfite to various nitrostyrenes occurred upon the influence of a bifunctional amino-thiourea organocatalyst; a strategy that opens a straightforward route to unprotected chiral taurine derivatives thanks to the reduction of the obtained β-nitroethanesulfonic acids into the corresponding amino derivatives.

  在双功能氨基硫脲有机催化剂的影响下，发生了前所未有的亚硫酸氢钠与各种硝基苯乙烯的对映选择性共轭加成反应；由于将获得的 β-硝基乙磺酸还原为相应的氨基衍生物，该策略为未保护的手性牛磺酸衍生物开辟了一条直接途径。
• Highly Selective Diels−Alder Reactions of Dienophiles with 1,3-Cyclohexadiene Mediated by Yb(OTf)₃·2H₂O and Ultrahigh Pressures
  作者：Aaron C. Kinsman、Michael A. Kerr

  DOI：10.1021/ol0065773

  日期：2000.11.1

  [GRAPHICS]Ultrahigh pressures and catalytic Yb(OTf)(3). 2H(2)O were found to mediate Diets-Alder reactions of various electron-deficient dienophiles with 1,3-cyclohexadiene to produce endo-bicyclo[2.2.2]oct-2-enes in moderate to excellent yield and selectivity. The proposed total synthesis of hapalindole Q based on bicyclo[2.2.2]oct-2-ene construction by Diels-Alder reaction and subsequent olefin cleavage is outlined, Preliminary results demonstrating the viability of this strategy are presented.