(1′S,4R)-4-(nitromethyl)spiro[chroman-3,1′-cyclopentane]-2,2′-dione | 1373769-36-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: (1′S,4R)-4-(nitromethyl)spiro[chroman-3,1′-cyclopentane]-2,2′-dione
• 英文别名: (1'S,4R)-4-(nitromethyl)spiro[chroman-3,1'-cyclopentan]-2,2'-dione；(1'S,4R)-4-(nitromethyl)spiro[chroman-3,1'-cyclopentane]-2,2'-dione；(3S,4R)-4-(nitromethyl)spiro[4H-chromene-3,2'-cyclopentane]-1',2-dione
• CAS: 1373769-36-8
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: PXKURKPTUPZARY-YGRLFVJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl (S)-1-[(R)-1-(2-hydroxyphenyl)-2-nitroethyl]-2-oxocyclopentanecarboxyate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以58 mg的产率得到(1′S,4R)-4-(nitromethyl)spiro[chroman-3,1′-cyclopentane]-2,2′-dione
  参考文献：
  名称：

  受支持和不受支持的手性方酰胺作为有机催化剂用于立体选择性迈克尔加成反应：对映体纯的二茂铁和螺并铬烷的合成

  摘要：

  从衍生自天然氨基酸的二胺和可商购的氨基烷基聚苯乙烯树脂开始，已经容易地制备了新型的负载性手性双官能方酸酰胺。在室温下的纯净条件下，这些麦角酰胺在不同的迈克尔添加量下均表现为出色的立体选择性可回收有机催化剂。以2-（2-硝基乙烯基）苯酚为亲电试剂，以优异的收率和对映选择性，反应生成易于转化为4 H-色烯和螺并二氢吡喃酮的中间体。

  DOI：

  10.1021/acs.joc.7b01177

文献信息

• Asymmetric Synthesis of Functionalized Chromans via a One-Pot Organocatalytic Domino Michael-Hemiacetalization or -Lactonization and Dehydration Sequence
  作者：Dieter Enders、Gregor Urbanietz、Robert Hahn、Gerhard Raabe

  DOI：10.1055/s-0031-1289683

  日期：2012.3

  Starting from 2-(nitrovinyl)phenols and various cyclic dicarbonyl nucleophiles, a one-pot thiourea-catalyzed diastereo- and enantioselective synthesis of polyfunctionalized chroman derivatives via a domino Michael-hemiacetalization and dehydration sequence as well as via a domino Michael-lactonization reaction is reported. Cyclopenta[b]chromenes, tricyclic spirochromans, and tetrahydro-1H-xanthenes

  从2-（硝基乙烯基）苯酚和各种环状二羰基亲核试剂开始，通过多米诺米歇尔半缩醛化和脱水序列以及多米诺米歇尔-内酰胺化反应，通过一锅硫脲催化的非对映和对映选择性合成多官能化苯并二氢吡喃衍生物。报告。环戊二烯并[ b ]色烯，三环spirochromans，和四氢ħ -xanthenes轴承的各种官能团的可以以这种方式以良好至优异的产率（56-91％）合成并具有非常好的diastereo-（88-99％ de）和对映选择性（83-99％ee）。 有机催化-多米诺反应-硫脲-一锅法-色原
• Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: synthesis of highly substituted chiral spirodihydrocoumarins
  作者：Dhevalapally B. Ramachary、R. Madhavachary、M. Shiva Prasad

  DOI：10.1039/c2ob07122c

  日期：——

  A general approach to asymmetric synthesis of highly substituted spirodihydrocoumarins with a quaternary stereocenter was achieved through neighboring ortho-hydroxyl group induced sequential Michael–lactonization reactions on 2-(2-nitrovinyl)phenols with alkyl cyclopentanone-2-carboxylates in the presence of a catalytic amount of quinine–NH–thiourea followed by p-TSA.

  在催化作用下，邻邻邻羟基引发的2-（2-硝基乙烯基）苯酚与烷基环戊酮-2-羧酸酯的连续迈克尔-内酯化反应，实现了一种具有四级立体中心的高度取代的螺二氢香豆素的不对称合成的一般方法。的数量奎宁– N H–硫脲其次是p -TSA。
• Asymmetric Synthesis of 3,4-Dihydrocoumarin Motif with an All-Carbon Quaternary Stereocenter <i>via</i> a Michael–Acetalization Sequence with Bifunctional Amine-thiourea Organocatalysts
  作者：Bor-Cherng Hong、Prakash Kotame、Gene-Hsiang Lee

  DOI：10.1021/ol202331j

  日期：2011.11.4

  Asymmetric domino Michael acetalization reactions of 2-hydroxynitrostyrene and 2-oxocyclohexanecarbaldehyde with a bifunctional thioureatertiary-amine organocatalyst, e.g., the Takemoto catalyst, followed by oxidation providing the 1',3-spiro-2'-oxocyclohexan-3,4-dihydrocoumarin having one all-carbon quaternary stereocenter with excellent diastereo- and enantioselectivities (up to >99% ee), are described. The structures and absolute configurations of the products were confirmed by X-ray analysis.