2-nitro-3H-benzo[f]chromene | 94740-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-nitro-3H-benzo[f]chromene
• CAS: 94740-83-7
• 化学式: C₁₃H₉NO₃
• 分子量: 227.219
• InChiKey: UONSORKZNMKNFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C(Solv: hexane (110-54-3))
• 沸点：
  416.6±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-nitro-3H-benzo[f]chromene 在 sodium tetrahydroborate 、 silica gel 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 0.25h， 以95%的产率得到3,4-dihydro-3-nitro-2H-1-naphtho<1,2-b>pyran
  参考文献：
  名称：

  3,4-Dihydro-3-amino-2H-1-benzopyran Derivatives as 5-HT1A Receptor Ligands and Potential Anxiolytic Agents. 1. Synthesis and Structure-Activity Relationship Studies

  摘要：

  A series of 3,4-dihydro-3-amino-2H-1-benzopyran derivatives were prepared in order to determine the necessary structural requirements for good affinity for 5-HT1A receptors and high selectivity versus other receptors. Modifications of the extracyclic amino substituents, the length of the alkyl side chains, and their substituents were explored. The best compounds (9g, 9k, 15b, 15d) possess imido or sulfonamido functional groups with, a preferential length of four methylenes for the side chain. After resolution, the dextrorotatory enantiomers showed better affinity and selectivity for 5-HT1A receptors. These compounds have been proven to be full agonists. 9g and its enantiomers showed anxiolytic activity in vivo in various comportemental models. The compound (+)-9g is currently under clinical investigation.

  DOI：

  10.1021/jm00038a007
• 作为产物：
  描述：

  2-硝基乙醇 、 2-羟基-1-萘甲醛 在 苯酐 、 二正丁胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以25%的产率得到2-nitro-3H-benzo[f]chromene
  参考文献：
  名称：

  通过有机催化三重多米诺反应的功能化三环色氨酸的不对称合成。

  摘要：

  已经开发出用于合成官能化的三环苯并二氢吡喃骨架的高度立体选择性的三重多米诺反应。脂族醛，硝基色烯和α，β-不饱和醛之间的仲胺催化的多米诺Michael / Michael / aldol缩合反应导致形成重要的具有三个连续立体中心的合成重要的三环苯并二氢吡喃中心，包括收率高的四取代碳（ 20–66％）和出色的立体选择性（> 20：1 dr和> 99％ee）。

  DOI：

  10.1021/acs.orglett.7b01322

文献信息

• Intensified synthesis of [3,4-d]triazole-fused chromenes, coumarins, and quinolones
  作者：Georg Schwendt、Toma Glasnov

  DOI：10.1007/s00706-016-1885-5

  日期：2017.1

  AbstractEfficient and metal-free synthesis of [3,4-d]triazole-fused chromenes, coumarins, and quinolones has been achieved in an intensified regime using microwave heating. The smooth 1,3-dipolar cycloaddition reaction of heterocyclic nitroalkenes with sodium azide provides a rapid entry into valuable heterocyclic scaffolds with potential biological properties. Graphical abstract

  摘要使用微波加热在强化过程中​​已经实现了[3,4- d ]三唑稠合的色烯，香豆素和喹诺酮的高效无金属合成。杂环硝基烯烃与叠氮化钠的平滑1,3-偶极环加成反应可快速进入有价值的具有潜在生物学特性的杂环支架。 图形概要
• Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives
  作者：Jun-Hua Li、Da-Ming Du

  DOI：10.1039/c5ob01211b

  日期：——

  tetrahydro-6H-benzo[c]chromenes and their derivatives has been developed. The corresponding products were obtained by the cascade double Michael addition of 3-nitro-2H-chromenes and their derivatives with α,β-unsaturated ketones catalyzed by a combination of a quinine-derived primary amine and benzoic acid. Through this methodology, the desired products could be obtained in moderate to good yields (up to

  已经开发出用于不对称构造对映体富集的四氢-6 H-苯并[ c ]色烯及其衍生物的有效方案。相应的产物通过将3-硝基-2 H-色酮及其衍生物与奎宁衍生的伯胺和苯甲酸的组合催化的α，β-不饱和酮进行级联双迈克尔加成而获得。通过这种方法，可以以中等至良好的收率（高达90％），具有优异的非对映选择性（高达> 25：1 dr）和中等至优异的对映选择性（高达95％ee）获得所需的产物。
• Enantioselective synthesis of chiral heterocycles containing both chroman and pyrazolone derivatives catalysed by a chiral squaramide
  作者：Jun-Hua Li、Da-Ming Du

  DOI：10.1039/c4ob02653e

  日期：——

  An efficient chiral squaramide-catalysed enantioselective Michael addition of pyrazolin-5-ones to 3-nitro-2H-chromenes afforded chiral heterocycles containing both chroman and pyrazolone derivatives in high to excellent yields (up to 98%) with high enantioselectivities (up to 96%) under very low catalyst loading (0.2 mol%).

  一个高效的手性方酰胺催化的选择性马克尔加成反应，将吡唑啉-5-酮加到3-硝基-2H-色醇中，得到含有色醇和吡唑酮衍生物的手性杂环化合物，收率高达98%，对映选择性高达96%，在非常低的催化剂负载下（0.2 mol%）。
• Asymmetric Friedel–Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes
  作者：Yang Jia、Wen Yang、Da-Ming Du

  DOI：10.1039/c2ob25360g

  日期：——

  enantioselective Friedel–Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes has been developed. This asymmetric Friedel–Crafts alkylation led to medicinally privileged indolyl(nitro)chromans in good yields with high enantioselectivities (up to 95% ee) and diastereoselectivities under mild reaction conditions.

  已经开发了由二苯胺连接的双（恶唑啉）和双（噻唑啉）Zn（II）配合物催化的3-硝基-2 H-色烯对吲哚的高效非对映和对映选择性弗瑞德-克拉夫茨烷基化反应。这种不对称的Friedel-Crafts烷基化反应可得到医学上享有优势的吲哚基（硝基）苯并二氢吡喃，并具有高对映选择性（最高95％ee）和在温和反应条件下的非对映选择性。
• Enantioselective [4+2] Cycloadditions of 2-Vinyl-1 H-indoles with 3-Nitro-2 H-chromenes Catalyzed by a Zn(OTf)2/Bis(oxazoline) Complex: An Efficient Approach to Fused Heterocycles with a Quaternary Stereocenter
  作者：Fen Tan、Cong Xiao、Hong-Gang Cheng、Wei Wu、Ke-Rong Ding、Wen-Jing Xiao

  DOI：10.1002/asia.201100820

  日期：2012.3.5

  There's a ringer: The asymmetric [4+2] cycloaddition reaction of 3‐nitro‐2H‐chromenes with 1‐benzyl‐2‐vinyl‐1H‐indoles catalyzed by Zn(OTf)2 with bis(oxazoline) ligands offers a practical and efficient method to synthesize a variety of fused heterocycles bearing a quaternary stereocenter with good reaction efficiency (up to 94% yield) and excellent stereoselectivities (up to 96% ee, >95:5 d.r.).

  有一个铃声：由Zn（OTf）2和双（恶唑啉）配体催化的3-硝基-2 H-色烯与1-苄基-2-乙烯基-1 H-吲哚的不对称[4 + 2]环加成反应提供了一个一种实用且有效的方法来合成具有四级立体中心的各种稠合杂环，具有良好的反应效率（最高94％的收率）和出色的立体选择性（最高96％ee，> 95：5 dr）。