(R)-2-amino-5,6,7,8-tetrahydro-4-(naphthalen-2-yl)-5-oxo-4H-chromene-3-carbonitrile | 1414846-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-amino-5,6,7,8-tetrahydro-4-(naphthalen-2-yl)-5-oxo-4H-chromene-3-carbonitrile
• 英文别名: (R)-2-amino-5,6,7,8-tetrahydro-4-(2-naphthyl)-5-oxo-4H-chromene-3-carbonitrile；(4R)-2-amino-4-naphthalen-2-yl-5-oxo-4,6,7,8-tetrahydrochromene-3-carbonitrile
• CAS: 1414846-23-3
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: DTBBDSJZFVDPKY-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-naphthylmethylidenemalononitrile 、 1,3-环己二酮 在 C₄₀H₃₁F₆N₃O₂ 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以97%的产率得到(R)-2-amino-5,6,7,8-tetrahydro-4-(naphthalen-2-yl)-5-oxo-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to Benzylidenemalonitriles

  摘要：

  已经开发出由手性二萘基修饰的呋喃酰胺催化剂催化的有机催化对映选择性迈克尔加成反应，从而能够轻松合成具有优异对映选择性（ee高达99%）的相应手性2-氨基-4H-苯并吡喃衍生物。所报道的方法为制备手性2-氨基-4H-苯并吡喃衍生物提供了切实可行的途径。

  DOI：

  10.5012/bkcs.2014.35.1.98

文献信息

• Enantioselective synthesis of 2-amino-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitriles using squaramide as the catalyst
  作者：Yu Gao、Da-Ming Du

  DOI：10.1016/j.tetasy.2012.09.011

  日期：2012.10

  The organocatalyzed enantioselective synthesis of a series of chiral 2-amino-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitriles was achieved using bifunctional squaramides as the catalysts. The tandem Michael addition-cyclization reaction of cyclohexane-1,3-diones and benzylidenemalononitriles gave the corresponding products in excellent yields (up to 99%) and moderate to good enantioselectivities (up to 83% ee). This investigation provides an efficient and useful process for the synthesis of chiral 2-amino-4H-chromenes. (C) 2012 Elsevier Ltd. All rights reserved.
• Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to Benzylidenemalonitriles
  作者：Chang Won Suh、Dae Young Kim

  DOI：10.5012/bkcs.2014.35.1.98

  日期：2014.1.20

  The organocatalytic enantioselective Michael addition reaction promoted by chiral binaphthyl-modified squaramide catalyst have been developed, allowing facile synthesis of the corresponding chiral 2-amino-4H-chromenes derivatives with excellent enantioselectivity (up to 99% ee). The method reported represents a practical entry for the preparation of chiral 2-amino-4H-chromenes derivatives.

  已经开发出由手性二萘基修饰的呋喃酰胺催化剂催化的有机催化对映选择性迈克尔加成反应，从而能够轻松合成具有优异对映选择性（ee高达99%）的相应手性2-氨基-4H-苯并吡喃衍生物。所报道的方法为制备手性2-氨基-4H-苯并吡喃衍生物提供了切实可行的途径。