(S)-2-amino-5,6,7,8-tetrahydro-5-oxo-4-phenyl-4H-chromene-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-amino-5,6,7,8-tetrahydro-5-oxo-4-phenyl-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-5,6,7,8-tetrahydro-5-oxo-4-phenyl-4H-chromene-3-carbonitrile；(4S)-2-amino-5-oxo-4-phenyl-4,6,7,8-tetrahydrochromene-3-carbonitrile
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: HCKBOQXEKJNSSC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  苄烯丙二腈 、 1,3-环己二酮 在 C₄₀H₃₁F₆N₃O₂ 作用下， 以 均三甲苯 为溶剂， 反应 4.0h， 以77%的产率得到
  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

• 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。
• 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.
• Organocatalyzed Enantioselective Synthesis of 2-Amino-4<i>H</i>-chromene Derivatives
  作者：Naresh Ramireddy、Santhi Abbaraju、Derong Ding、Hadi Arman、John C.-G. Zhao

  DOI：10.1002/jhet.2641

  日期：2017.1

  Optically active 2‐amino‐5‐oxo‐5,6,7,8‐tetrahydro‐4H‐chromene‐3‐carboxylates, 2‐amino‐5‐oxo‐5,6,7,8‐tetrahydro‐4H‐chromene‐3‐carbonitriles, and 2‐amino‐8‐oxo‐5,6,7,8‐tetrahydro‐4H‐chromene‐3‐carbonitriles were synthesized. Using cinchona alkaloid‐derived bifunctional catalysts, the corresponding 2‐amino‐4H‐chromene derivatives were obtained in high yields and moderate to high ee values (up to 82% ee)

  光学活性的2-氨基-5-氧代-5,6,7,8-四氢-4- ħ色烯-3-羧酸盐，2-氨基-5-氧代-5,6,7,8-四氢-4- ħ -合成了苯甲基-3-腈和2-氨基-8-氧代5,6,7,8-四氢-4 H-苯甲基-3-腈。使用金鸡纳生物碱衍生的双官能催化剂，相应的2-氨基-4- ħ以高产率获得和中度从1,3-之间串联迈克尔加成环化反应的高ee值的值（高达82％ee）的色烯衍生物环己二酮或1,2-环己二酮和（E）-3-芳基-2-氰基丙烯酸酯或亚烷基丙二腈衍生物。