(S)-2-amino-4-phenyl-4,5-dihydro-4H-benzo[h]chromene-3-carbonitrile | 1262801-77-3

• 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: (S)-2-amino-4-phenyl-4,5-dihydro-4H-benzo[h]chromene-3-carbonitrile
• 英文别名: (S)-2-amino-4-phenyl-5,6-dihydro-4H-benzo[h]chromene-3-carbonitrile；(4S)-2-amino-4-phenyl-5,6-dihydro-4H-benzo[h]chromene-3-carbonitrile
• CAS: 1262801-77-3
• 化学式: C₂₀H₁₆N₂O
• 分子量: 300.36
• InChiKey: XJCLJTWZBOPFRO-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-2-benzylidene-1-tetralone 、 丙二腈 在 C₃₁H₂₉F₃N₄O₃ 作用下， 以 氯仿 为溶剂， 反应 96.0h， 以40%的产率得到(S)-2-amino-4-phenyl-4,5-dihydro-4H-benzo[h]chromene-3-carbonitrile
  参考文献：
  名称：

  邻苯二甲酰胺催化的对苯二酚对苯二酚的迈克尔对映体选择性迈克尔加成† ‡

  摘要：

  对映体的高对映选择性迈克尔加成 丙二腈已经开发了由手性奎宁衍生的方酰胺催化剂催化的查耳酮。在非常低的催化剂负载量（0.5摩尔％）下，这种有机催化反应在温和的反应条件下以高收率和高对映选择性（最高96％ee）产生了手性的γ-氰基羰基化合物。

  DOI：

  10.1039/c1ob06302b

文献信息

• Enantioselective Synthesis of Densely Functionalized Pyranochromenes via an Unpredictable Cascade Michael-Oxa-Michael-Tautomerization Sequence
  作者：Qiao Ren、Yaojun Gao、Jian Wang

  DOI：10.1002/chem.201002490

  日期：2010.12.10

  A surprising example of enantioselective cascade Michael–oxa‐Michael–tautomerization reactions of malononitrile and benzylidenechromanones has been developed. In this case, malononitrile functions as both nucleophile and electrophile. Meanwhile, a simple bifunctional indane amine–thiourea catalyst has been discovered to promote this process to afford high yields (up to 99%) and high to excellent enantiomeric

  已经开发出令人惊讶的丙二腈和亚苄基苯并二氢呋喃酮的对映选择性级联迈克尔-氧杂-迈克尔-互变异构反应的例子。在这种情况下，丙二腈同时具有亲核试剂和亲电子试剂的功能。同时，已经发现一种简单的双功能茚满胺-硫脲催化剂可以促进这一过程，从而提供高收率（高达99％）和高到极好的对映体过量（81-99％ee）。
• Enantioselective synthesis of 2-amino-4H-pyrans via the organocatalytic cascade reaction of malononitrile and α-substituted chalcones
  作者：Zhi-Peng Hu、Wei-Juan Wang、Xiao-Gang Yin、Xue-Jing Zhang、Ming Yan

  DOI：10.1016/j.tetasy.2012.03.018

  日期：2012.4

  An organocatalytic cascade reaction of malononitrile and a-substituted chalcones has been developed for the synthesis of chiral multisubstituted 2-amino-4H-pyran derivatives. A series of chiral primary/tertiary amines and cinchona alkaloids were examined as the catalysts. Quinine was found to be the most efficient catalyst in the absence of any additive. The alpha-substitutents of the chalcones had a siginificant effect on the yield and the enantioselectivity. A number of multisubstituted 2-amino-4H-pyrans were obtained in excellent yields and enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.
• Squaramide-catalyzed enantioselective Michael addition of malononitrile to chalcones
  作者：Wen Yang、Yang Jia、Da-Ming Du

  DOI：10.1039/c1ob06302b

  日期：——

  A highly enantioselective Michael addition of malononitrile to chalcones catalyzed by a chiral quinine-derived squaramide catalyst has been developed. This organocatalytic reaction at a very low catalyst loading (0.5 mol%) led to chiral γ-cyano carbonyl compounds in good yields with high enantioselectivities (up to 96% ee) under mild reaction conditions.

  对映体的高对映选择性迈克尔加成 丙二腈已经开发了由手性奎宁衍生的方酰胺催化剂催化的查耳酮。在非常低的催化剂负载量（0.5摩尔％）下，这种有机催化反应在温和的反应条件下以高收率和高对映选择性（最高96％ee）产生了手性的γ-氰基羰基化合物。