| 1414889-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• CAS: 1414889-32-9
• 化学式: C₂₀H₁₉F₃N₂O₂
• 分子量: 376.378
• InChiKey: OAVAHDLPGKZDQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 Pd[(S)-SynPhos](OCOCF₃)₂ 、 氢气 作用下， 以 2,2,2-三氟乙醇 为溶剂， 50.0 ℃ 、4.83 MPa 条件下， 反应 24.0h， 以96%的产率得到(+)-6-isopropyl-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one
  参考文献：
  名称：

  钯催化氟化喹唑啉酮的不对称氢化

  摘要：

  使用手性Pd /双膦配合物作为催化剂，对一系列氟化喹唑啉酮进行氢化，得到相应的氟化二氢喹唑啉酮，其对映选择性高达98％。

  DOI：

  10.1016/j.tetlet.2013.08.078

文献信息

• Bisphosphine-Triggered One-Pot Sequential [3 + 2]/[3 + 2] Annulation of Allenoates with Cyclic Ketimines
  作者：Li-Jun Yang、Shuai Wang、Jing Nie、Shen Li、Jun-An Ma

  DOI：10.1021/ol402364t

  日期：2013.10.18

  bisphosphine-triggered one-pot sequential [3 + 2]/[3 + 2] annulation of allenoates with cyclic ketimines was developed, in which the product of the first [3 + 2] annulation is the electron-deficient substrate for the second [3 + 2] annulation reaction. The reaction is exceptionally regioselective and diastereoselective. This novel and highly convergent strategy may open up a new viewpoint in utilizing allenoates to prepare

  开发了一种高效的双膦触发的一锅式连续的[3 + 2] / [3 + 2]环烯丙酸酯与环酮亚胺环化反应，其中第一个[3 + 2]环化反应的产物是电子缺陷的底物。第二次[3 + 2]环化反应。该反应是区域选择性和非对映选择性的。这种新颖且高度收敛的策略可以为利用烯丙酸酯制备N-稠合多环化合物开辟新的观点。
• A Highly Regio- and Diastereoselective Phosphane-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Cyclic<i>N</i>-Acyl Ketimines
  作者：Li-Jun Yang、Hua Cai、Jing Nie、Jun-An Ma

  DOI：10.1002/ejoc.201300342

  日期：2013.7

  A highly regio- and diastereoselective phosphane-catalyzed [3+2] annulation of Morita–Baylis–Hillman (MBH) carbonates with cyclic N-acyl-substituted ketimines was developed. In the presence of the catalyst PBu3 (10 mol-%), a series of N-fused tricyclic products were obtained in excellent yields and diastereoselectivities under mild conditions. An example of a catalytic enantioselective annulation is

  开发了一种高度区域选择性和非对映选择性磷烷催化的 Morita-Baylis-Hillman (MBH) 碳酸酯与环状 N-酰基取代的酮亚胺的 [3+2] 环化。在催化剂 PBu3 (10 mol-%) 存在下，在温和条件下以优异的产率和非对映选择性获得了一系列 N-稠合三环产物。还介绍了催化对映选择性环化的一个例子。
• Highly enantioselective organocatalytic Strecker reaction of cyclic N-acyl trifluoromethylketimines: synthesis of anti-HIV drug DPC 083
  作者：Fa-Guang Zhang、Xiao-Yan Zhu、Shen Li、Jing Nie、Jun-An Ma

  DOI：10.1039/c2cc36307k

  日期：——

  A highly efficient, organocatalytic, enantioselective Strecker reaction of cyclic N-acyl ketimines was developed for the preparation of enantioenriched cyclic α-amino nitriles with a quaternary carbon stereocentre and anti-HIV drug DPC 083.

  开发了环状 N-酰基酮亚胺的高效、有机催化、对映选择性 Strecker 反应，用于制备具有季碳立构中心的对映体富集的环状 α-氨基腈和抗 HIV 药物 DPC 083。
• Chiral Phosphoric Acid-Catalyzed Asymmetric Aza-Friedel-Crafts Reaction of Indoles with Cyclic<i>N</i>-Acylketimines: Enantioselective Synthesis of Trifluoromethyldihydroquinazolines
  作者：Ke-Feng Zhang、Jing Nie、Ran Guo、Yan Zheng、Jun-An Ma

  DOI：10.1002/adsc.201300534

  日期：2013.11.25

  AbstractAn enantioselective aza‐Friedel–Crafts (F‐C) reaction of indoles with cyclic N‐acylketimines has been developed. By using chiral phosphoric acid catalysts, a wide range of enantioenriched trifluoromethyldihydroquinazolines was obtained in excellent yields (up to 98%) with good to high enantioselectivities (up to 99% ee).magnified image
• Nucleophilic Lewis Base Dependent Addition Reactions of Allenoates with Trifluoromethylated Cyclic Ketimines
  作者：Li-Jun Yang、Shen Li、Shuai Wang、Jing Nie、Jun-An Ma

  DOI：10.1021/jo500356t

  日期：2014.4.18

  A detailed investigation on the different reactivity patterns shown by phosphorus- and nitrogen-containing Lewis base catalysts in the reactions of allenoates with cyclic trifluoromethyl ketimines was accomplished. With PPh3, [3 + 2] annulations proceeded smoothly to afford dihydropyrrole derivatives in excellent yields. Under the catalysis of DABCO, [2 + 2] annulations occurred, producing azetidine derivatives in good to high yields. However, in the presence of pyridine, alpha,alpha'-disubstituted allenoates were obtained in very high yields via aza-Morita-Baylis-Hillman reactions. These studies provide an opportunity for diverse synthesis of a variety of N-heterocyclic compounds from the same starting materials.