1,3-dihydro-1-iminoisobenzofuran hydrochloride | 1195988-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1,3-dihydro-1-iminoisobenzofuran hydrochloride
• 英文别名: 1,3-dihydro-iminoisobenzofuran hydrochloride；1,3-dihydro-iminoisobenzofuranhydrochloride；Isobenzofuran-1(3H)-imine hydrochloride；3H-2-benzofuran-1-imine;hydrochloride
• CAS: 1195988-94-3
• 化学式: C₈H₇NO*ClH
• 分子量: 169.611
• InChiKey: KFPMWAYLKGSXAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  33.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-缬氨醇 、 1,3-dihydro-1-iminoisobenzofuran hydrochloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以100%的产率得到(S)-2-(2'-hydroxymethylphenyl)-4-i-propyloxazoline
  参考文献：
  名称：

  Efficient one-step synthesis of chiral bidentate oxazoline-alcohol ligands via a cyclic imidate ester rearrangement

  摘要：

  Various chiral bidentate oxazoline-alcohol ligands were obtained in a straightforward one-step synthesis via a cyclic imidate ester rearrangement. These chiral ligands were tested and compared in asymmetric diethylzinc additions to aldehydes resulting in selectivities of up to 87% ee. An interesting chirality switch was observed when a CPh2-tether instead of a CH2 was present, offering the opportunity for dual stereocontrol. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.038
• 作为产物：
  描述：

  2-氰基苯甲醛 在 sodium tetrahydroborate 、 乙醇 、 盐酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到1,3-dihydro-1-iminoisobenzofuran hydrochloride
  参考文献：
  名称：

  手性酰亚胺作为一种新型的基于氮的手性配体：不对称叠氮化和二乙基锌添加物中的合成和催化活性

  摘要：

  一步有效地合成高产率的手性酰亚胺化物（七个实施例）。这些手性酰亚胺被用作肉桂酸甲酯的Cu（I）催化的不对称叠氮基化和苯甲醛的不对称二乙基锌加成中的配体作为原理证明。亚氨酸酯催化剂体系显示出高催化活性并引起令人鼓舞的选择性。包括对亚氨酸酯-Cu（I）配合物的X射线结构分析，显示了扭曲的四面体排列，金属周围有两个双齿配体分子。

  DOI：

  10.1016/j.tet.2009.08.028

文献信息

• CYCLIC IMIDATE LIGANDS
  申请人：Noël Timothy

  公开号：US20120077989A1

  公开（公告）日：2012-03-29

  The present invention relates to a use of a cyclic imidate as a ligand for catalysis in which the ligand contains sub-structure (Y) as a minimal structural motive, wherein the carbon atoms and the nitrogen atom can be optionally substituted by a chemical substituent.

  本发明涉及将环戊二酰亚胺用作催化剂中的配体的用途，其中该配体包含亚结构（Y）作为最小结构动机，其中碳原子和氮原子可以选择性地被化学取代基取代。
• Chiral imidates as a new class of nitrogen-based chiral ligands: synthesis and catalytic activity in asymmetric aziridinations and diethylzinc additions
  作者：Timothy Noël、Koen Vandyck、Koen Robeyns、Luc Van Meervelt、Johan Van der Eycken

  DOI：10.1016/j.tet.2009.08.028

  日期：2009.10

  Chiral imidates were efficiently synthesized in one step and with high yields (seven examples). These chiral imidates were used as ligands in the Cu(I)-catalyzed asymmetric aziridination of methyl cinnamate and in the asymmetric diethylzinc additions to benzaldehyde as a proof of principle. The imidate catalyst system showed high catalytic activities and induced encouraging selectivities. An X-ray

  一步有效地合成高产率的手性酰亚胺化物（七个实施例）。这些手性酰亚胺被用作肉桂酸甲酯的Cu（I）催化的不对称叠氮基化和苯甲醛的不对称二乙基锌加成中的配体作为原理证明。亚氨酸酯催化剂体系显示出高催化活性并引起令人鼓舞的选择性。包括对亚氨酸酯-Cu（I）配合物的X射线结构分析，显示了扭曲的四面体排列，金属周围有两个双齿配体分子。
• Chiral imidate–ferrocenylphosphanes: synthesis and application as P,N-ligands in iridium(i)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins
  作者：Katrien Bert、Timothy Noël、Wim Kimpe、Jan L. Goeman、Johan Van der Eycken

  DOI：10.1039/c2ob25871d

  日期：——

  A small library of chiral imidate–ferrocenylphosphane ligands was efficiently synthesized (8 examples) and evaluated in the iridium(I)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins. These catalysts perform very well in a range of examples (yields and ee's up to 100%).

  高效合成了一小类手性咪唑酰亚胺–铁烯基膦配体（8个例子），并在铱(I)催化的未功能化和功能化较差的烯烃的加氢反应中进行了评估。这些催化剂在一系列的例子中表现非常良好（产率和对映体过量高达100%）。
• Efficient one-step synthesis of chiral bidentate oxazoline-alcohol ligands via a cyclic imidate ester rearrangement
  作者：Timothy Noël、Koen Robeyns、Luc Van Meervelt、Erik Van der Eycken、Johan Van der Eycken

  DOI：10.1016/j.tetasy.2009.07.038

  日期：2009.9

  Various chiral bidentate oxazoline-alcohol ligands were obtained in a straightforward one-step synthesis via a cyclic imidate ester rearrangement. These chiral ligands were tested and compared in asymmetric diethylzinc additions to aldehydes resulting in selectivities of up to 87% ee. An interesting chirality switch was observed when a CPh2-tether instead of a CH2 was present, offering the opportunity for dual stereocontrol. (C) 2009 Elsevier Ltd. All rights reserved.