7-chloro-1,3-dihydro-iminoisobenzofuran hydrochloride | 1196988-60-9

• 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: 7-chloro-1,3-dihydro-iminoisobenzofuran hydrochloride
• 英文别名: 7-chloro-3H-2-benzofuran-1-imine;hydrochloride
• CAS: 1196988-60-9
• 化学式: C₈H₆ClNO*ClH
• 分子量: 204.056
• InChiKey: JZRVQTNDRROCDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  12
• 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：

  7-chloro-1,3-dihydro-iminoisobenzofuran hydrochloride 、 (1S,2R)-(-)-1-氨基-2-茚醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以83%的产率得到2-(2'-hydroxymethyl-6'-chlorophenyl)-(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazoline
  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-氯-6甲酰基苯氰 在 sodium tetrahydroborate 、 盐酸 作用下， 以 乙醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到7-chloro-1,3-dihydro-iminoisobenzofuran hydrochloride
  参考文献：
  名称：

  Chiral imidate–ferrocenylphosphanes: synthesis and application as P,N-ligands in iridium(i)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins

  摘要：

  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%）。

  DOI：

  10.1039/c2ob25871d

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。
• 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.
• 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%）。