(S)-N-(2,6-dimethylphenyl)-indoline-2-carboxamide | 926893-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-N-(2,6-dimethylphenyl)-indoline-2-carboxamide
• 英文别名: (2S)-N-(2,6-dimethylphenyl)-2,3-dihydro-1H-indole-2-carboxamide
• CAS: 926893-38-1
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: UEQLTOPBQCFQIG-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-(2,6-dimethylphenyl)-indoline-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (S)-2-(2,6-xylidinomethyl)indoline
  参考文献：
  名称：

  Catalytic asymmetric borane reduction of prochiral ketones by the use of diazaborolidine catalysts prepared from chiral β-diamines

  摘要：

  The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral diazaborolidine catalysts prepared in situ from chiral P-diamines and borane. Chiral secondary alcohols were obtained with modest to high enantiomeric excesses (up to 92% ee) using (S)-2-[(4-trifluoromethyl)anilinomethyl]indoline 2f. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00414-6
• 作为产物：
  描述：

  (S)-吲哚啉-2-羧酸 在 N-甲基吗啉 、 sodium hydroxide 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 34.25h， 生成 (S)-N-(2,6-dimethylphenyl)-indoline-2-carboxamide
  参考文献：
  名称：

  Catalytic asymmetric borane reduction of prochiral ketones by the use of diazaborolidine catalysts prepared from chiral β-diamines

  摘要：

  The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral diazaborolidine catalysts prepared in situ from chiral P-diamines and borane. Chiral secondary alcohols were obtained with modest to high enantiomeric excesses (up to 92% ee) using (S)-2-[(4-trifluoromethyl)anilinomethyl]indoline 2f. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00414-6

文献信息

• Development of New P-Chiral Phosphorodiamidite Ligands Having a Pyrrolo[1,2-<i>c</i>]diazaphosphol-1-one Unit and Their Application to Regio- and Enantioselective Iridium-Catalyzed Allylic Etherification
  作者：Masahiro Kimura、Yasuhiro Uozumi

  DOI：10.1021/jo0615403

  日期：2007.2.1

  designed and prepared. They were preliminarily utilized for iridium-catalyzed asymmetric allylic etherification of cinnamyl carbonate with phenol, where both R- and S-products were obtained with good enantioselectivity (up to 74% ee) by changing the N- and P-substituents of the ligands. The opposite enantioselectivity in iridium-catalyzed allylic substitution was explained by DFT calculations of the energy

  设计并制备了十种具有吡咯并[1,2- c ] [1,3,2]二氮杂磷-1-酮骨架的新型P-手性亚磷酰胺基配体。它们被初步用于铱催化的肉桂酸碳酸酯与苯酚的不对称烯丙基烯丙基醚化反应，通过改变配体的N和P取代基，R和S产物均具有良好的对映选择性（最高74％ee）。通过DFT计算π-烯丙基铱-亚磷酰胺基中间体的能量差，可以解释铱催化的烯丙基取代中相反的对映选择性。