N-phenyl-(S)-indoline-2-carboxamide | 104261-81-6

• 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: N-phenyl-(S)-indoline-2-carboxamide
• 英文别名: anilide of (S)-indoline-2-carboxylic acid；(S)-N-phenylindoline-2-carboxamide；(S)-2-anilinocarbonylindoline；2S-indolinecarboxylic acid anilide；(2S)-2,3-Dihydro-N-phenyl-1H-indole-2-carboxamide；(2S)-N-phenyl-2,3-dihydro-1H-indole-2-carboxamide
• CAS: 104261-81-6
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: AUCXFBMQNSUMHX-AWEZNQCLSA-N

物化性质

• 沸点：
  499.5±34.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  N-phenyl-(S)-indoline-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(S)-2-(anilinomethyl)indoline
  参考文献：
  名称：

  New P-stereogenic triaminophosphines and their derivatives: synthesis, structure, conformational study, and application as chiral ligands

  摘要：

  The synthesis, structural, and conformational studies of new P-chiral triaminophosphines, which feature an indolidine and a 1,2,3,4-tetrahydroquinolidine pattern, respectively, are reported. These compounds can feature very different 3D-structures, although they both could be seen a priori as close derivatives of the previously reported 3-phenyl-1,3-diaza-2-phosphabicyclo[3.3.0]octane. The consequences for the use of such compounds and their derivatives in asymmetric metal-catalysis are discussed on the basis of preliminary results in asymmetric cobalt-catalyzed [6+2] cycloaddition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.013
• 作为产物：
  描述：

  N-叔丁氧羰基-L-吲哚啉-2-甲酸 在 N-甲基吗啉 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.25h， 生成 N-phenyl-(S)-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

• Enantioselective Carbenoid Insertion into Phenolic O–H Bonds with a Chiral Copper(I) Imidazoindolephosphine Complex
  作者：Takao Osako、Duanghathai Panichakul、Yasuhiro Uozumi

  DOI：10.1021/ol202977j

  日期：2012.1.6

  The enantioselective O–H carbenoid insertion reaction with a new chiral copper(I) imidazoindolephosphine complex has been developed. The chiral copper(I) complex catalyzed the insertion of carbenoids derived from α-diazopropionates into the O–H bonds of various phenol derivatives to give the corresponding α-aryloxypropionates with up to 91% ee.

  与新的手性铜（I）咪唑并吲哚膦配合物的对映选择性OH类化合物插入反应已经开发出来。手性铜（I）配合物可催化衍生自α-重氮丙酸酯的类胡萝卜素插入各种酚衍生物的O-H键中，从而得到具有91％ee的相应α-芳氧基丙酸酯。
• Palladium-Catalyzed Asymmetric Suzuki–Miyaura Cross Coupling with Homochiral Phosphine Ligands Having Tetrahydro-1H-imidazo[1,5-a]indole Backbone
  作者：Yasuhiro Uozumi、Yutaka Matsuura、Toshimasa Suzuka、Takayasu Arakawa、Yoichi Yamada

  DOI：10.1055/s-0036-1589407

  日期：——

  nyltetrahydro-1H-imidazo[1,5-a]indol-1-one, bearing PPh2, P(t-Bu)2, and P(c-Hex)2 groups were designed and prepared with a view toward using them in aqueous heterogeneous asymmetric Suzuki–Miyaura biaryl coupling. The asymmetric coupling of 2-substituted 1-iodonaphthalenes and 2-substituted naphthalen-1-ylboronic acid took place in water under heterogeneous conditions in the presence of 10 mol% palladium

  笔者想用这篇文章来教授迪特尔·恩德斯在他70之际个生日。 抽象的 两亲性聚苯乙烯-聚乙二醇树脂负载的手性咪唑并吲哚膦（PS-PEG-L *），（3 R，9a S）-2-芳基-3-（2-二烷基膦基）苯基四氢-1 H-咪唑[1 ，5-一个]吲哚-1-酮，轴承PPH 2，P（吨-Bu）2和P（c ^ -六角）2个基团被设计，并用制备视图朝向在含水多相不对称铃木-宫浦联芳基使用它们耦合。2-取代的1-碘萘和2-取代的萘-1-基硼酸在不均匀条件下于水中在10摩尔％的PS-PEG-L * -Pd络合物钯存在下进行不对称偶联，生成多达94个（的％eeS）-2，2′-二取代的1，1′-联萘基。 两亲性聚苯乙烯-聚乙二醇树脂负载的手性咪唑并吲哚膦（PS-PEG-L *），（3 R，9a S）-2-芳基-3-（2-二烷基膦基）苯基四氢-1 H-咪唑[1 ，5-一个]吲哚-1-酮，轴承PPH 2，P（吨-Bu）2和P（c
• 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。
• New homochiral phosphine ligands having a hexahydro-1H-pyrrolo[1,2-c]imidazolone backbone: preparation and use for palladium-catalyzed asymmetric alkylation of cycloalkenyl carbonates
  作者：Kazutaka Shibatomi、Yasuhiro Uozumi

  DOI：10.1016/s0957-4166(02)00467-6

  日期：2002.8

  New chiral ligands having a pyrrolo[1,2-c]imidazolone backbone were prepared by condensation of anilides of homochiral cyclic amino acids with 2-(diphenylphosphino)benzaldehyde. Of these ligands, (3R,9aS)-(3-(2-diphenylphosphino)phenyl-2-phenyl)tetrahydro-1H-imidazo[1,5-a]indole-1-one was found to be effective for palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl carbonates with dimethyl malonate to give the corresponding dimethyl cycloalkenylmalonates with e.e. of up to 89%. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Catalytic asymmetric borane reduction of prochiral ketones by the use of diazaborolidine catalysts prepared from chiral β-diamines
  作者：Shinsuke Sato、Hiroyasu Watanabe、Masatoshi Asami

  DOI：10.1016/s0957-4166(00)00414-6

  日期：2000.11

  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.