(S)-benzyl 2-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-ylcarbamoyl]pyrrolidine-1-carboxylate | 810669-97-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-benzyl 2-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-ylcarbamoyl]pyrrolidine-1-carboxylate
• 英文别名: benzyl (2S)-2-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 810669-97-7
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: ABJABNYLXPRXBS-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-ylcarbamoyl]pyrrolidine-1-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以85%的产率得到(2S)-N-[(1S,2R)-2,3-dihydro-2-hydroxy-1H-inden-1-yl]pyrrolidine-2-carboxamide
  参考文献：
  名称：

  通过 1,2-氨基醇衍生的脯氨酰胺作为双功能催化剂，酮与 β-硝基苯乙烯的不对称共轭加成

  摘要：

  这项工作得到了教育部长和 Ciencia 的 Direccion General de Investigacion (CTQ2004-00808/BQU)、Generalitat Valenciana (CTIOIB/2002/320、GRUPOS03/134、GRUPOS05/11 和 GV05) 和 GV05/阿利坎特大学。

  DOI：

  10.1002/ejoc.200700031
• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 在 TEA 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-benzyl 2-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-ylcarbamoyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Enantioselective conjugate addition of ketones to β-nitrostyrenes catalyzed by 1,2-amino alcohol-derived prolinamides

  摘要：

  Various L-prolinamides 14, prepared from L-proline and chiral beta-amino alcohols, are active bifunctional catalysts for the direct nitro-Michael addition of ketones to beta-nitrostyrenes. In particular, catalyst 14e prepared from L-proline and (1S,2R)-cis-1amino-2-indanol exhibits the highest catalytic performance working in polar aprotic solvents such as NMP. High syn-diastereoselectivities (up to 94% de) and good enantioselectivities (up to 80% ee) were obtained at rt. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.023

文献信息

• Asymmetric Conjugate Addition of Ketones to β-Nitrostyrenes by Means of 1,2-Amino-Alcohol-Derived Prolinamides as Bifunctional Catalysts
  作者：Diana Almaşi、Diego A. Alonso、Enrique Gómez-Bengoa、Yvonne Nagel、Carmen Nájera

  DOI：10.1002/ejoc.200700031

  日期：2007.5

  This work has been supported by the Direccion General de Investigacion of the Ministerio de Educacion y Ciencia (CTQ2004-00808/BQU), by the Generalitat Valenciana (CTIOIB/2002/320, GRUPOS03/134, GRUPOS05/11 and GV05/157) and the University of Alicante.

  这项工作得到了教育部长和 Ciencia 的 Direccion General de Investigacion (CTQ2004-00808/BQU)、Generalitat Valenciana (CTIOIB/2002/320、GRUPOS03/134、GRUPOS05/11 和 GV05) 和 GV05/阿利坎特大学。
• Evaluation of Ligands for Ketone Reduction by Asymmetric Hydride Transfer in Water by Multi‐Substrate Screening
  作者：Saoussen Zeror、Jacqueline Collin、Jean‐Claude Fiaud、Louisa Aribi Zouioueche

  DOI：10.1002/adsc.200700272

  日期：2008.1.4

  Various ligands for the ruthenium-catalyzed enantioselective reduction of ketones in water have been investigated. Multi-substrate reactions have been carried out for the comparison of various proline amides and aminoalcohol ligands. Two sets of six aromatic ketones have been selected in order to evaluate the enantiomeric excesses of all the resulting alcohols by a single chromatographic analysis.

  已经研究了用于钌催化的水中酮对映选择性还原的各种配体。为了比较各种脯氨酸酰胺和氨基醇配体，已经进行了多底物反应。为了通过单次色谱分析评估所有所得醇的对映体过量，已选择了两组六种芳族酮。由（1 R，2 S）-顺式制备的脯氨酸酰胺衍生物-氨基茚满醇显示为多底物还原反应中使用的大多数酮的最佳配体。该配体已用于多种其他芳香族酮的对映选择性还原，并且在所有情况下，与我们以前的工作中使用的苯脯氨酰胺相比，对映体过量都得到了改善。
• Synthesis of a New Proline‐Derived Organic Catalyst and Its Evaluation for Direct Aldol Reaction
  作者：Shinji Tanimori、Toshihito Naka、Mitsunori Kirihata

  DOI：10.1081/scc-200036576

  日期：2004.12.31

  Abstract Aldol condensation of isobutylaldehyde with acetone catalyzed by amides and amines (1–8) derived from L‐proline gave β‐hydroxy ketone 17 in 80%ee.

  摘要 在衍生自 L-脯氨酸的酰胺和胺 (1-8) 的催化下，异丁醛与丙酮的羟醛缩合得到 80%ee 的 β-羟基酮 17。
• Prolinamides<i>versus</i>Prolinethioamides as Recyclable Catalysts in the Enantioselective Solvent-Free Inter- and Intramolecular Aldol Reactions
  作者：Diana Almaşi、Diego A. Alonso、Carmen Nájera

  DOI：10.1002/adsc.200800430

  日期：2008.11.3

  and direct anti-aldol reaction of aliphatic ketones with aromatic aldehydes catalyzed by recyclable L-prolineamides and L-prolinethioamides 3 is studied. The L-prolinethioamide 3d (5 mol%), derived from L-Pro and (R)-1-aminoindane, is the most efficient catalyst for this process affording the anti-aldol adducts in high yields with excellent diastereo- and enantioselectivities (up to >98/2 dr, up to

  研究了可回收的L-脯氨酸酰胺和L-脯氨酸硫酰胺3催化的脂肪族酮与芳族醛的无溶剂不对称和直接的抗醛醇缩合反应。衍生自L-Pro和（R）-1-氨基茚满的L-脯氨酸硫代酰胺3d（5 mol％）是该方法最有效的催化剂，可提供高收率的抗醛醇加合物，并具有出色的非对映体和对映体选择性（up在0°C或室温下达到> 98/2 dr，最高可达98％ee）。脯氨酸硫酰胺3d是有效的有机催化剂，可用于首个不对称，无溶剂的分子内Hajos-Parrish-Eder-Sauer-Wiechert反应，其对映选择性（据报道高达88％ee）与有机溶剂中的对映选择性相当或更高。而且，有机催化剂3d可以通过简单的酸/碱萃取容易地回收和再利用。
• Enantioselective conjugate addition of ketones to β-nitrostyrenes catalyzed by 1,2-amino alcohol-derived prolinamides
  作者：Diana Almaşi、Diego A. Alonso、Carmen Nájera

  DOI：10.1016/j.tetasy.2006.07.023

  日期：2006.8

  Various L-prolinamides 14, prepared from L-proline and chiral beta-amino alcohols, are active bifunctional catalysts for the direct nitro-Michael addition of ketones to beta-nitrostyrenes. In particular, catalyst 14e prepared from L-proline and (1S,2R)-cis-1amino-2-indanol exhibits the highest catalytic performance working in polar aprotic solvents such as NMP. High syn-diastereoselectivities (up to 94% de) and good enantioselectivities (up to 80% ee) were obtained at rt. (c) 2006 Elsevier Ltd. All rights reserved.