(R)-3-[(Z)-1-(1-phenyl-ethylamino)-ethylidene]-dihydro-furan-2-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-3-[(Z)-1-(1-phenyl-ethylamino)-ethylidene]-dihydro-furan-2-one
• 英文别名: 3-(1-((R)-1-phenylethylamino)ethylidene)-dihydrofuran-2(3H)-one；(Z)-3-[1-(1-phenylethylamino)ethylidene]tetrahydro-2-furanone；(3Z)-3-[1-[[(1R)-1-phenylethyl]amino]ethylidene]oxolan-2-one
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: FLSOWNVNCMLXAY-QGDAWOFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-[(Z)-1-(1-phenyl-ethylamino)-ethylidene]-dihydro-furan-2-one 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 生成 (S)-2-Oxa-spiro[4.5]dec-7-ene-1,6-dione
  参考文献：
  名称：

  Enantioselective Michael-type reaction of chiral linear α,α-disubstituted secondary enamines

  摘要：

  The enantioselective Michael-type reaction of chiral 2-substituted cyclic imines, reacting as their secondary enamine tautomers, has been extended to a linear ketimine possessing an oxo group on one of the substituents. A single secondary enamine tautomer is observed due to H-bonding of the NH group, thus allowing the reaction to proceed with a high degree of stereoselectivity.

  DOI：

  10.1016/0957-4166(94)80112-6
• 作为产物：
  描述：

  α-乙酰基-γ-丁内酯 、 R(+)-alpha-甲基苄胺 在 indium(III) bromide 作用下， 反应 0.67h， 以95%的产率得到(R)-3-[(Z)-1-(1-phenyl-ethylamino)-ethylidene]-dihydro-furan-2-one
  参考文献：
  名称：

  三溴化铟催化制备β-烯氨基酮和酯的通用有效方法

  摘要：

  在催化量的三溴化铟存在下，通过使β-二羰基化合物与胺反应，可以高产率地合成出多种β-烯胺酮和酯。在无溶剂条件下，反应在室温下以短的反应时间平稳地进行。

  DOI：

  10.1002/adsc.200505268

文献信息

• A General and Efficient Method for the Preparation of β-Enamino Ketones and Esters Catalyzed by Indium Tribromide
  作者：Zhan-Hui Zhang、Liang Yin、Yong-Mei Wang

  DOI：10.1002/adsc.200505268

  日期：2006.1

  A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide. The reaction proceeds smoothly at room temperature in a short reaction time under solvent-free conditions.

  在催化量的三溴化铟存在下，通过使β-二羰基化合物与胺反应，可以高产率地合成出多种β-烯胺酮和酯。在无溶剂条件下，反应在室温下以短的反应时间平稳地进行。
• An Efficient Method for the Enamination of 1,3-Dicarbonyl Compounds with Ceric Ammonium Nitrate (CAN)
  作者：Li-Ping Mo、Shu-Fen Liu、Wan-Zhi Li

  DOI：10.1002/jccs.200700127

  日期：2007.8

  An efficient method for the enamination of 1,3-dicarbonyl compounds by employing ceric ammonium nitrate (CAN) as the catalyst has been described. A variety of β-amino-α,β-unsaturated ketones and esters have been synthesized in excellent yield within a short reaction time under solvent-free conditions.

  已经描述了一种通过使用硝酸铈铵 (CAN) 作为催化剂来烯化 1,3-二羰基化合物的有效方法。在无溶剂条件下，在很短的反应时间内以优异的收率合成了多种 β-氨基-α,β-不饱和酮和酯。
• Stereoselective Reduction of Enantiopure β-Enamino Esters by Hydride:  A Convenient Synthesis of Both Enantiopure β-Amino Esters
  作者：Cristina Cimarelli、Gianni Palmieri

  DOI：10.1021/jo960107y

  日期：1996.1.1

  The reduction of enantiopure beta-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo- and enantioselectivity to yield beta-amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is reported for the origin of the stereoselectivity through an enol ester-diacetoxyborohydride 6, which affords the intramolecular reduction. By choosing the appropriate chiral amine, this procedure allows a straightforward preparation of both the enantiopure beta-amino esters and derivatives with known biological activity, using readily available starting materials and inexpensive reagents and conditions.
• Synthesis of Optically Active (+)-Canangone, Its 6-Epimer, and Determination of Absolute Configuration
  作者：Girish Koripelly、Wolfgang Saak、Jens Christoffers

  DOI：10.1002/ejoc.200700691

  日期：2007.12

  The first synthesis of canangone and its 6-epimer is reported. The products are obtained in optically active form by an asymmetric Robinson annulation. The relative and absolute configuration of the natural product is established for the first time. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  报道了卡南酮及其 6-差向异构体的首次合成。通过不对称罗宾逊环化获得旋光形式的产物。首次建立了天然产物的相对和绝对构型。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Enantioselective Michael-type reaction of chiral linear α,α-disubstituted secondary enamines
  作者：Anasse Felk、Gilbert Revial、Bernard Viossat、Pascale Lemoine、Michael Pfau

  DOI：10.1016/0957-4166(94)80112-6

  日期：1994.8

  The enantioselective Michael-type reaction of chiral 2-substituted cyclic imines, reacting as their secondary enamine tautomers, has been extended to a linear ketimine possessing an oxo group on one of the substituents. A single secondary enamine tautomer is observed due to H-bonding of the NH group, thus allowing the reaction to proceed with a high degree of stereoselectivity.