(2R,3S)-3-( p-tolylamino)butan-2-ol | 1342297-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-3-( p-tolylamino)butan-2-ol
• 英文别名: (2R,3S)-3-(4-methylphenylamino)butan-2-ol；(2R,3S)-3-(4-methylanilino)butan-2-ol
• CAS: 1342297-67-9
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: PCIOJWJKROKDJP-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-( p-tolylamino)butan-2-ol 、 (Z)-N-(3-diazo-1-methylindolin-2-ylidene)-4-methylbenzenesulfonamide 在 copper(I) trifluoromethanesulfonate benzene 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以57%的产率得到(Z)-4-methyl-N-((2'R,4'S,5'R)-1,4',5'-trimethyl-3'-(p-tolyl)spiro[indoline-3,2'-oxazolidin]-2-ylidene)benzenesulfonamide
  参考文献：
  名称：

  A copper-catalyzed reaction of 3-diazoindolin-2-imines with 2-(phenylamino)ethanols: convenient access to spiro[indoline-3,2′-oxazolidin]-2-imines

  摘要：

  3-二氮代吲哚啉-2-亚胺在铜催化下与手性2-(苯氨基)乙醇反应，以良好产率和优异的对映选择性生成手性螺[吲哚啉-3,2'-噁唑啉]-2-亚胺。

  DOI：

  10.1039/c7cc09488d
• 作为产物：
  描述：

  乙烷,三氯氟- 、 2,3-trans-epoxybutane 反应 5.0h， 生成 (2R,3S)-3-( p-tolylamino)butan-2-ol
  参考文献：
  名称：

  Alcaide, Benito; Arjona, Odon; Pradilla, Roberto Fernandez de la, Journal of Chemical Research, Miniprint, 1988, # 3, p. 932 - 957

  摘要：

  DOI：

文献信息

• Development of recyclable chiral macrocyclic metal complexes for asymmetric aminolysis of epoxides: application for the synthesis of an enantiopure oxazolidine ring
  作者：Raj Kumar Tak、Manish Kumar、Mohd Nazish、Tushar Kumar Menapara、Rukhsana I. Kureshy、Noor-ul H. Khan

  DOI：10.1039/c8nj02960a

  日期：——

  New recyclable chiral salen complexes Cr(III)1–7 were synthesized from various macrocyclic chiral ligands having multistereogenic chiral centers which work synergistically to give the best results in terms of the enantioselectivity and yield of the products. Among the synthesized complexes, the Cr(III)-4 salen complex efficiently catalyzed the ring opening reaction of various aromatic ester epoxides

  由具有大立体手性中心的各种大环手性配体合成了新的可回收的手性salen配合物Cr（III）1-7，它们在对映选择性和产物收率方面具有协同作用，从而获得最佳结果。在合成的配合物中，Cr（III）-4 salen配合物有效地催化了各种芳族​​酯环氧化物，反式环氧化物和内消旋体的开环反应。-与苯胺形成的环氧化物提供相应的β-氨基-α-羟基酯和β-氨基醇，其ee高达99％，收率高达95％。此外，手性纯的β-氨基-α-羟基酯被转化成药学上重要的恶唑烷环系统。此外，铬催化剂可循环使用多达5个循环，并保持其活性。
• Aminolytic kinetic resolution of trans epoxides for the simultaneous production of chiral trans β-amino alcohols in the presence of chiral Cr(III) salen complex using an ionic liquid as a green reaction media
  作者：Rukhsana I. Kureshy、Manish Kumar、Santosh Agrawal、Noor-ul H. Khan、Sayed H.R. Abdi、Hari C. Bajaj

  DOI：10.1016/j.tetasy.2010.02.021

  日期：2010.3

  Chiral Cr(III) salen complex 1 having t-Bu substituents at 3,3' and 5,5'-positions was used as a catalyst for the highly enantioselective aminolytic kinetic resolution (AKR) of racemic trans epoxides with different anilines as nucleophile in the presence of different ionic liquids at rt. Excellent yields (>98%) of anti beta-aminoalcohols with high enantioselectivity (ee >99%) was achieved in 4 h when [bmim]PF6 was used as the ionic liquid. The present ionic liquid mediated AKR process is recyclable (up to six cycles with no loss in performance) and is five times quicker than the homogeneous process utilizing conventional organic solvents. (C) 2010 Elsevier Ltd. All rights reserved.
• A copper-catalyzed reaction of 3-diazoindolin-2-imines with 2-(phenylamino)ethanols: convenient access to spiro[indoline-3,2′-oxazolidin]-2-imines
  作者：Guorong Sheng、Shicong Ma、Songlin Bai、Jianming Mao、Ping Lu、Yanguang Wang

  DOI：10.1039/c7cc09488d

  日期：——

  3-Diazoindolin-2-imines reacted with chiral 2-(phenylamino)ethanols under copper catalysis to furnish chiral spiro[indoline-3,2′-oxazolidin]-2-imines in good yields with excellent diastereoselectivity.

  3-二氮代吲哚啉-2-亚胺在铜催化下与手性2-(苯氨基)乙醇反应，以良好产率和优异的对映选择性生成手性螺[吲哚啉-3,2'-噁唑啉]-2-亚胺。
• Alcaide, Benito; Arjona, Odon; Pradilla, Roberto Fernandez de la, Journal of Chemical Research, Miniprint, 1988, # 3, p. 932 - 957
  作者：Alcaide, Benito、Arjona, Odon、Pradilla, Roberto Fernandez de la、Plumet, Joaquin、Rodriguez-Campos, Ignacio M.、Santesmases, Maria J.

  DOI：——

  日期：——