(R)-methyl 1-tosylpyrrolidine-2-carboxylate | 1314228-04-0

• 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: (R)-methyl 1-tosylpyrrolidine-2-carboxylate
• 英文别名: methyl (2R)-1-(4-methylphenyl)sulfonylpyrrolidine-2-carboxylate
• CAS: 1314228-04-0
• 化学式: C₁₃H₁₇NO₄S
• 分子量: 283.348
• InChiKey: ZWRPAGBRJCRZON-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methyl 1-tosylpyrrolidine-2-carboxylate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 4.0h， 生成 (R)-α-(S)-phenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol
  参考文献：
  名称：

  Highly Stereoselective Syntheses of Proline-Derived Vicinal Amino Alcohols through Grignard Addition onto N-Tosylprolinal

  摘要：

  A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

  DOI：

  10.1055/s-0035-1560802
• 作为产物：
  描述：

  D-脯氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-methyl 1-tosylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Highly Stereoselective Syntheses of Proline-Derived Vicinal Amino Alcohols through Grignard Addition onto N-Tosylprolinal

  摘要：

  A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

  DOI：

  10.1055/s-0035-1560802

文献信息

• Functionalization of Mesoporous Carbon with Superbasic MgO Nanoparticles for the Efficient Synthesis of Sulfinamides
  作者：Rajashree Chakravarti、Ajayan Mano、Hideo Iwai、Salem S. Aldeyab、R. Pradeep Kumar、M. Lakshmi Kantam、Ajayan Vinu

  DOI：10.1002/chem.201002885

  日期：2011.6.6

  highly crystalline small‐size cubic‐phase MgO nanoparticles with a high dispersion. The basicity of the MgO‐supported mesoporous carbons can also be controlled by simply changing the loading of the MgO and the pore diameter of the support. These materials have been employed as heterogeneous catalysts for the first time in the selective synthesis of sulfinamides. Among the catalysts investigated, the support

  通过简单的湿法浸渍法，已经成功地将具有不同尺寸的高碱性MgO纳米颗粒固定在具有不同孔径的介孔碳上。制备的催化剂已通过多种先进技术进行了表征，例如XRD，氮吸附，电子能量损失谱，高分辨率TEM，X射线光电子能谱以及程序升温脱附的CO 2。XRD结果表明，即使在载体的介孔内部大量装载了MgO纳米颗粒之后，载体的介孔结构仍得以保留。还证明了MgO纳米颗粒在载体上的粒度和分散可以通过简单调节载体的质地参数来精细控制。在研究的载体材料中，具有最大孔径和大孔体积的中孔碳提供了具有高分散性的高度结晶的小尺寸立方相MgO纳米颗粒。MgO负载的中孔碳的碱度也可以通过简单地改变MgO的负载量和载体的孔径来控制。这些材料在亚磺酰胺的选择性合成中首次被用作非均相催化剂。在所研究的催化剂中，具有大孔径和高负载MgO的载体表现出最高的活性，并具有优异的亚磺酰胺收率。该催化剂还显示出比原始MgO纳米颗粒高得多的活性。还
• Counterion-Mediated Hydrogen-Bonding Effects: Mechanistic Study of Gold(I)-Catalyzed Enantioselective Hydroamination of Allenes
  作者：Ji Hye Kim、Sung-Woo Park、Sae Rom Park、Sungyul Lee、Eun Joo Kang

  DOI：10.1002/asia.201100135

  日期：2011.8.1

  A new type of counterion‐mediated syn‐addition mechanism has been presented in gold‐catalyzed enantioselective hydroamination reactions with [(R)‐binap(AuOPNB)2] (OPNB=para‐nitrobenzoate). A combination of both hydrogen bonding and the NAu interaction efficiently controlled the challenging enantioselectivity of allenes.

  两种：一种新型的抗衡离子介导的顺式加成机理已在金催化的与[[ R ] -binap（AuOPNB）2 ]（OPNB =对硝基苯甲酸酯）的对映选择性加氢胺化反应中提出。氢键和NAu相互作用的结合有效地控制了烯的挑战性对映选择性。
• [EN] COPPER CATALYSIS-BASED METHOD FOR PREPARING CARBOXYLIC ACID COMPOUND BY MEANS OF ALCOHOL OXIDATION USING OXYGEN AS OXIDANT<br/>[FR] PROCÉDÉ À BASE DE CATALYSE AU CUIVRE POUR LA PRÉPARATION D'UN COMPOSÉ D'ACIDE CARBOXYLIQUE PAR OXYDATION D'ALCOOL À L'AIDE D'OXYGÈNE EN TANT QU'OXYDANT<br/>[ZH] 一种铜催化的以氧气为氧化剂氧化醇制备羧酸化合物的方法
  申请人：UNIV FUDAN

  公开号：WO2022206399A1

  公开（公告）日：2022-10-06

  本发明公开了一种铜催化的以氧气为氧化剂氧化醇制备羧酸化合物的方法，所述方法具体为在25℃-50℃条件下，在有机溶剂中，以硝酸铜(Cu(NO3)2·3H2O)、2,2,6,6-四甲基哌啶氮氧化物(TEMPO)和酸性的无机盐为催化剂，以氧气或空气作为氧化剂，由醇氧化生成羧酸化合物。本发明操作简单，原料和试剂易得，反应条件温和，产率高，底物官能团兼容性广，反应规模可放大并且整个反应过程对环境友好，不存在污染等诸多优点，是一种适合工业化的方法。
• Copper-Catalyzed Aerobic Oxidation of Primary Alcohols to Carboxylic Acids
  作者：Yibo Yu、Di Zhai、Zhengnan Zhengnan Zhou、Sheng Jiang、Hui Qian、Shengming Ma

  DOI：10.1039/d3cc00963g

  日期：——

  Here, the first copper-catalyzed aerobic oxidation of primary alcohols to carboxylic acids with TEMPO and KHSO4 as the co-catalysts has been developed. The reaction exhibits excellent substrate scope and functional group compatibility under mild conditions. Even the very sensitive chiral alcohols, chiral amino alcohols, and alcohol-containing steroid skeletons may be oxidized to afford the corresponding

  在这里，开发了第一个以 TEMPO 和 KHSO 4作为助催化剂的铜催化伯醇有氧氧化成羧酸的反应。该反应在温和条件下表现出优异的底物范围和官能团相容性。即使是非常敏感的手性醇、手性氨基醇和含醇的类固醇骨架也可以被氧化以提供相应的羧酸或内酯而无需外消旋化。
• Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by <i>N</i>-Iodosulfonamides
  作者：Nieves R. Paz、Dionisio Rodríguez-Sosa、Haydee Valdés、Ricardo Marticorena、Daniel Melián、M. Belén Copano、Concepción C. González、Antonio J. Herrera

  DOI：10.1021/acs.orglett.5b00866

  日期：2015.5.15

  Mechanistic evidence observed in Hofmann-Loffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity.