吖丙啶,2-甲基-1-[(4-甲基苯基)磺酰]-,(2R)- | 177971-32-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 吖丙啶,2-甲基-1-[(4-甲基苯基)磺酰]-,(2R)-
• 英文名称: (2R)-2-methyl-1-(p-tolylsulfonyl)aziridine
• 英文别名: (R)-2-methyl-1-tosylaziridine；(R)-2-methyl-N-tosylaziridine；2-methyl-1-tosylaziridine；Aziridine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-, (2R)-；(2R)-2-methyl-1-(4-methylphenyl)sulfonylaziridine
• CAS: 177971-32-3
• 化学式: C₁₀H₁₃NO₂S
• 分子量: 211.285
• InChiKey: DRZLZRGBQZRSJI-BFHBGLAWSA-N

物化性质

• 沸点：
  326.2±35.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吖丙啶,2-甲基-1-[(4-甲基苯基)磺酰]-,(2R)- 在 manganese(IV) oxide 、 C₇H₆O₂*C₂₀H₂₇NOSi 、 叔丁基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 正戊烷 为溶剂， 反应 13.5h， 生成 2-[(8R,10S)-8-methyl-9-(4-methylphenyl)sulfonyl-1,5-dithia-9-azaspiro[5.5]undecan-10-yl]acetaldehyde
  参考文献：
  名称：

  Stereoselective Synthesis of 2,6-cis- and 2,6-trans-Piperidines through Organocatalytic Aza-Michael Reactions: A Facile Synthesis of (+)-Myrtine and (−)-Epimyrtine

  摘要：

  Both 2,6-cis- and 2,6-trans-piperidines were prepared from common substrates through organocatalytic aza-Michael reactions promoted by the gem-disubstituent effect in conjunction with dithiane coupling reactions. The organocatalytic aza-Michael reaction enabled a facile synthesis of (+)-myrtine and (-)-epimyrtine from a common substrate.

  DOI：

  10.1021/ol103064f
• 作为产物：
  描述：

  N-[(2R)-1-羟基-2-丙基]-4-甲基苯磺酰胺 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 吖丙啶,2-甲基-1-[(4-甲基苯基)磺酰]-,(2R)-
  参考文献：
  名称：

  Absolute configuration of the polyazamacrolides, macrocyclic polyamines produced by a ladybird beetle

  摘要：

  The absolute configuration of the polyazamacrolides, oligomeric macrocycles from the pupal defensive secretion of Epilachna borealis, was determined by comparison of derivatives of the natural material with enantiomerically pure synthetic samples. Samples of a mixture of three (omega-l)-(2-hydroxyethylamino)alkanoic acids and of the corresponding aza-lactones were synthesized from (R)-alaninol. Gas chromatographic comparison of MTPA-amides of the synthetic aza-lactones with the MTPA-amides of aza-lactones prepared from the natural material established that the polyazamacrolides have the (R)-configuration at all stereogenic centers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01404-x

文献信息

• Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions
  作者：Otome E. Okoromoba、Zhou Li、Nicole Robertson、Mark S. Mashuta、Uenifer R. Couto、Cláudio F. Tormena、Bo Xu、Gerald B. Hammond

  DOI：10.1039/c6cc07855a

  日期：——

  We developed an efficient fluorination protocol that converts easily accessible aziridines into [small beta]-fluoroamines, which are important motifs in biologically active molecules. In contrast with traditional fluorination approaches, DMPU-HF has shown...

  我们开发了一种有效的氟化方案，该方案可将易于获得的氮丙啶转化为小β-氟胺，这是生物活性分子中的重要基序。与传统的氟化方法相比，DMPU-HF显示出...
• Sc(OTf)3-catalyzed condensation of 2-alkyl-N-tosylaziridine with aldehydes or ketones: an efficient synthesis of 5-alkyl-1,3-oxazolidines
  作者：Byungman Kang、Aaron W. Miller、Sandra Goyal、SonBinh T. Nguyen

  DOI：10.1039/b902647a

  日期：——

  Sc(OTf)(3) effectively catalyzes the condensation of 2-alkyl-N-tosylaziridine with a wide variety of aldehydes and ketones, producing 5-alkyl-1,3-oxazolidines in good yields and excellent regioselectivity at catalyst loadings as low as 1 mol%.

  Sc（OTf）（3）有效催化2-烷基-N-甲苯磺酰基az啶与各种醛和酮的缩合反应，可在低至催化剂负载量的情况下以高收率和优异的区域选择性制得5-烷基-1,3-恶唑烷。 1摩尔％。
• A Highly Effective Bis(sulfonamide)-Diamine Ligand: A Unique Chiral Skeleton for the Enantioselective Cu-Catalyzed Henry Reaction
  作者：Wei Jin、Xincheng Li、Yongbo Huang、Fan Wu、Boshun Wan

  DOI：10.1002/chem.201000964

  日期：——

  As a unique chiral skeleton, the newly developed bis(sulfonamide)–diamine, which contains both diamine and bis(sulfonamide) moieties, was a highly effective ligand for the asymmetric Cu(OAc)2‐catalyzed Henry reaction between nitromethane and aldehydes with a low catalyst loading at room temperature (see scheme). Both aliphatic and aromatic aldehydes gave excellent enantioselectivities of up to 99 % ee

  壁橱里的骷髅！作为独特的手性骨架，新开发的双（磺酰胺）-二胺同时含有二胺和双（磺酰胺）部分，是不对称Cu（OAc）2催化硝基甲烷与醛之间的亨利反应的高效配体。室温下催化剂负载低（请参阅方案）。脂族和芳族醛均具有高达99％ee的出色对映选择性 。
• Diastereoselective Desymmetrization of <i>p</i>-Quinamines through Regioselective Ring Opening of Epoxides and Aziridines
  作者：Sandip B. Jadhav、Rambabu Chegondi

  DOI：10.1021/acs.orglett.9b04110

  日期：2019.12.20

  A highly diastereoselective desymmetrization of p-quinamines via regioselective ring opening of epoxides and aziridines under mild conditions has been developed. A chairlike six-membered transition state with minimized 1,3-diaxial interactions explains the relative stereoselectivity of the cyclization reaction. This transition-metal free [3 + 3] annulation reaction provides rapid access to fused bicyclic

  已经开发了在温和条件下通过环氧化物和氮丙啶的区域选择性开环对对苯二胺的高度非对映选择性去对称化。具有最小化的1,3-双轴相互作用的椅子状六元过渡态解释了环化反应的相对立体选择性。这种无过渡金属的[3 + 3]环化反应可快速接近具有四取代碳中心的稠合双环吗啉和哌嗪。另外，它还可以通过使用容易获得的手性非外消旋环氧化物和氮丙啶来合成富含对映体的产物。
• A Highly Diastereo- and Enantioselective Copper(I)-Catalyzed Henry Reaction Using a Bis(sulfonamide)−Diamine Ligand
  作者：Wei Jin、Xincheng Li、Boshun Wan

  DOI：10.1021/jo101932a

  日期：2011.1.21

  bis(sulfonamide)−diamine (BSDA) ligands were synthesized from commercially available chiral α-amino alcohols and diamines. The chiral BSDA ligand 3a, coordinated with Cu(I), catalyzes the enantioselective Henry reaction with excellent enantioselectivity (up to 99%). Moreover, with the assistance of pyridine, a CuBr−3a system promotes the diastereoselective Henry reaction with various aldehyde substrates

  从市售的手性α-氨基醇和二胺合成了一系列的双（磺酰胺）-二胺（BSDA）配体。与Cu（I）配位的手性BSDA配体3a以优异的对映选择性（高达99％）催化对映选择性亨利反应。此外，借助吡啶，CuBr- 3a系统可促进与各种醛底物的非对映选择性亨利反应，并以高达99％的收率和32.3：1的顺/反选择性提供相应的顺选择性加合物。顺式加合物的对映体过量为97％。