2-methyl-3-phenyl-1-tosylaziridine-2-carbaldehyde | 1316098-54-0

• 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: 2-methyl-3-phenyl-1-tosylaziridine-2-carbaldehyde
• 英文别名: (2S,3R)-2-methyl-3-phenyl-1-tosylaziridine-2-carbaldehyde
• CAS: 1316098-54-0
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: LWXZIYXAIMITEB-OWZOALSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54.22
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methyl-3-phenyl-1-tosylaziridine-2-carbaldehyde 在 platinum(II) chloride Chiraplak OD-H 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 4.33h， 生成 5-methyl-6-phenyl-1-tosyl-1,6-dihydropyridin-3-yl acetate
  参考文献：
  名称：

  Pt（II）从叠氮基炔丙基炔丙基酯催化合成1,2-二氢吡啶。

  摘要：

  Pt（II）催化的叠氮基炔丙基丙酸酯的环异构化反应可得到具有区域定义的取代基的1,2-二氢吡啶。已经证明了1，2-二氢吡啶向相应取代的吡啶的温和转化以及从叠氮基炔丙基炔丙基酯底物的手性保留。

  DOI：

  10.1021/ol070658i
• 作为产物：
  描述：

  chloroamine-T 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 2-methyl-3-phenyl-1-tosylaziridine-2-carbaldehyde
  参考文献：
  名称：

  Pt（II）从叠氮基炔丙基炔丙基酯催化合成1,2-二氢吡啶。

  摘要：

  Pt（II）催化的叠氮基炔丙基丙酸酯的环异构化反应可得到具有区域定义的取代基的1,2-二氢吡啶。已经证明了1，2-二氢吡啶向相应取代的吡啶的温和转化以及从叠氮基炔丙基炔丙基酯底物的手性保留。

  DOI：

  10.1021/ol070658i

文献信息

• Triazolium Carbene Catalysts and Stereoselective Bond Forming Reactions Thereof
  申请人：Rovis Tomislav

  公开号：US20110224431A1

  公开（公告）日：2011-09-15

  Provided herein are triazolium carbine catalysts useful for asymmetric hydration, fluorination, and deuteration, and processes for their preparation. Also provided are synthetic reactions in which these catalysts are used, in particular, in stereoselective formation of carbon-chlorine, carbon-hydrogen, carbon-fluorine, and carbon-deuterium bonds.

  本文提供了用于不对称水合、氟化和重氢化的三唑碳催化剂，以及它们的制备方法。还提供了在这些催化剂中使用的合成反应，特别是在碳-氯、碳-氢、碳-氟和碳-氘键的立体选择性形成中使用的反应。
• Catalytic Asymmetric Aziridination of α,β‐Unsaturated Aldehydes
  作者：Luca Deiana、Pawel Dziedzic、Gui‐Ling Zhao、Jan Vesely、Ismail Ibrahem、Ramon Rios、Junliang Sun、Armando Córdova

  DOI：10.1002/chem.201100042

  日期：2011.7.4

  highly enantioselective one‐pot cascade sequence based on the combination of asymmetric amine and N‐heterocyclic carbene catalysis (AHCC) is also disclosed. This one‐pot three‐component co‐catalytic transformation between α,β‐unsaturated aldehydes, hydroxylamine derivatives, and alcohols gives the corresponding N‐tert‐butoxycarbonyl and N‐carbobenzyloxy‐protected β‐amino acid esters with ee values ranging

  介绍了α，β-不饱和醛高度对映选择性有机催化叠氮化的发展，范围和应用。α，β-不饱和醛的氨基催化叠氮化使β-甲酰基氮丙啶的不对称形成率高达> 19：1 dr和99％  ee。α-单取代的烯醛的氨基催化叠氮化可以高产率和高达99％ee的速率接近末端α-取代-α-甲酰基氮丙啶 。对于双取代的α，β-不饱和醛的有机催化叠氮化，转化具有很高的非对映选择性和对映选择性，并得到几乎对映体纯的β-甲酰基官能化氮丙啶产品（99％  ee）。还公开了基于不对称胺和N-杂环卡宾催化（AHCC）结合的高度对映选择性单锅级联序列。α，β不饱和醛，羟胺衍生物，和醇之间这种一锅三组分共催化转化得到相应的Ñ -叔丁氧羰基和ñ -苄酯基保护的β氨基酸酯与EE值范围从92- 99％。还讨论了所有这些催化转化的机理和立体化学。
• Nucleophilic Carbene and HOAt Relay Catalysis in an Amide Bond Coupling:  An Orthogonal Peptide Bond Forming Reaction
  作者：Harit U. Vora、Tomislav Rovis

  DOI：10.1021/ja0764052

  日期：2007.11.1

  A catalyzed internal redox process provides a route from alpha-reducible aldehydes and amines; to alpha-reduced amides. The chemistry is catalyzed by nucleophilic carbenes and common peptide cocatalysts such as HOBt and HOAt in a relay fashion. The transformation proceeds in excellent yields using a variety of primary and secondary alkyl and aryl amines. The aldehyde component may be varied from haloaldehydes to epoxy and aziridino aldehydes as well as enals. The latter three substrates provide for a waste-free amide bond forming reaction.
• Tetrasubstituted Pyrrolidines via a Tandem Aza-Payne/Hydroamination Reaction
  作者：Jennifer M. Schomaker、Andrea R. Geiser、Rui Huang、Babak Borhan

  DOI：10.1021/ja068077w

  日期：2007.4.1

  A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination.
• 3,4-Dihydroxypyrrolidines via Modified Tandem Aza-Payne/Hydroamination Pathway
  作者：Aman Kulshrestha、Nastaran Salehi Marzijarani、Kumar Dilip Ashtekar、Richard Staples、Babak Borhan

  DOI：10.1021/ol301204w

  日期：2012.7.20

  The outcome of a tandem aza-Payne/hydroamination reaction is modified via the use of a latent nucleophile. The latter initially serves as an electrophile to intercept the aziridine alkoxide and afterward turns into a nucleophile thereby performing the aziridine ring opening, out competing the intramolecular aza-Payne pathway. Subsequent hydroamination in the same pot provides N-Ts enamide carbonates, which can be easily converted into biologically significant 3,4-dihydroxylactams.