N-(4-methylphenylsulfonyl)-2-<(phenylmethoxy)methyl>aziridine | 223905-86-0

• 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: N-(4-methylphenylsulfonyl)-2-<(phenylmethoxy)methyl>aziridine
• 英文别名: 2-((benzyloxy)methyl)-1-tosylaziridine；1-(4-Methylphenyl)sulfonyl-2-(phenylmethoxymethyl)aziridine
• CAS: 223905-86-0
• 化学式: C₁₇H₁₉NO₃S
• 分子量: 317.409
• InChiKey: ZOWVIHCXRWBJAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 N-(4-methylphenylsulfonyl)-2-<(phenylmethoxy)methyl>aziridine 在 三乙胺 作用下， 以 硝基甲烷 为溶剂， 反应 6.0h， 以90%的产率得到4-[(benzyloxy)methyl]-3-tosylthiazolidine-2-thione
  参考文献：
  名称：

  功能化的1,3-氧杂硫杂环戊烷和1,3-噻唑烷的有机催化一锅合成

  摘要：

  摘要报道了一种用于合成1，3-氧杂硫杂环戊烷和1，3-噻唑烷的有效有机催化方法。在这种方法中，硝基甲烷的共轭碱被用作潜在的有机催化剂，以促进环境条件下应变杂环化合物与杂多烯之间的环化反应。 图形概要

  DOI：

  10.1007/s00706-015-1543-3
• 作为产物：
  描述：

  (S)-苄氧甲基环氧乙烷 在 吡啶 、 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 N-(4-methylphenylsulfonyl)-2-<(phenylmethoxy)methyl>aziridine
  参考文献：
  名称：

  在固液PTC条件下通过环氧化物的区域选择性开环合成N-磺酰基氮丙啶

  摘要：

  在固体-液相转移催化（SL-PTC）条件下，环氧化物1与4-甲苯磺酰胺（6）的开环以高产率提供了区域选择性的β-磺酰胺基醇7。在羟基离去基团活化后，将它们进一步转化为N-磺酰基氮丙啶9，然后在碳酸钾存在下闭环。

  DOI：

  10.1016/s0040-4020(99)00214-8

文献信息

• Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy
  作者：Guangyin Qian、Miao Bai、Shijun Gao、Han Chen、Siwei Zhou、Hong-Gang Cheng、Wei Yan、Qianghui Zhou

  DOI：10.1002/anie.201806780

  日期：2018.8.20

  Reported is a modular one‐step three‐component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza‐Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking

  报告的是使用Catellani策略的模块化一步法三组分合成四氢异喹啉。该过程通过钯/降冰片烯协同催化，利用氮丙啶作为烷基化试剂，从而实现Catellani / Heck / Aza-Michael加成级联反应。这种温和，化学选择性和可扩展的方案具有广泛的底物范围（43个实例，产率高达90％）。该方案最引人注目的功能是观察到的2-烷基和2-芳基取代的氮丙啶分别具有1,3-顺式取代和1,4-顺式取代的四氢异喹啉类的优异的区域选择性和非对映选择性。而且，这是具有高步骤和原子经济性的通用方法。
• Synthesis of Hexahydro-1<i>H</i>-benzo[<i>c</i>]chromen-1-amines via the Intramolecular Ring-Opening Reactions of Aziridines by π-Nucleophiles
  作者：Stephen Bergmeier、Aravinda Pulipaka

  DOI：10.1055/s-2008-1072561

  日期：2008.5

  The intramolecular cyclization of aziridines with π-nucleophiles can be a useful route to a number of heterocyclic and carbocyclic systems. This methodology has been applied to the synthesis of hexahydro-1H-benzo[c]chromen-1-amines, the basic skeleton of many amaryllidaceae alkaloids. The success of the aziridine cyclization is largely dependent on the N-substitution of aziridine, with activated aziridines not undergoing the cyclization reaction. Only N-H-, N-alkyl- and N-arylaziridines underwent the cyclization reaction. The ring opening of an unactivated aziridines with a π-nucleophile is one of the first examples of such a reaction.

  氮丙啶与 Ï-nucleophiles 的分子内环化反应是获得许多杂环和碳环系统的有用途径。这种方法已被应用于合成六氢-1H-苯并[c]色烯-1-胺（许多金盏花科生物碱的基本骨架）。氮丙啶环化反应的成功在很大程度上取决于氮丙啶的 N-取代，活化的氮丙啶不会发生环化反应。只有 N-H、N-烷基和 N-芳基氮丙啶发生了环化反应。未活化的氮丙啶与Ï-亲核物的开环反应是此类反应的首例之一。
• Pentacoordinate Organoaluminum Chemistry:  Catalytic Efficiency of Me₃Al in the Epoxide Cleavage with Alkynyllithiums
  作者：Takashi Ooi、Naoko Kagoshima、Hayato Ichikawa、Keiji Maruoka

  DOI：10.1021/ja9842464

  日期：1999.4.1

  A new and highly effective catalytic method for epoxide alkynylations has been developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoalluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (l-benzyloxy)-3-butene oxide (1), in toluene with PhC=CLi under the influence of catalytic Me3Al (10 mol%) proceeded smoothly at O degrees C for 5 h to furnish the alkynylation product, l-(benzyloxy)-6-phenylhex-5-yn-3-ol, in 76% yield [cf. 3% without Me3Al catalyst; 78% with stoichiometric Me3Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me3Al complexes of epoxy ethers of type 1 is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-l-pentene oxide, which was not susceptible to nucleophile attack of PhC=CLi with catalytic Me3A1 under similar conditions. The pentacoordinate complex formation of Me3Al with epoxy ether 1 is characterized by low-temperature C-13 and Al-27 NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alcohol synthesis.
• Development of a [3+3] approach to tetrahydropyridines and its application in indolizidine alkaloid synthesis
  作者：Lisa C. Pattenden、Harry Adams、Stephen A. Smith、Joseph P.A. Harrity

  DOI：10.1016/j.tet.2008.01.071

  日期：2008.3

  A stepwise [3+3] annelation sequence is described that generates tetrahydropyridines from the corresponding aziridines. The scope of this process is described and its potential for the stereoselective synthesis of indolizidines is highlighted by the synthesis of (-)-monomorine. (C) 2008 Elsevier Ltd. All rights reserved.
• CN115260096
  申请人：——

  公开号：——

  公开（公告）日：——