N-(4-methylphenyl)sulfonyl-3-phenylaziridin-2-ylmethanol | 167254-90-2

• 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-methylphenyl)sulfonyl-3-phenylaziridin-2-ylmethanol
• 英文别名: (2R,3S)-1-(4-methylphenyl)sulfonyl-3-phenyl-aziridinemethanol；[(2R,3S)-1-(4-methylphenyl)sulfonyl-3-phenylaziridin-2-yl]methanol
• CAS: 167254-90-2
• 化学式: C₁₆H₁₇NO₃S
• 分子量: 303.382
• InChiKey: XDRLCBVFGRIVHH-PYNWJHIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methylphenyl)sulfonyl-3-phenylaziridin-2-ylmethanol 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2R,3S)-3-Phenyl-1-(toluene-4-sulfonyl)-aziridine-2-carbaldehyde
  参考文献：
  名称：

  Fujii, Nobutaka; Nakai, Kazuo; Tamamura, Hirokazu, Journal of the Chemical Society. Perkin transactions I, 1995, # 11, p. 1359 - 1372

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3S)-2-(tert-butyldimethylsiloxy)methyl-1-(4-methylphenyl)sulfonyl-3-phenylaziridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到N-(4-methylphenyl)sulfonyl-3-phenylaziridin-2-ylmethanol
  参考文献：
  名称：

  Synthesis of Optically Pure 2-Aziridinemethanols: Versatile Synthetic Building Blocks.

  摘要：

  介绍了从(S)-苏氨酸、(R)-全苏氨酸、手性 2-氨基醇或对映体富集的 2，3-环氧醇出发，合成三对顺反异构的 N-磺酰基-2-氮丙啶甲醇。此外，还介绍了从(R)-和(S)-丝氨酸合成 N-对甲基苯磺酰-和 N-甲磺酰-2-氮丙啶甲醇的合成路线。

  DOI：

  10.1248/cpb.42.2241

文献信息

• An aza-Payne rearrangement-epoxide ring opening reaction of 2-aziridinemethanols in a one-pot manner: A regio- and stereoselective synthetic route to diastereomerically pure N-protected 1,2-amino alcohols
  作者：Toshiro Ibuka、Kazuo Nakai、Masako Akaji、Hirokazu Tamamura、Nobutaka Fujii、Yoshinori Yamamoto

  DOI：10.1016/0040-4020(96)00682-5

  日期：1996.9

  A regio- and stereoselective synthetic route to diastereomerically pure 1,2-amino alcohols via a one-pot aza-Payne rearrangement - epoxide ring opening reaction of 2-aziridinemethanols is reported.

  据报道，通过一锅氮杂-佩因重排-2-氮丙啶甲醇的环氧化物开环反应，制得非对映体纯的1,2-氨基醇的区域和立体选择性合成路线。
• A one-pot aza-Payne rearrangement-epoxide ring opening reaction of 2-aziridinemethanols: A regio- and stereoselective synthetic route to diastereomerically pure 1,2-amino alcohols
  作者：Kazuo Nakai、Toshiro Ibuka、Akira Otaka、Hirokazu Tamamura、Nobutaka Fujii、Yoshinori Yamamoto

  DOI：10.1016/0040-4039(95)01203-t

  日期：1995.8

  A regio- and stereoselective synthetic route to diastereomerically pure 1,2-amino alcohols via a one-pot aza-Payne rearrangement — epoxide ring opening reaction of 2-aziridinemethanols is reported. Satisfactory yields are obtained in excellent diastereoisomeric excesses by successive exposure of 2-aziridinemethanols to potassium hydride and nucleophilic reagents in a one-pot manner.

  据报道，通过一锅氮杂-佩因重排（2-氮丙啶甲醇的环氧化物开环反应）制得非对映体纯的1,2-氨基醇的区域和立体选择性合成路线。通过以一锅方式将2-氮丙啶甲醇连续暴露于氢化钾和亲核试剂中，可获得极好的非对映异构体过量的令人满意的收率。
• Kinetic Resolution of <i>trans</i>-2,3-Aziridinyl Alcohols via Hydroxyl Directed Regio- and Enantioselective Ring Opening Reactions
  作者：Zhe-Ran Chang、Si-Si Du、Cui Zhang、Shuang-Hu Chen、Yuan-Zhao Hua、Min-Can Wang、Guang-Jian Mei、Shi-Kun Jia

  DOI：10.1021/acscatal.3c01252

  日期：2023.5.19

  An efficient kinetic resolution of racemic trans-2,3-aziridinyl alcohols is established via zinc catalyzed ring opening reactions with various amines as the nucleophiles. The directing effect of the hydroxyl group and the precise enantiodiscrimination by dinuclear zinc cooperative catalyst are the keys to success of high regioselectivity and enantioselectivity. A range of enantioenriched vicinal diamines

  通过以各种胺作为亲核试剂的锌催化开环反应，建立了外消旋反式-2,3-氮丙啶醇的有效动力学拆分。羟基的导向作用和双核锌协同催化剂的精确对映区分是高区域选择性和对映选择性成功的关键。一系列对映体富集的邻位二胺和反式-2,3-氮丙啶醇以良好的产率和优异的 ee 值获得。据我们所知，这是 2,3-氮丙啶醇的定向对映选择性亲核开环反应的第一个例子。
• Aza-Payne Rearrangement of Activated 2-Aziridinemethanols and 2,3-Epoxy Amines under Basic Conditions
  作者：Toshiro Ibuka、Kazuo Nakai、Hiromu Habashita、Yuka Hotta、Akira Otaka、Hirokazu Tamamura、Nobutaka Fujii、Norio Mimura、Yoshihisa Miwa、Yukiyasu Chounan、Yoshinori Yamamoto

  DOI：10.1021/jo00112a028

  日期：1995.4

  An aza-Payne rearrangement of activated 2-aziridinemethanols with t-BuOK, NaH, or KH at near 0 degrees C in common solvents such as THF, toluene, 1,2-dimethoxyethane, 1,4-dioxane, or a mixed solvent of THF-HMPA followed by quenching at -78 degrees C gives the corresponding epoxysulfonamides. Exposure of N-tosyl-(2S)-azetidinemethanol (36) and N-tosyl-(S)-prolinol (37) to NaH or KH in dichloromethane yielded only the respective dimeric compounds that resulted by joining 2 equiv of reactant through a methylene group. Reaction of N-tosyl-(2S,3S)-3-methyl-2-aziridinemethanol (9) and its (2R,3S)-isomer 23 with Gilman reagents (R(2)CuLi; R = Me and Bu) or ''higher order'' cuprates [R(2)Cu(CN)Li-2; R = Me and Bu] yielded the two expected aziridine ring-opening products. In sharp contrast, treatment of 9 and 23 with ''lower order'' cuprates afforded rearrangement-opened products. Thus, if the nucleophile is highly reactive, then the expected nucleophilic ring opening of the aziridine predominates. However, if the nucleophile is less reactive, then it becomes possible to cleave the resulting rearranged epoxide. Upon exposure of 2,3-epoxy amines to an equimolar mixture of t-BuOK-n-BuLi in a mixed solvent of THF and n-hexane at -78 degrees C, the equilibrium lies exclusively toward the hydroxy aziridine forming direction.
• US5929252A
  申请人：——

  公开号：US5929252A

  公开（公告）日：1999-07-27