(2R,3S)-3-methyl-1-<(4-methylphenyl)sulfonyl>-2-azidirinemethanol | 153829-45-9

• 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: (2R,3S)-3-methyl-1-<(4-methylphenyl)sulfonyl>-2-azidirinemethanol
• 英文别名: [(2R,3S)-3-methyl-1-(4-methylphenyl)sulfonylaziridin-2-yl]methanol
• CAS: 153829-45-9
• 化学式: C₁₁H₁₅NO₃S
• 分子量: 241.311
• InChiKey: DSUQRBHLWFVFKB-HFLPBZFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (2R,3S)-3-methyl-1-<(4-methylphenyl)sulfonyl>-2-azidirinemethanol 在 sodium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 18.0h， 以87%的产率得到4-Methyl-N-((S)-(S)-1-oxiranyl-ethyl)-benzenesulfonamide
  参考文献：
  名称：

  2-氮丙啶甲醇与“低级”甲基氰尿酸锂的空前重排反应

  摘要：

  可以通过使用吉尔曼试剂或低级氰尿酸酯在2-氮丙啶甲醇的开环反应中实现互补的选择性。在前一种情况下，吉尔曼试剂对底物1和2的通常攻击导致分别形成了预期的开环产物（3和4）和（7和8）。相反，将1和2都暴露于低级氰铜酸盐中却以前所未有的方式进行，大概是通过环氧化物D和G来生成意想不到的仲醇（11和12）作为主要产品。

  DOI：

  10.1016/s0040-4039(00)60142-9
• 作为产物：
  描述：

  (2R,3S)-2-(tert-butyldimethylsiloxy)methyl-3-methyl-1-<(4-methylphenyl)sulfonyl>aziridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以95%的产率得到(2R,3S)-3-methyl-1-<(4-methylphenyl)sulfonyl>-2-azidirinemethanol
  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

• Unprecedented rearrangement reaction of 2-aziridinemethanols with “lower order” lithium methylcyanocuprate
  作者：Toshiro Ibuka、Kazuo Nakai、Hiromu Habashita、Nobutaka Fujii、Fabrice Garrido、André Mann、Yukiyasu Chounan、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(00)60142-9

  日期：1993.11

  Complementary selectivity can be achieved in ring opening reactions of 2-aziridinemethanols by using either the Gilman reagent or lower order cyanocuprate. In the former case, the usual attack of the Gilman reagent to the substrates 1 and 2 results in the formation of the expected ring opening products (3 and 4) and (7 and 8), respectively. In contrast, exposure of both 1 and 2 to the lower order cyanocuprate

  可以通过使用吉尔曼试剂或低级氰尿酸酯在2-氮丙啶甲醇的开环反应中实现互补的选择性。在前一种情况下，吉尔曼试剂对底物1和2的通常攻击导致分别形成了预期的开环产物（3和4）和（7和8）。相反，将1和2都暴露于低级氰铜酸盐中却以前所未有的方式进行，大概是通过环氧化物D和G来生成意想不到的仲醇（11和12）作为主要产品。
• 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。
• 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.
• Synthesis of Optically Pure 2-Aziridinemethanols: Versatile Synthetic Building Blocks.
  作者：Nobutaka FUJII、Kazuo NAKAI、Hiromu HABASHITA、Yuka HOTTA、Hirokazu TAMAMURA、Akira OTAKA、Toshiro IBUKA

  DOI：10.1248/cpb.42.2241

  日期：——

  Synthesis of three cis-trans pairs of N-sulfonylated-2-aziridinemethanols starting from (S)-threonine, (R)-allothreonine, a chiral 2-amino alcohol, or enantiomerically enriched 2, 3-epoxy alcohols is described. A synthetic route to N-tosyl- and N-mesyl-2-aziridinemethanols from (R)- and (S)-serines is also presented.

  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。