(2S,3S)-2-methyl-1-(4-methylphenyl)sulfonyl-3-phenylazetidin-3-ol | 331000-11-4

• 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: (2S,3S)-2-methyl-1-(4-methylphenyl)sulfonyl-3-phenylazetidin-3-ol
• CAS: 331000-11-4
• 化学式: C₁₇H₁₉NO₃S
• 分子量: 317.409
• InChiKey: AQBILCYZCIMWEM-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-methyl-1-(4-methylphenyl)sulfonyl-3-phenylazetidin-3-ol 在 (S)-联萘(3,5-二甲苯基)膦 、 [Rh(OH)(cod)]2 作用下， 以 甲苯 为溶剂， 以99%的产率得到(3S,4S)-2,3,6-trimethyl-1,1-dioxo-4-phenyl-3H-1lambda6,2-benzothiazin-4-ol
  参考文献：
  名称：

  1,5-Rhodium Shift in Rearrangement ofN-Arenesulfonylazetidin-3-ols into Benzosultams

  摘要：

  Benzosultams are synthesized in an enantiopure form starting from alpha-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by beta-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.

  DOI：

  10.1021/ja410910s
• 作为产物：
  描述：

  N-Tosyl-L-alanine diazomethyl ketone 在 copper(II) acetate monohydrate 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 0.02h， 生成 (2S,3S)-2-methyl-1-(4-methylphenyl)sulfonyl-3-phenylazetidin-3-ol
  参考文献：
  名称：

  1,5-Rhodium Shift in Rearrangement ofN-Arenesulfonylazetidin-3-ols into Benzosultams

  摘要：

  Benzosultams are synthesized in an enantiopure form starting from alpha-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by beta-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.

  DOI：

  10.1021/ja410910s

文献信息

• 10.3762/bjoc.20.148
  作者：Maag, Henning、Lemcke, Daniel J.、Wahl, Johannes M.

  DOI：10.3762/bjoc.20.148

  日期：——

  are identified as promising building blocks for the synthesis of highly substituted dioxolanes. The presented strategy is founded on the build and release of molecular strain and achieves a formal transposition of a methyl group. During light irradiation, 3-phenylazetidinols are forged as reaction intermediates, which readily undergo ring opening upon the addition of electron-deficient ketones or boronic

   抽象的 α-氨基苯乙酮被认为是合成高度取代的二氧戊环的有前途的构建单元。所提出的策略建立在分子应变的构建和释放的基础上，并实现了甲基的正式转位。在光照射过程中，3-苯基氮杂环丁醇作为反应中间体形成，在添加缺电子酮或硼酸时很容易发生开环。这一两步过程成功开发的关键是二苯甲基保护基团的识别，该保护基团协调光化学诺里什-杨环化并促进随后的开环。 Beilstein J. Org. Chem. 2024, 20, 1671–1676. doi:10.3762/bjoc.20.148
• 1,5-Rhodium Shift in Rearrangement of<i>N</i>-Arenesulfonylazetidin-3-ols into Benzosultams
  作者：Naoki Ishida、Yasuhiro Shimamoto、Takaaki Yano、Masahiro Murakami

  DOI：10.1021/ja410910s

  日期：2013.12.26

  Benzosultams are synthesized in an enantiopure form starting from alpha-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by beta-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.