2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid | 97273-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苏丹
• 英文名称: 2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid
• 英文别名: 2-Cyclohexyl-3-phenylthiazetidine 1,1-dioxide
• CAS: 97273-03-5
• 化学式: C₁₄H₁₉NO₂S
• 分子量: 265.376
• InChiKey: WXPMKOQIEZJNHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid 在 三氯化铝 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 苯基-丙烯-2-磺酸酰胺
  参考文献：
  名称：

  Stereospecific C-N Bond Cleavage of 4-Silylated 1,2-Thiazetidine 1,1-Dioxides with EtAlCl2 or AlCl3: Formation of (E)-Vinylsulfonamides.

  摘要：

  将 1，2-噻嗪啶 1，1-二氧化物（β-舒坦类）3 单硅烷化后，可立体选择性地得到 (3R*，4S*)-4-单硅烷-β-舒坦类 4。使用三甲基氯硅烷可以得到二硅烷基化的 β-苏丹酰胺 5。用 EtAlCl2 处理 4-单硅烷基-β-苏丹酰胺 4 时，由于硅基的β阳离子稳定作用，C-N 键发生了立体特异性裂解，从而得到了(E)-乙烯基磺酰胺 (E)-7。(E)-α-硅烷磺酰胺 (E)-7j-l 是在 4，4-二硅烷-β-舒坦 5 与 EtAlCl2 的反应中生成的。4, 4-二硅烷基-β-舒坦与 AlCl3 反应生成 N-脱烷基的 (E)-乙烯基磺酰胺，产率良好。在四丁基氟化铵和 BF3-Et2O 存在下，(E)-α-硅烷基苯乙烯磺酰胺 (E)-10 与苯甲醛反应，得到烯丙基醇 (E)-12。

  DOI：

  10.1248/cpb.46.757
• 作为产物：
  描述：

  β-苯乙烯磺酰氯 在 sodium hydroxide 、 氯仿 、 水 、 三氯化磷 作用下， 以 水 、 三氯氧磷 为溶剂， 反应 80.0h， 生成 2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid
  参考文献：
  名称：

  Meyle, Eberhard; Keller, Egbert; Otto, Hans-Hartwig, Liebigs Annalen der Chemie, 1985, # 4, p. 802 - 812

  摘要：

  DOI：

文献信息

• Reactions of a β-sultam ring with Lewis acids via the CS bond cleavage
  作者：Tetsuo Iwama、Miyoko Ogawa、Tadashi Kataoka、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1016/s0040-4020(98)00510-9

  日期：1998.7

  Selective CS bond cleavage of a β-sultam ring was achieved by the reactions with Lewis acids. Aryl ketones or aldehyde were provided from 3-aryl-β-sultams whereas β-sultams bearing a poorly migratory substituent at C-3 gave trans-1,2,3-oxathiazolidine 2-oxides and/or cis-aziridines. These reactions were influenced by the cation-stabilizing capability of C-4 substituents and by the configuration of

  通过与路易斯酸的反应，实现了β-杜马环的选择性CS键裂解。由3-芳基-β-sultams提供芳基酮或醛，而在C-3处带有较差迁移性取代基的β-sultams提供反式-1,2,3-氧杂噻唑烷2-氧化物和/或顺式-氮丙啶。这些反应受C-4取代基的阳离子稳定能力以及C-3和C-4上取代基的构型的影响。某些4-烯基-3-芳基-β-sultams进行串联分子内环化反应，通过CS键断裂过程得到双环[3.2.1]-和[2.2.1]-γ-sultams ，1,2-芳基转移，阳离子-烯烃环化和磺酰基阴离子的重组。
• Preparation of Sulfonamides from Sodium Sulfonates: Ph3P ⋅ Br2 and Ph3P ⋅ Cl2 as a Mild Halogenating Reagent for Sulfonyl Bromides and Sulfonyl Chlorides
  作者：Tadashi Kataoka、Tetsuo Iwama、Tomofumi Setta、Atsuko Takagi

  DOI：10.1055/s-1998-4488

  日期：1998.4

  Arene- and alkanesulfonamides were prepared by treatment of the corresponding sodium sulfonates with triphenylphosphine dibromide or dichloride followed by amines in the presence of triethylamine via sulfonyl halides. Reactions of sodium aminosulfonates gave cyclized products. Amidation of p-toluenesulfonic acid with triphenylphosphine dichloride was also examined to give N-benzyl-p-toluenesulfonamide. Methyl p-toluenesulfonate was obtained by esterification of sodium p-toluenesulfonate via p-toluenesulfonyl chloride.

  通过在三乙胺存在下，将相应的磺酸钠与三苯基膦二溴化物或二氯化物反应生成磺酰卤，随后与胺反应，制备了芳基磺酰胺和烷基磺酰胺。氨基磺酸钠的反应得到了环化产物。还研究了使用三苯基膦二氯化物与对甲苯磺酸的胺化反应，生成了N-苄基对甲苯磺酰胺。通过将对甲苯磺酰氯与对甲苯磺酸钠酯化，得到了甲基对甲苯磺酸酯。
• Reactions of 1,2-thiazetidine 1,1-dioxides with organometallics: β-Elimination and NS bond cleavage
  作者：Tetsuo Iwama、Tadashi Kataoka、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1016/s0040-4020(98)00239-7

  日期：1998.5

  Reactions of 4-nonsubstituted β-sultams 1 with methyllithium gave only (E)-vinylsulfonamides2, whereas 2-aminoethyl sulfones 3 were obtained as minor products by use of methylmagnesium bromide. Reactions of 4-monosubstituted β-sultams 6 with organolithiums gave (E)-vinylsulfonamides 7 stereoselectively regardless of the configuration of 3- and 4-substituents. Treatment of 4,4-dimethyl-β-sultam 8a with

  的反应4-未取代的β-磺内酰胺1与甲基仅给出（ë）-vinylsulfonamides 2，而-2氨乙基砜3通过使用甲基溴化镁得到次要产物。的4-单取代反应β-磺内酰胺6与有机锂，得到（É）-vinylsulfonamides 7立体选择性地不论3-和4-取代基的构型。4,4-二甲基β-磺内酰胺的治疗8A用甲基溴化镁和甲基锂提供2-氨基乙基砜9和双砜10，分别和异丙基苯基砜11 通过使用苯基锂或苯基溴化镁获得。
• Selective CS bond cleavage of 3-aryl-β-sultams with EtAlCl2
  作者：Ta-i Kataoka、Tetsuo Iwama

  DOI：10.1016/0040-4039(94)02183-c

  日期：1995.1

  Selective C-S bond cleavage of a beta-sultam ring was achieved by the reactions of 3-aryl-beta-sultams 1 with EtAlCl(2). Aryl ketones 2 or aldehyde 3 were provided via processes of the C-S bond cleavage, 1,2-aryl shift and imine formation. These reactions were influenced by the cation stabilizing capability of C-4 substituents and by the configuration of the substituents at C-3 and C-4.
• A New Synthesis of α-Amino Acid Thioesters by Pummerer Reaction of 3-Substituted-4-sulfinyl-β-sultams
  作者：Tetsuo Iwama、Tadashi Kataoka、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1021/jo981230n

  日期：1998.11.1

  alpha-Amino acid thioesters were synthesized by the Pummerer reaction of 3-substituted-4-sulfinyl-beta-sultams with TFAA. The 3-substituted-4-sulfinyl-beta-sultams were prepared from the corresponding beta-sultams by sulfenylation with diphenyl disulfide followed by m-CPBA oxidation. Diastereoselective synthesis of beta-sultams by 1,3-asymmetric induction in [2 + 2] cycloaddition of a sulfene intermediate and chiral imines in solution-phase was studied, and it was found that N-alkylimines gave better diastereoselectivities than N-aralkylimines. The use of imines derived from (R)- and (S)-alpha-methylbenzylamine followed by separation of the major and minor diastereomers gave enantiopure 3-substituted-N-methylbenzyl-beta-sultams. These beta-sultams were then converted to N-methylbenzyl-alpha-amino acid thioesters via sulfenylation and Pummerer rearrangement with high or complete retention of configuration.