(-)-(R_S)-2-methyl-N-(pent-4-en-1-ylidene)propane-2-sulfinamide | 943231-75-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (-)-(R_S)-2-methyl-N-(pent-4-en-1-ylidene)propane-2-sulfinamide
• 英文别名: (NE,R)-2-methyl-N-pent-4-enylidenepropane-2-sulfinamide
• CAS: 943231-75-2
• 化学式: C₉H₁₇NOS
• 分子量: 187.306
• InChiKey: HYTHKJWBSJYOCY-ZJNQMXKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(R_S)-2-methyl-N-(pent-4-en-1-ylidene)propane-2-sulfinamide 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.83h， 生成
  参考文献：
  名称：

  Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction:  An Easy Entry to Cyclic β-Amino Carbonyl Derivatives

  摘要：

  Hoveyda-Grubbs catalyst in combination with BF3 center dot OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of beta-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched alpha-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process.

  DOI：

  10.1021/ja0709829
• 作为产物：
  描述：

  4-戊烯醛 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以71%的产率得到(-)-(R_S)-2-methyl-N-(pent-4-en-1-ylidene)propane-2-sulfinamide
  参考文献：
  名称：

  Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction:  An Easy Entry to Cyclic β-Amino Carbonyl Derivatives

  摘要：

  Hoveyda-Grubbs catalyst in combination with BF3 center dot OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of beta-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched alpha-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process.

  DOI：

  10.1021/ja0709829

文献信息

• Convergent and Modular Synthesis of Candidate Precolibactins. Structural Revision of Precolibactin A
  作者：Alan R. Healy、Maria I. Vizcaino、Jason M. Crawford、Seth B. Herzon

  DOI：10.1021/jacs.6b02276

  日期：2016.4.27

  Escherichia coli. The metabolites are encoded by the clb gene cluster as prodrugs termed precolibactins. clb(+) E. coli induce DNA double-strand breaks in mammalian cells in vitro and in vivo and are found in 55-67% of colorectal cancer patients, suggesting that mature colibactins could initiate tumorigenesis. However, elucidation of their structures has been an arduous task as the metabolites are obtained

  大肠杆菌素是由某些共生和肠外致病性大肠杆菌菌株产生的混合聚酮化合物-非核糖体肽天然产物。代谢物由 clb 基因簇编码，称为前体药物。clb(+) 大肠杆菌在体外和体内诱导哺乳动物细胞 DNA 双链断裂，并且在 55-67% 的结肠直肠癌患者中发现，表明成熟的大肠杆菌素可以引发肿瘤发生。然而，阐明它们的结构一直是一项艰巨的任务，因为从细菌培养物中获得的代谢物数量极少 (μg/L)，并且被认为是不稳定的。在此，我们描述了一种灵活且收敛的合成路线来制备先进的前大肠杆菌素和衍生物。合成通过两个复杂前体（例如，28 + 17 → 29a，90%），然后是碱诱导的双脱水级联反应，形成两个目标环（例如，29a → 30a，79%）。该序列提供了超过发酵获得的数量的先进候选前大肠杆菌素的数量，并且预计可以很容易地进行缩放。这些研究指导了预测代谢物 precolibactin A（从 5a 或 5b 到 7）的结构修订，并证实了分离的代谢物