3-(Phenylthio)-2-piperidone | 104261-03-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(Phenylthio)-2-piperidone
• 英文别名: 3-(phenylthio)piperidin-2-one；3-phenylsulfanylpiperidin-2-one
• CAS: 104261-03-2
• 化学式: C₁₁H₁₃NOS
• 分子量: 207.296
• InChiKey: PFQWCMOJVWDVMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(Phenylthio)-2-piperidone 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-cinnamoyl-5,6-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  Activity-based protein profiling reveals GSTO1 as the covalent target of piperlongumine and a promising target for combination therapy for cancer

  摘要：

  通过ABPP，已确定piperlongumine通过共价结合和抑制GSTO1诱导癌细胞死亡，并与其他抗癌药物具有广谱协同作用。

  DOI：

  10.1039/c9cc00917e
• 作为产物：
  描述：

  1-(methoxymethyl)piperidin-2-one 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 6.75h， 生成 3-(Phenylthio)-2-piperidone
  参考文献：
  名称：

  Activity-based protein profiling reveals GSTO1 as the covalent target of piperlongumine and a promising target for combination therapy for cancer

  摘要：

  通过ABPP，已确定piperlongumine通过共价结合和抑制GSTO1诱导癌细胞死亡，并与其他抗癌药物具有广谱协同作用。

  DOI：

  10.1039/c9cc00917e

文献信息

• Inter- and Intraspecific Comparisons of Antiherbivore Defenses in Three Species of Rainforest Understory Shrubs
  作者：R. M. Fincher、L. A. Dyer、C. D. Dodson、J. L. Richards、M. A. Tobler、J. Searcy、J. E. Mather、A. J. Reid、J. S. Rolig、W. Pidcock

  DOI：10.1007/s10886-008-9432-4

  日期：2008.4

  Plants defend themselves against herbivores and pathogens with a suite of morphological, phenological, biochemical, and biotic defenses, each of which is presumably costly. The best studied are allocation costs that involve trade-offs in investment of resources to defense versus other plant functions. Decreases in growth or reproductive effort are the costs most often associated with antiherbivore defenses, but trade-offs among different defenses may also occur within a single plant species. We examined trade-offs among defenses in closely related tropical rain forest shrubs (Piper cenocladum, P. imperiale, and P. melanocladum) that possess different combinations of three types of defense: ant mutualists, secondary compounds, and leaf toughness. We also examined the effectiveness of different defenses and suites of defenses against the most abundant generalist and specialist Piper herbivores. For all species examined, leaf toughness was the most effective defense, with the toughest species, P. melanocladum, receiving the lowest incidence of total herbivory, and the least tough species, P. imperiale, receiving the highest incidence. Although variation in toughness within each species was substantial, there were no intraspecific relationships between toughness and herbivory. In other Piper studies, chemical and biotic defenses had strong intraspecific negative correlations with herbivory. A wide variety of defensive mechanisms was quantified in the three Piper species studied, ranging from low concentrations of chemical defenses in P. imperiale to a complex suite of defenses in P. cenocladum that includes ant mutualists, secondary metabolites, and moderate toughness. Ecological costs were evident for the array of defensive mechanisms within these Piper species, and the differences in defensive strategies among species may represent evolutionary trade-offs between costly defenses.

  植物通过一系列形态、生态、化学和生物防御来抵御食草动物和病原体，每种防御机制都 presumably 伴随着一定的成本。最常研究的是分配成本，即在防御和植物其他功能之间进行资源投资的权衡。与抗食草防御最常相关的成本是生长或繁殖努力的减少，但同一植物物种内部不同防御机制之间也可能存在权衡。我们研究了三种具有不同防御组合的密切相关的热带雨林灌木（Piper cenocladum、P. imperiale 和 P. melanocladum）之间的防御权衡，这些防御包括：蚂蚁共生、次生化合物和叶片韧性。我们还考察了不同防御及其组合对最常见的广义和专一的 Piper 食草动物的有效性。对于所有研究的物种，叶片韧性是最有效的防御，最韧性强的物种 P. melanocladum 遭受总食草损害的发生率最低，而韧性最弱的物种 P. imperiale 的发生率最高。尽管每种物种内部韧性的变化显著，但韧性与食草之间没有种内关系。在其他 Piper 研究中，化学和生物防御与食草之间存在显著的种内负相关。在研究的三种 Piper 物种中，量化了多种防御机制，从 P. imperiale 的低浓度化学防御到 P. cenocladum 的复杂防御组合，后者包括蚂蚁共生、次生代谢物和中等韧性。生态成本在这些 Piper 物种的防御机制中显而易见，物种之间防御策略的差异可能代表了在昂贵防御之间的进化权衡。
• REGIOSELECTIVE SULFENYLATION OF OXIME DIANIONS. A NOVEL AND USEFUL METHOD FOR THE REGIOSELECTIVE RING CLEAVAGE
  作者：Kunio Hiroi、Masahiko Otsuka、Shuko Sato

  DOI：10.1246/cl.1985.1907

  日期：1985.12.5

  Treatment of the dianions of cyclic ketoximes with diphenyl disulfide underwent a regioselective sulfenylation at the syn α-carbons. Regioselective alkylation of cyclic ketoxime dianions, followed by sulfenylation with diphenyl disulfide, produced α-alkyl-α′-phenylsulfenyl ketoximes. A Beckmann fragmentation of these sulfenylated ketoximes gave ring cleaved products. This procedure provides a synthetically

  用二苯基二硫化物处理环状酮肟的二价阴离子在顺α-碳上发生区域选择性亚磺酰化。环状酮肟双阴离子的区域选择性烷基化，然后用二苯基二硫化物进行亚磺酰化，产生 α-烷基-α'-苯基亚磺酰基酮肟。这些磺基化酮肟的贝克曼断裂得到环裂解产物。该过程为区域选择性环裂解提供了一种综合有用的方法，保留了有价值的功能。
• Diels-Alder reactions of dihydropyridinones: synthetic entry to the manzamine A tricyclic core
  作者：Yasuhiro Torisawa、Masako Nakagawa、Toshihiro Hosaka、Kiyoshi Tanabe、Ziping Lai、Koreharu Ogata、Tadashi Nakata、Takeshi Oishi、Tohru Hino

  DOI：10.1021/jo00047a031

  日期：1992.10

  For the construction of the tricyclic core of manzamine A (1), the Diels-Alder reactions of some dihydropyridinones were surveyed. The N-protecting group of the dihydropyridinone played an important role in achieving a successful Diels-Alder reaction. In view of its electron-withdrawing character as well as its thermal stability, the p-toluenesulfonyl protecting group was found to be best in our synthesis. An effective method for the preparation of 3-alkyldihydropyridinones via the Michael addition to dehydroalanine derivatives has also been devised. By the utilization of a high-pressure Diels-Alder reaction of the N-tosyl-3-alkyldihydropyridinone (17) with the Danishefsky diene, a facile construction of the central pyrroloisoquinoline skeleton (21) was successfully achieved.
• Torisawa, Yasuhiro; Nakagawa, Masako; Takami, Hideo, Heterocycles, 1994, vol. 39, # 1, p. 277 - 292
  作者：Torisawa, Yasuhiro、Nakagawa, Masako、Takami, Hideo、Nagata, Toshiaki、Ali, Mohamed Ayman、et al.

  DOI：——

  日期：——
• HIROI, KUNIO;OTSUKA, MASAHIKO;SATO, SHUKO, CHEM. LETT., 1985, N 12, 1907-1910
  作者：HIROI, KUNIO、OTSUKA, MASAHIKO、SATO, SHUKO

  DOI：——

  日期：——