3-(methylthio)propanal oxime | 70569-52-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(methylthio)propanal oxime
• 英文别名: 3-Methylthiopropanaldoxime；N-(3-methylsulfanylpropylidene)hydroxylamine
• CAS: 70569-52-7
• 化学式: C₄H₉NOS
• 分子量: 119.188
• InChiKey: HVONYXQHMDPJKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(methylthio)propanal oxime 在 亚膦酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以34.6%的产率得到[1-(R,S)-amino-3-(methylsulphanyl)propyl]phosphinic acid
  参考文献：
  名称：

  含硫氨基酸次膦酸类似物的合成

  摘要：

  合成了蛋氨酸代谢的关键化合物的膦类似物。所得化合物在次膦基或含硫片段处被选择性氧化。

  DOI：

  10.1007/bf02495302
• 作为产物：
  描述：

  3-甲硫基丙醛 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 反应 14.0h， 以80%的产率得到3-(methylthio)propanal oxime
  参考文献：
  名称：

  Synthesis of methionine- and norleucine-derived phosphinopeptides

  摘要：

  We present herein a straightforward synthesis of N-Fmoc-protected synthons derived from a phosphinic analogue of methionine. These precursors were used Successfully for the solid-phase synthesis of methionine-mimic phosphinopeptides using BOP-catalyzed coupling without protection of the phosphoryl moiety. We also prepared a new type of pseudopeptide derived from a phosphinic analogue of norleucine with a -PO(OH)-CH(2)-COOR moiety. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.062

文献信息

• Copper-Catalyzed β-Lactam Formation Initiated by 1,3-Azaprotio Transfer of Oximes and Methyl Propiolate
  作者：Zhenjie Qi、Shaozhong Wang

  DOI：10.1021/acs.orglett.1c01937

  日期：2021.8.6

  A copper(II)-catalyzed protocol to construct trans-configured β-lactams and spirocyclic β-lactams from oximes and methyl propiolate has been developed, which features excellent substrate flexibility and diastereoselectivity (up to >99:1 dr). In situ FT-IR mechanistic experiments support that ketene species might be involved in the formation of β-lactams.

  已经开发了一种铜 (II) 催化的协议，用于从肟和丙炔酸甲酯构建反式配置的β-内酰胺和螺环 β-内酰胺，其具有出色的底物灵活性和非对映选择性（高达 >99:1 dr）。原位 FT-IR 机械实验支持乙烯酮物质可能参与 β-内酰胺的形成。
• Synthesis of phosphinic analogs of sulfur-containing amino acids
  作者：Yu. N. Zhukov、A. R. Khomutov、T. I. Osipova、R. M. Khomutov

  DOI：10.1007/bf02495302

  日期：1999.7

  Phosphinic analogs of the key compounds of the metabolism of methionine were synthesized. The compounds obtained were selectively oxidized either at the phosphinic group or at the sulfur-containing fragment.

  合成了蛋氨酸代谢的关键化合物的膦类似物。所得化合物在次膦基或含硫片段处被选择性氧化。
• Synthesis of methionine- and norleucine-derived phosphinopeptides
  作者：Radek Liboska、Jan Pícha、Ivona Hančlová、Miloš Buděšínský、Miloslav Šanda、Jiří Jiráček

  DOI：10.1016/j.tetlet.2008.07.062

  日期：2008.9

  We present herein a straightforward synthesis of N-Fmoc-protected synthons derived from a phosphinic analogue of methionine. These precursors were used Successfully for the solid-phase synthesis of methionine-mimic phosphinopeptides using BOP-catalyzed coupling without protection of the phosphoryl moiety. We also prepared a new type of pseudopeptide derived from a phosphinic analogue of norleucine with a -PO(OH)-CH(2)-COOR moiety. (C) 2008 Elsevier Ltd. All rights reserved.