N-((S)-3-diazo-1-methyl-2-oxo-propyl)-phthalimide | 67919-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-((S)-3-diazo-1-methyl-2-oxo-propyl)-phthalimide
• 英文别名: N-((S)-3-Diazo-1-methyl-2-oxo-propyl)-phthalimid；2-[(2S)-4-diazo-3-oxobutan-2-yl]isoindole-1,3-dione
• CAS: 67919-81-7
• 化学式: C₁₂H₉N₃O₃
• 分子量: 243.222
• InChiKey: SZOWTJZPCHLEFJ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-((S)-3-diazo-1-methyl-2-oxo-propyl)-phthalimide 在 氢溴酸 作用下， 以 乙醚 为溶剂， 反应 0.75h， 以85%的产率得到(S)-1-bromo-3-phthalimidobutan-2-one
  参考文献：
  名称：

  N-邻苯二甲酰基α-氨基酮的立体选择性还原：非外消旋苏-α-氨基环氧化物的快速合成

  摘要：

  衍生自对映体纯α-重氮酮Ñ -Pht氨基酸已经被转化为苏经由溴化氢处理，然后进行高度-α氨基环氧化物顺式与的LiAlH（OBu- -选择性还原吨）3。

  DOI：

  10.1016/s0957-4166(99)00177-9
• 作为产物：
  描述：

  邻苯二甲酰基-L-丙氨酸 在 氯化亚砜 作用下， 以 乙醚 、 苯 为溶剂， 生成 N-((S)-3-diazo-1-methyl-2-oxo-propyl)-phthalimide
  参考文献：
  名称：

  非对映选择性还原的Ñ -phthaloylα氨基酮：合成顺-3-氨基丙烷-1,2-二醇衍生物

  摘要：

  的LiAlH（OBu-吨）3还原手性池的衍生Ñ -phthaloylα氨基α'乙酰氧基酮导致的非对映选择性容易合成顺式-3-氨基-1,2-二醇（> 75％去）。

  DOI：

  10.1016/s0040-4039(00)01993-6

文献信息

• Homochiral group transfer in organic synthesis viaα-diazocarbonyl intermediates
  作者：Jeremiah C. Collins、Brid M. Dilworth、Norah T. Garvey、Michael Kennedy、M. Anthony McKervey、Michael B. O'Sullivan

  DOI：10.1039/c39900000362

  日期：——

  Optically active diazoketones derived from N-protected amino acids and (S)-2-chloropropionic acid have been used as homochiral group transfer reagents in the synthesis of various optically active α-functionalised ketones and related compounds.

  衍生自N-保护的氨基酸和（S）-2-氯丙酸的旋光重氮酮已经用作合成各种旋光α-官能化酮和相关化合物的手性基团转移试剂。
• Configurational studies in synthetic analgesics
  作者：A. H. Beckett、A. F. Casy

  DOI：10.1039/jr9550000900

  日期：——
• Cycloadditions of Ketenes Generated in the Wolff Rearrangement. Stereoselective Synthesis of Aminoalkyl-Substituted β-Lactams from α-Amino Acids
  作者：Joachim Podlech、Michael R. Linder

  DOI：10.1021/jo9705069

  日期：1997.8.1

  Diazo ketones 1-16, derived from suitable protected amino acids (Ala, Leu, Val, Ile, Tie, Phe, Pro, Orn, Lys, Ser, and Thr), have been photochemically rearranged, leading to the corresponding ketene intermediates. They were trapped with N-benzylbenzaldimine 17 to give beta-lactams S-SS in up to 90% yield. In these cycloadditions, two of the four possible diastereoisomers were formed exclusively. The selectivity ranged from 60:40 to 93:7 and the bulkiness of the parent amino acid side chain is the governing factor. The relative configuration was-proved by three X-ray crystal structures. The diastereoselectivity in these reactions is also influenced by the use of chiral N-phenethylbenzaldimines 34 and 35. With regard to a projected deprotection of the lactam-nitrogen, N-allyl- (49) and N-(p-methoxybenzyl)benzaldimine (44) were used in this reaction. This led to the N-allyl beta-lactams 50 and 51 in 62 and 56% yield, respectively, and to the p-methoxybenzyl-substituted beta-lactams 45 and 46 (50 and 72% yield). The p-methoxybenzyl, group on the valine-derived beta-lactam 45a can be cleaved with potassium peroxodisulfate in 63% yield.
• Synthesis of aminoalkylglyoxal derivatives. II. Aminoalkyglyoxal derivatives of _L-alanine, β-alanine, and _L-tyrosine
  作者：K. Balenovic´、D. Cerar、L. Filipovic´

  DOI：10.1021/jo50013a015

  日期：1953.7
• Fles; Markovac-Prpic, Croatica Chemica Acta, 1957, vol. 29, p. 79,81
  作者：Fles、Markovac-Prpic

  DOI：——

  日期：——