dithiocarbonic acid S-[1,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentyl] ester O-ethyl ester | 1180130-22-6

• 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: dithiocarbonic acid S-[1,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentyl] ester O-ethyl ester
• 英文别名: O-ethyl 1,5-bis(1,3-dioxoisoindol-2-yl)pentylsulfanylmethanethioate
• CAS: 1180130-22-6
• 化学式: C₂₄H₂₂N₂O₅S₂
• 分子量: 482.581
• InChiKey: WYCPFRCFDQUVLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dithiocarbonic acid S-[1,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentyl] ester O-ethyl ester 、 烯丙基腈 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Functional Primary Amines and Diamines from α-Aminoacids. A Concise Route to Substituted 2-Aminotetralins

  摘要：

  S-Phthalimidomethyl xanthates derived from various alpha-amino acids add efficiently to a range of unactivated alkenes to give a variety of highly functionalized, protected amines. In the case of phenylalanine and tyrosine derived xanthates, the adducts can be further converted into the rare 4-substituted 2-aminotetralines by a radical ring closure onto the aromatic ring.

  DOI：

  10.1021/ol901263t
• 作为产物：
  描述：

  C₂₅H₂₂N₂O₆S₂ 以 乙酸乙酯 为溶剂， 反应 1.0h， 以2.6 g的产率得到dithiocarbonic acid S-[1,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentyl] ester O-ethyl ester
  参考文献：
  名称：

  Functional Primary Amines and Diamines from α-Aminoacids. A Concise Route to Substituted 2-Aminotetralins

  摘要：

  S-Phthalimidomethyl xanthates derived from various alpha-amino acids add efficiently to a range of unactivated alkenes to give a variety of highly functionalized, protected amines. In the case of phenylalanine and tyrosine derived xanthates, the adducts can be further converted into the rare 4-substituted 2-aminotetralines by a radical ring closure onto the aromatic ring.

  DOI：

  10.1021/ol901263t

文献信息

• A convergent route to structures with multiple contiguous carbon–nitrogen bonds. The divergent role of N-acyl groups
  作者：Songzhe Han、Samir Z. Zard

  DOI：10.1016/j.tet.2016.05.085

  日期：2016.12

  to N,N-diacetyl imidazol-2-one can be followed by a second addition to N,N-di-Boc imidazol-2-one to give after reductive dexanthylation a protected tetra-amine possessing four contiguous carbon–nitrogen bonds, or even five if the starting xanthate itself bears a protected amine. The success of this sequence hinges on the difference in radical stability between radicals substituted by an N-acyl and

  将黄原酸酯自由基加成到N，N-二乙酰基咪唑-2-酮上，然后第二加成N，N-二-乙酰基咪唑-2-酮，在还原性右胸腺嘧啶化后得到具有四个连续碳的受保护的四胺。 -氮键，或者如果起始黄药本身带有受保护的胺，则为五个。该序列的成功取决于被N-酰基和N-氨基甲酰基氮取代的基团之间的基团稳定性的差异，这可以控制基团的添加并防止低聚物的形成。
• Functional Primary Amines and Diamines from α-Aminoacids. A Concise Route to Substituted 2-Aminotetralins
  作者：Béatrice Quiclet-Sire、Guillaume Revol、Samir Z. Zard

  DOI：10.1021/ol901263t

  日期：2009.8.20

  S-Phthalimidomethyl xanthates derived from various alpha-amino acids add efficiently to a range of unactivated alkenes to give a variety of highly functionalized, protected amines. In the case of phenylalanine and tyrosine derived xanthates, the adducts can be further converted into the rare 4-substituted 2-aminotetralines by a radical ring closure onto the aromatic ring.