[1,2,5]dithiazocan-6-one | 200435-30-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: [1,2,5]dithiazocan-6-one
• 英文别名: 1,2,5-Dithiazocan-6-on；1,2,5-dithiazocan-6-one
• CAS: 200435-30-9
• 化学式: C₅H₉NOS₂
• 分子量: 163.265
• InChiKey: FHHSBYNOZRMMOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1,2,5]dithiazocan-6-one 在 氘氧化钠 、 1,4-丁二硫醇 作用下， 以 氘代二甲亚砜 、 water-d2 为溶剂， 生成 3-mercapto-N-(2-mercapto-ethyl)-propionamide
  参考文献：
  名称：

  Synthesis, redox properties, and conformational analysis of vicinal disulfide ring mimics

  摘要：

  A vicinal disulfide ring (VDR) results from disulfide-bond formation between two adjacent cysteine residues. This eight-membered ring is a rare motif in protein structures and is functionally important to those few proteins that posses it. This article focuses on the construction of strained and unstrained VDR mimics, discernment of the preferred conformation of these mimics, and the determination of their respective disulfide redox potentials. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.085
• 作为产物：
  描述：

  3-mercapto-N-(2-mercapto-ethyl)-propionamide 在 air 、 Celite 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 120.0h， 以18%的产率得到[1,2,5]dithiazocan-6-one
  参考文献：
  名称：

  Synthesis, redox properties, and conformational analysis of vicinal disulfide ring mimics

  摘要：

  A vicinal disulfide ring (VDR) results from disulfide-bond formation between two adjacent cysteine residues. This eight-membered ring is a rare motif in protein structures and is functionally important to those few proteins that posses it. This article focuses on the construction of strained and unstrained VDR mimics, discernment of the preferred conformation of these mimics, and the determination of their respective disulfide redox potentials. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.085

文献信息

• 1,2-dithia-5-azacyclooctan-6-one and related compounds: Synthesis and conformation
  作者：Susana Caveda Cepas、Michael North

  DOI：10.1016/s0040-4020(97)10087-4

  日期：1997.12

  n-6-one 11, the parent member of a heterocyclic ring synthesis is reported. Compound 11 was found by nOe experiments to exist in a conformation with a trans-amide bond. The substituted derivatives 12 and 13 were also prepared and compound 12 was found to possess a trans-amide bond whilst for compound 13 three conformations were identified with the major conformer possessing a cis-amide bond.

  1,2-二硫杂-5- azacyclooctan -6-酮的第一合成11报告，杂环合成的父构件。通过nOe实验发现化合物11以具有反酰胺键的构象存在。还制备了取代的衍生物12和13，发现化合物12具有反酰胺键，而对于化合物13，三个构象被鉴定为具有顺式-酰胺键的主要构象剂。