2-oxobenzo[d][1,3]oxathiole-4-carbaldehyde | 901126-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-oxobenzo[d][1,3]oxathiole-4-carbaldehyde
• 英文别名: 2-Oxo-1,3-benzoxathiole-4-carbaldehyde；2-oxo-1,3-benzoxathiole-4-carbaldehyde
• CAS: 901126-77-0
• 化学式: C₈H₄O₃S
• 分子量: 180.184
• InChiKey: NUDWFESHYIMSTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-oxobenzo[d][1,3]oxathiole-4-carbaldehyde 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-hydroxy-2-mercaptobenzaldehyde
  参考文献：
  名称：

  Studies Related to the Relative Thermodynamic Stability of C-Terminal Peptidyl Esters of O-Hydroxy Thiophenol:  Emergence of a Doable Strategy for Non-Cysteine Ligation Applicable to the Chemical Synthesis of Glycopeptides

  摘要：

  A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.

  DOI：

  10.1021/ja061588y
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 在 氢氧化钾 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 三甘醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.42h， 生成 2-oxobenzo[d][1,3]oxathiole-4-carbaldehyde
  参考文献：
  名称：

  Studies Related to the Relative Thermodynamic Stability of C-Terminal Peptidyl Esters of O-Hydroxy Thiophenol:  Emergence of a Doable Strategy for Non-Cysteine Ligation Applicable to the Chemical Synthesis of Glycopeptides

  摘要：

  A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.

  DOI：

  10.1021/ja061588y

文献信息

• Studies Related to the Relative Thermodynamic Stability of C-Terminal Peptidyl Esters of O-Hydroxy Thiophenol:  Emergence of a Doable Strategy for Non-Cysteine Ligation Applicable to the Chemical Synthesis of Glycopeptides
  作者：Gong Chen、J. David Warren、Jiehao Chen、Bin Wu、Qian Wan、Samuel J. Danishefsky

  DOI：10.1021/ja061588y

  日期：2006.6.1

  A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.