2-hydroxymethyl-1-((1S,4R)-10-camphorsulfonyl)pyrrole | 251947-73-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-hydroxymethyl-1-((1S,4R)-10-camphorsulfonyl)pyrrole
• 英文别名: (1S,4R)-1-[[2-(hydroxymethyl)pyrrol-1-yl]sulfonylmethyl]-7,7-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 251947-73-6
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: QVVCLEHUNSHIBY-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-1-((1S,4R)-10-camphorsulfonyl)pyrrole 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 生成 2-chloromethyl-1-((1S,4R)-10-camphorsulfonyl)pyrrole
  参考文献：
  名称：

  Properties and Reactions of Ring-Deactivated Deuterated Hydroxymethylpyrroles

  摘要：

  [GRAPHICS]Chlorination and mesylation at the hydroxymethyl position of deuterium-labeled N-substituted 2-(hydroxymethyl)pyrroles has been shown to occur with some involvement of a highly reactive azafulvenium species. An electron-withdrawing camphorsulfonyl substituent on nitrogen provides a chiral handle for direct analysis of the stereochemical outcome of the reactions by H-1 NMR.

  DOI：

  10.1021/ol990959v
• 作为产物：
  描述：

  1-((1S,4R)-10-camphorsulfonyl)pyrrole-2-carboxaldehyde 在 zinc borohydride 作用下， 以 乙醚 为溶剂， 以88%的产率得到2-hydroxymethyl-1-((1S,4R)-10-camphorsulfonyl)pyrrole
  参考文献：
  名称：

  Properties and Reactions of Ring-Deactivated Deuterated Hydroxymethylpyrroles

  摘要：

  [GRAPHICS]Chlorination and mesylation at the hydroxymethyl position of deuterium-labeled N-substituted 2-(hydroxymethyl)pyrroles has been shown to occur with some involvement of a highly reactive azafulvenium species. An electron-withdrawing camphorsulfonyl substituent on nitrogen provides a chiral handle for direct analysis of the stereochemical outcome of the reactions by H-1 NMR.

  DOI：

  10.1021/ol990959v

文献信息

• Properties and Reactions of Ring-Deactivated Deuterated Hydroxymethylpyrroles
  作者：Andrew D. Abell、Brent K. Nabbs

  DOI：10.1021/ol990959v

  日期：1999.11.1

  [GRAPHICS]Chlorination and mesylation at the hydroxymethyl position of deuterium-labeled N-substituted 2-(hydroxymethyl)pyrroles has been shown to occur with some involvement of a highly reactive azafulvenium species. An electron-withdrawing camphorsulfonyl substituent on nitrogen provides a chiral handle for direct analysis of the stereochemical outcome of the reactions by H-1 NMR.