(2S,3S)-3-[(1,3-dioxoisoindolin-2-yl)sulfanyl]-1-phenylpent-4-en-2-yl carbamic acid tert-butyl ester | 1329427-83-9

• 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: (2S,3S)-3-[(1,3-dioxoisoindolin-2-yl)sulfanyl]-1-phenylpent-4-en-2-yl carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S,3S)-3-(1,3-dioxoisoindol-2-yl)sulfanyl-1-phenylpent-4-en-2-yl]carbamate
• CAS: 1329427-83-9
• 化学式: C₂₄H₂₆N₂O₄S
• 分子量: 438.547
• InChiKey: UBJTTZXVHLMFGP-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-噻吩基锂 、 (2S,3S)-3-[(1,3-dioxoisoindolin-2-yl)sulfanyl]-1-phenylpent-4-en-2-yl carbamic acid tert-butyl ester 以 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到(2S,3S)-tert-butyl 1-phenyl-3-(thiophen-2-ylthio)pent-4-en-2-ylcarbamate
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes

  摘要：

  An efficient synthesis of various protected syn-beta-sulfenyl amides is described. These are prepared from the corresponding enantiopure amino allylsilanes which are in turn obtained from naturally occurring amino acids. The key step for introduction of the sulfur substituent is a diastereoselective electrophilic sulfodesilylation which is carried out with phthalimidesulfenyl chloride. The resulting homochiral beta-phthalimidesulfenyl amines with an allylic sulforated stereogenic center are useful building blocks, as they represent a starting point for subsequent functional manipulations.

  DOI：

  10.1021/jo2010878
• 作为产物：
  描述：

  4-<<(tert-butyloxy)carbonyl>amino>-3-hydroxy-5-phenyl-1-pentene 在 4-二甲氨基吡啶 、 甲基锂 、 copper(l) cyanide 、 三乙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3S)-3-[(1,3-dioxoisoindolin-2-yl)sulfanyl]-1-phenylpent-4-en-2-yl carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes

  摘要：

  An efficient synthesis of various protected syn-beta-sulfenyl amides is described. These are prepared from the corresponding enantiopure amino allylsilanes which are in turn obtained from naturally occurring amino acids. The key step for introduction of the sulfur substituent is a diastereoselective electrophilic sulfodesilylation which is carried out with phthalimidesulfenyl chloride. The resulting homochiral beta-phthalimidesulfenyl amines with an allylic sulforated stereogenic center are useful building blocks, as they represent a starting point for subsequent functional manipulations.

  DOI：

  10.1021/jo2010878