tert-butylN-(1-benzofuran-3-yl)carbamate | 1935192-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: tert-butylN-(1-benzofuran-3-yl)carbamate
• 英文别名: tert-butyl N-(1-benzofuran-3-yl)carbamate
• CAS: 1935192-97-4
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.26
• InChiKey: TYUPVMGBIXSHEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butylN-(1-benzofuran-3-yl)carbamate 、 mesityl (E)-2-diazo-4-(3,4,5-trimethoxyphenyl)but-3-enoate 在 C₄₈H₂₈Cl₂F₂₄Rh₂ 作用下， 以 1,2-二氯乙烷 为溶剂， 以89 %的产率得到mesityl(R,E)-4-(3-((tert-butoxycarbonyl)amino)benzofuran-2-yl)-4-(3,4,5-trimethoxyphenyl)but-2-enoate
  参考文献：
  名称：

  Rhodium(I) Carbene‐Promoted Enantioselective C−H Functionalization of Simple Unprotected Indoles, Pyrroles and Heteroanalogues: New Mechanistic Insights

  摘要：

  A rhodium(I)‐diene catalyzed highly enantioselective C(sp2)−H functionalization of simple unprotected indoles, pyrroles, and their common analogues such as furans, thiophenes, and benzofurans with arylvinyldiazoesters has been developed for the first time. This transformation features unusual site‐selectivity exclusively at the vinyl terminus of arylvinylcarbene and enables a reliable and rapid synthetic protocol to access a distinctive class of diarylmethine‐bearing α,β‐unsaturated esters containing a one or two heteroarene‐attached tertiary carbon stereocenter in high yields and excellent enantioselectivities under mild reaction conditions. Mechanistic studies and DFT calculations suggest that, compared to the aniline substrate, the more electron‐rich indole substrate lowers the C−C addition barrier and alters the rate‐determining step to the reductive elimination, leading to different isotope effect.

  DOI：

  10.1002/anie.202207008