N-((1S,2S,6R,8S)-2,9,9-Trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-ylmethyl)-acetamide

• 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: N-((1S,2S,6R,8S)-2,9,9-Trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-ylmethyl)-acetamide
• 英文别名: N-[[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]methyl]acetamide
• 化学式: C₁₃H₂₂BNO₃
• 分子量: 251.134
• InChiKey: BHSVTJQFJJBVGQ-KQXIARHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-((1S,2S,6R,8S)-2,9,9-Trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-ylmethyl)-acetamide 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 acetamidomethylboronic acid
  参考文献：
  名称：

  Synthesis and Structural Investigation of Internally Coordinated α-Amidoboronic Acids

  摘要：

  Six new N-acyl-boroGly derivatives, along with their N-acyl-boroSar analogues, have been synthesized by modification of conventional procedures. Structural characterization of these alpha-amidoboronic acids was accomplished by extensive use of B-11 and H-1 NMR spectroscopy. These compounds were prepared to determine the extent of intramolecular B-O dative bond formation within the context of a five-membered (:O=C-N-C-B) ring motif. It is shown that the formation of such dative bonds depends on the nature of the substituents at both the acyl carbon and the nitrogen atoms. Computational evidence from second-order Moller-Plesset perturbation theory is provided in support of these findings.

  DOI：

  10.1021/jo051757h
• 作为产物：
  描述：

  (3AS,4S,6S,7AR)-六氢-3A,5,5-三甲基-4,6-甲桥-1,3,2-苯并二氧硼烷-2-甲胺盐酸盐 、 乙酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-((1S,2S,6R,8S)-2,9,9-Trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-ylmethyl)-acetamide
  参考文献：
  名称：

  Synthesis and Structural Investigation of Internally Coordinated α-Amidoboronic Acids

  摘要：

  Six new N-acyl-boroGly derivatives, along with their N-acyl-boroSar analogues, have been synthesized by modification of conventional procedures. Structural characterization of these alpha-amidoboronic acids was accomplished by extensive use of B-11 and H-1 NMR spectroscopy. These compounds were prepared to determine the extent of intramolecular B-O dative bond formation within the context of a five-membered (:O=C-N-C-B) ring motif. It is shown that the formation of such dative bonds depends on the nature of the substituents at both the acyl carbon and the nitrogen atoms. Computational evidence from second-order Moller-Plesset perturbation theory is provided in support of these findings.

  DOI：

  10.1021/jo051757h