dimethyl-N^α-(9-phenylfluoren-9-yl)-3,3-dimethyl-D-aspartate | 230973-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: dimethyl-N^α-(9-phenylfluoren-9-yl)-3,3-dimethyl-D-aspartate
• 英文别名: dimethyl (3R)-2,2-dimethyl-3-[(9-phenylfluoren-9-yl)amino]butanedioate
• CAS: 230973-45-2
• 化学式: C₂₇H₂₇NO₄
• 分子量: 429.516
• InChiKey: FKVAHAWUZKRMOJ-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl-N^α-(9-phenylfluoren-9-yl)-3,3-dimethyl-D-aspartate 在 palladium on activated charcoal 甲醇 、 sodium hydroxide 、 TEA 、 二苯基磷酸 、 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 magnesium 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 79.25h， 生成 N^α-tert-butyloxycarbonyl-N^δ-benzyloxycarbonyl-3,3-dimethyl-D-ornithine-methyl ester
  参考文献：
  名称：

  Synthesis of β,β-Dimethylated Amino Acid Building Blocks Utilizing the 9-Phenylfluorenyl Protecting Group

  摘要：

  Optically pure beta,beta-dimethylated amino acid building blocks with functionalized side chains have been prepared from D-aspartic acid. The dimethylation was accomplished by regioselective dialkylation of 9-phenylfluorenyl (PhFl)-protected aspartate diesters. The bulk of the PhFl protecting group also allowed for a variety of functional group manipulations to be carried out on the side chain without, affecting the C-alpha ester of the aspartate. As a result, the derivatives of the following novel amino acids were synthesized in this study: beta,beta-dimethyl-D-aspartic acid, beta,beta-dimethyl-D-homoserine, 3,3-dimethyl-D-2,4-diaminobutyric acid, beta,beta-dimethyl-D-lysine, beta,beta-dimethyl-D-homoglutamate, beta,beta-dimethyl-D-ornithine, and 3,3-dimethylazetidine-2-carboxylic acid. The beta,beta-dimethylated amino acids were synthesized in high enantiomeric excess as determined by coupling the, novel building blocks to chiral reagents.

  DOI：

  10.1021/jo982474a
• 作为产物：
  描述：

  (R)-2-(9-Phenyl-9H-fluoren-9-ylamino)-succinic acid dimethyl ester 、 碘甲烷 在 双(三甲基硅烷基)氨基钾 作用下， 生成 dimethyl-N^α-(9-phenylfluoren-9-yl)-3,3-dimethyl-D-aspartate
  参考文献：
  名称：

  Synthesis of β,β-Dimethylated Amino Acid Building Blocks Utilizing the 9-Phenylfluorenyl Protecting Group

  摘要：

  Optically pure beta,beta-dimethylated amino acid building blocks with functionalized side chains have been prepared from D-aspartic acid. The dimethylation was accomplished by regioselective dialkylation of 9-phenylfluorenyl (PhFl)-protected aspartate diesters. The bulk of the PhFl protecting group also allowed for a variety of functional group manipulations to be carried out on the side chain without, affecting the C-alpha ester of the aspartate. As a result, the derivatives of the following novel amino acids were synthesized in this study: beta,beta-dimethyl-D-aspartic acid, beta,beta-dimethyl-D-homoserine, 3,3-dimethyl-D-2,4-diaminobutyric acid, beta,beta-dimethyl-D-lysine, beta,beta-dimethyl-D-homoglutamate, beta,beta-dimethyl-D-ornithine, and 3,3-dimethylazetidine-2-carboxylic acid. The beta,beta-dimethylated amino acids were synthesized in high enantiomeric excess as determined by coupling the, novel building blocks to chiral reagents.

  DOI：

  10.1021/jo982474a