Dimethyl D-(3R)-N-(9-phenylfluoren-9-yl)-N-benzyl-3-allylaspartate

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Dimethyl D-(3R)-N-(9-phenylfluoren-9-yl)-N-benzyl-3-allylaspartate
• 英文别名: dimethyl (2R,3R)-2-[benzyl-(9-phenylfluoren-9-yl)amino]-3-prop-2-enylbutanedioate
• 化学式: C₃₅H₃₃NO₄
• 分子量: 531.651
• InChiKey: BQIUVBQKVZCAFO-QLWXXVCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dimethyl D-(3R)-N-(9-phenylfluoren-9-yl)-N-benzyl-3-allylaspartate 在 二甲基硫 、 臭氧 作用下， 生成 (3R,4R)-N-(9-Phenylfluoren-9-yl)-N-benzyl-4-amino-3,4-dicarbomethoxybutanal
  参考文献：
  名称：

  2,3-Pyrrolidinedicarboxylates as Neurotransmitter Conformer Mimics: Enantioselective Synthesis via Chelation-Controlled Enolate Alkylation

  摘要：

  Conformationally restricted analogs of naturally-occurring amino acids can serve in a variety of ways as protein structure/function probes. A diastereo- and enantioselective synthesis of the four stereoisomers of 2,3-pyrrolidinedicarboxylic acid (an analog of aspartic acid) are described in this paper. The key step is a Rapoport-type aspartate alkylation that can be controlled to give good yields of either diastereomer as a function of enolate geometry. A novel type of chelation control is proposed to account for these results.

  DOI：

  10.1021/jo00088a030
• 作为产物：
  描述：

  9-溴-9-苯基芴 在 potassium phosphate 、 lead(II) nitrate 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 25.08h， 生成 Dimethyl D-(3R)-N-(9-phenylfluoren-9-yl)-N-benzyl-3-allylaspartate
  参考文献：
  名称：

  2,3-Pyrrolidinedicarboxylates as Neurotransmitter Conformer Mimics: Enantioselective Synthesis via Chelation-Controlled Enolate Alkylation

  摘要：

  Conformationally restricted analogs of naturally-occurring amino acids can serve in a variety of ways as protein structure/function probes. A diastereo- and enantioselective synthesis of the four stereoisomers of 2,3-pyrrolidinedicarboxylic acid (an analog of aspartic acid) are described in this paper. The key step is a Rapoport-type aspartate alkylation that can be controlled to give good yields of either diastereomer as a function of enolate geometry. A novel type of chelation control is proposed to account for these results.

  DOI：

  10.1021/jo00088a030

文献信息

• 2,3-Pyrrolidinedicarboxylates as Neurotransmitter Conformer Mimics: Enantioselective Synthesis via Chelation-Controlled Enolate Alkylation
  作者：John M. Humphrey、Richard J. Bridges、Jill A. Hart、A. Richard Chamberlin

  DOI：10.1021/jo00088a030

  日期：1994.5

  Conformationally restricted analogs of naturally-occurring amino acids can serve in a variety of ways as protein structure/function probes. A diastereo- and enantioselective synthesis of the four stereoisomers of 2,3-pyrrolidinedicarboxylic acid (an analog of aspartic acid) are described in this paper. The key step is a Rapoport-type aspartate alkylation that can be controlled to give good yields of either diastereomer as a function of enolate geometry. A novel type of chelation control is proposed to account for these results.