3-[3-(4-boronophenyl)propyl]cyclobutanone ethylene ketal | 254893-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[3-(4-boronophenyl)propyl]cyclobutanone ethylene ketal
• 英文别名: [4-[3-(5,8-Dioxaspiro[3.4]octan-2-yl)propyl]phenyl]boronic acid
• CAS: 254893-01-1
• 化学式: C₁₅H₂₁BO₄
• 分子量: 276.14
• InChiKey: CKFRBXVEBIQODH-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  453.7±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[3-(4-boronophenyl)propyl]cyclobutanone ethylene ketal 在 盐酸 作用下， 以 甲醇 为溶剂， 以83%的产率得到3-[3-(4-boronophenyl)propyl]cyclobutanone
  参考文献：
  名称：

  4-Dihydroxyborylphenyl Analogues of 1-Aminocyclobutanecarboxylic Acids:  Potential Boron Neutron Capture Therapy Agents

  摘要：

  A series of 4-dihydroxyborylphenyl analogues of an unnatural alpha-amino acid, 1-aminocyclobutanecarboxylic acid (ACBC), was synthesized. Varying numbers of methylene units were introduced between the 4-boronophenyl and ACBC moieties in order to introduce different degrees of lipophilicity into the molecules. The key step in the syntheses was the preparation of the precursor p-boronophenyl-substituted cyclobutanones which were subsequently converted to the desired amino acids via the Bucherer-Strecker reaction.

  DOI：

  10.1021/jo990878c
• 作为产物：
  描述：

  3-[3-(4-bromophenyl)propyl]cyclobutanone 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 21.0h， 生成 3-[3-(4-boronophenyl)propyl]cyclobutanone ethylene ketal
  参考文献：
  名称：

  4-Dihydroxyborylphenyl Analogues of 1-Aminocyclobutanecarboxylic Acids:  Potential Boron Neutron Capture Therapy Agents

  摘要：

  A series of 4-dihydroxyborylphenyl analogues of an unnatural alpha-amino acid, 1-aminocyclobutanecarboxylic acid (ACBC), was synthesized. Varying numbers of methylene units were introduced between the 4-boronophenyl and ACBC moieties in order to introduce different degrees of lipophilicity into the molecules. The key step in the syntheses was the preparation of the precursor p-boronophenyl-substituted cyclobutanones which were subsequently converted to the desired amino acids via the Bucherer-Strecker reaction.

  DOI：

  10.1021/jo990878c

文献信息

• 4-Dihydroxyborylphenyl Analogues of 1-Aminocyclobutanecarboxylic Acids:  Potential Boron Neutron Capture Therapy Agents
  作者：Rajiv R. Srivastava、Robert R. Singhaus、George W. Kabalka

  DOI：10.1021/jo990878c

  日期：1999.11.1

  A series of 4-dihydroxyborylphenyl analogues of an unnatural alpha-amino acid, 1-aminocyclobutanecarboxylic acid (ACBC), was synthesized. Varying numbers of methylene units were introduced between the 4-boronophenyl and ACBC moieties in order to introduce different degrees of lipophilicity into the molecules. The key step in the syntheses was the preparation of the precursor p-boronophenyl-substituted cyclobutanones which were subsequently converted to the desired amino acids via the Bucherer-Strecker reaction.