3-[2-(4-boronophenyl)ethyl]cyclobutanone ethylene ketal | 254893-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-(4-boronophenyl)ethyl]cyclobutanone ethylene ketal
• 英文别名: (4-(2-(5,8-Dioxaspiro[3.4]octan-2-yl)ethyl)phenyl)boronic acid；[4-[2-(5,8-dioxaspiro[3.4]octan-2-yl)ethyl]phenyl]boronic acid
• CAS: 254893-00-0
• 化学式: C₁₄H₁₉BO₄
• 分子量: 262.113
• InChiKey: PTAJYDMVMGUONA-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  443.8±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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-[2-(4-boronophenyl)ethyl]cyclobutanone ethylene ketal 在 盐酸 作用下， 以 甲醇 为溶剂， 以78%的产率得到3-[2-(4-boronophenyl)ethyl]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：

  4-(3-丁烯-1-基)溴苯 在 正丁基锂 、 铜 、 对甲苯磺酸 、 溶剂黄146 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 苯 为溶剂， 反应 27.5h， 生成 3-[2-(4-boronophenyl)ethyl]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.