3-phenyl-1-(3-acetoxyphenyl)propan-1-one | 152754-61-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-phenyl-1-(3-acetoxyphenyl)propan-1-one
• 英文别名: 3-(3-Phenylpropanoyl)phenyl acetate；[3-(3-phenylpropanoyl)phenyl] acetate
• CAS: 152754-61-5
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: GOVDLUUIGXNKAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(3-acetoxyphenyl)propan-1-one 在 (+)-二异松蒎基氯硼烷 作用下， 生成 (1R)-3-phenyl-1-(3-acetoxyphenyl)propan-1-ol
  参考文献：
  名称：

  二级有机三氟硼酸盐的立体有择交叉偶联：1-（苄氧基）烷基三氟硼酸钾

  摘要：

  1-(烷氧基/酰氧基)烷基三氟硼酸钾是通过铜催化的醛二硼化反应和随后得到的1-(羟基)烷基三氟硼酸钾的转化合成的。钯催化的 Suzuki-Miyaura 反应使用 1-（苄氧基）烷基三氟硼酸钾与芳基和杂芳基氯化物，以高产率获得受保护的仲醇。通过使用苄基保护基团避免了 β-氢化物消除途径，建议通过芳烃与金属中心的配位来稳定二有机钯中间体。这种交叉偶联是立体有择的，完全保留了立体化学。

  DOI：

  10.1021/ja307861n
• 作为产物：
  描述：

  magnesium,ethylbenzene,bromide 在 吡啶 、 chromium(VI) oxide 、 硫酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.0h， 生成 3-phenyl-1-(3-acetoxyphenyl)propan-1-one
  参考文献：
  名称：

  Design, synthesis, and kinetic evaluation of high-affinity FKBP ligands and the X-ray crystal structures of their complexes with FKBP12

  摘要：

  The design and synthesis of high-affinity FKBP12 ligands is described. These compounds potently inhibit the cis-trans-peptidylprolyl isomerase (rotamase) activity catalyzed by FKBP12 with inhibition constants (K(i,app)) as low as 1 nM, yet they possess remarkable structural simplicity relative to FK506 and rapamycin, from which they are conceptually derived. The atomic structures of three FKBP12-ligand complexes and of one unbound ligand were determined by X-ray crystallography and are compared to the FKBP12-FK506 and FKBP12-rapamycin complexes.

  DOI：

  10.1021/ja00075a008

文献信息

• US6316405B1
  申请人：——

  公开号：US6316405B1

  公开（公告）日：2001-11-13
• Design, synthesis, and kinetic evaluation of high-affinity FKBP ligands and the X-ray crystal structures of their complexes with FKBP12
  作者：Dennis A. Holt、Juan I. Luengo、Dennis S. Yamashita、Hye Ja Oh、Arda L. Konialian、Hwa Kwo Yen、Leonard W. Rozamus、Martin Brandt、Mary J. Bossard、Mark A. Levy、Drake S. Eggleston、Jun Liang、L. Wayne Schultz、Thomas J. Stout、Jon Clardy

  DOI：10.1021/ja00075a008

  日期：1993.11.1

  The design and synthesis of high-affinity FKBP12 ligands is described. These compounds potently inhibit the cis-trans-peptidylprolyl isomerase (rotamase) activity catalyzed by FKBP12 with inhibition constants (K(i,app)) as low as 1 nM, yet they possess remarkable structural simplicity relative to FK506 and rapamycin, from which they are conceptually derived. The atomic structures of three FKBP12-ligand complexes and of one unbound ligand were determined by X-ray crystallography and are compared to the FKBP12-FK506 and FKBP12-rapamycin complexes.
• Stereospecific Cross-Coupling of Secondary Organotrifluoroborates: Potassium 1-(Benzyloxy)alkyltrifluoroborates
  作者：Gary A. Molander、Steven R. Wisniewski

  DOI：10.1021/ja307861n

  日期：2012.10.10

  Potassium 1-(alkoxy/acyloxy)alkyltrifluoroborates have been synthesized through a copper-catalyzed diboration of aldehydes and subsequent conversion of the resulting potassium 1-(hydroxy)alkyltrifluoroborates. The palladium-catalyzed Suzuki-Miyaura reaction employing the potassium 1-(benzyloxy)alkyltrifluoroborates with aryl and heteroaryl chlorides provides access to protected secondary alcohols in

  1-(烷氧基/酰氧基)烷基三氟硼酸钾是通过铜催化的醛二硼化反应和随后得到的1-(羟基)烷基三氟硼酸钾的转化合成的。钯催化的 Suzuki-Miyaura 反应使用 1-（苄氧基）烷基三氟硼酸钾与芳基和杂芳基氯化物，以高产率获得受保护的仲醇。通过使用苄基保护基团避免了 β-氢化物消除途径，建议通过芳烃与金属中心的配位来稳定二有机钯中间体。这种交叉偶联是立体有择的，完全保留了立体化学。