(+)-4-hydroxy-1,4-diphenylbutan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-4-hydroxy-1,4-diphenylbutan-1-one
• 英文别名: (4R)-4-hydroxy-1,4-diphenylbutan-1-one
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: BQSKJEGGHVHTRT-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-联苯甲酰乙烷 在 硼烷四氢呋喃络合物 、 Cp* Ir[(S,S)-Msdpen] 作用下， 以 四氢呋喃 为溶剂， 20.0~30.0 ℃ 、101.33 kPa 条件下， 反应 64.0h， 生成 (+)-4-hydroxy-1,4-diphenylbutan-1-one
  参考文献：
  名称：

  Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands

  摘要：

  Asymmetric aerobic oxidation of a range of meso- and prochiral diols with chiral bifunctional Ir catalysts is described. A high level of chiral discrimination ability of Cp*Ir complexes derived from (S,S)-1,2-diphenylethylenediamine was successfully demonstrated by desymmetrization of secondary benzylic diols such as cis-indan-1,3-diol and cis-1,4-diphenylbutane-1,4-diol, providing the corresponding (R)-hydroxyl ketones with excellent chemo- and enantioselectivities. Enantiotopic group discrimination in oxidation of symmetrical primary 1,4- and 1,5-diols gave rise to chiral lactones with moderate ees under similar aerobic conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.103

文献信息

• Asymmetric Ring-Opening of Cyclopropyl Ketones with Thiol, Alcohol, and Carboxylic Acid Nucleophiles Catalyzed by a Chiral<i>N</i>,<i>N</i>′-Dioxide-Scandium(III) Complex
  作者：Yong Xia、Lili Lin、Fenzhen Chang、Xuan Fu、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/anie.201506909

  日期：2015.11.9

  efficient asymmetric ring‐opening reaction of cyclopropyl ketones with a broad range of thiols, alcohols and carboxylic acids has been first realized by using a chiral N,N′‐dioxide–scandium(III) complex as catalyst. The corresponding sulfides, ethers, and esters were obtained in up to 99 % yield and 95 % ee. This is also the first example of one catalytic system working for the ring‐opening reaction of donor–acceptor

  通过使用手性N，N'-二氧化物-scan（III）络合物作为催化剂，首次实现了环丙基酮与各种硫醇，醇和羧酸的高效不对称开环反应。以高达99％的收率和95％的ee获得相应的硫化物，醚和酯。这也是一个催化体系用于供体-受体环丙烷与三种不同亲核试剂开环反应的第一个例子，更不用说不对称形式了。
• Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands
  作者：Junki Moritani、Yasuharu Hasegawa、Yoshihito Kayaki、Takao Ikariya

  DOI：10.1016/j.tetlet.2013.12.103

  日期：2014.2

  Asymmetric aerobic oxidation of a range of meso- and prochiral diols with chiral bifunctional Ir catalysts is described. A high level of chiral discrimination ability of Cp*Ir complexes derived from (S,S)-1,2-diphenylethylenediamine was successfully demonstrated by desymmetrization of secondary benzylic diols such as cis-indan-1,3-diol and cis-1,4-diphenylbutane-1,4-diol, providing the corresponding (R)-hydroxyl ketones with excellent chemo- and enantioselectivities. Enantiotopic group discrimination in oxidation of symmetrical primary 1,4- and 1,5-diols gave rise to chiral lactones with moderate ees under similar aerobic conditions. (C) 2014 Elsevier Ltd. All rights reserved.