(2S,3R)-2-hydroxy-3-methyl-1,4-diphenylbutane-1,4-dione

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (2S,3R)-2-hydroxy-3-methyl-1,4-diphenylbutane-1,4-dione
• 英文别名: (2S,3S)-2-hydroxy-3-methyl-1,4-diphenylbutane-1,4-dione
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: IJGAQFBSGHWTEA-WBMJQRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯丙酮 在 正丁基锂 、 calcium chloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2S,3R)-2-hydroxy-3-methyl-1,4-diphenylbutane-1,4-dione
  参考文献：
  名称：

  Lewis Base-Promoted Aldol Reaction of Dimethylsilyl Enolates in Aqueous Dimethylformamide:  Use of Calcium Chloride as a Lewis Base Catalyst

  摘要：

  In the presence of CaCl2, dimethylsilyl (DMS) enolates smoothly reacted with aldehydes under mild conditions to give aldol adducts in good to high yields. The catalytic activities of various metal and tetrabutylammonium salts have revealed that CaCl2 works as a Lewis base catalyst to activate DMS enolates. The CaCl2-promoted reaction proceeded even in the presence of water or in pure water. This catalytic system was applicable to the aldol reaction with aqueous aldehydes such as formalin.

  DOI：

  10.1021/ja017218l

文献信息

• Highly Diastereoselective Aldol Synthesis from<i>α</i>-Iodo Ketones in Aqueous Media
  作者：Ikuya Shibata、Masatsugu Kawasaki、Makoto Yasuda、Akio Baba

  DOI：10.1246/cl.1999.689

  日期：1999.7

  Highly diastereoselective aldol synthesis from α-iodo ketones was promoted under aqueous conditions by a distannane system, (n-Bu3Sn)2, n-Bu2SnF2 and HMPA. Aqueous solutions of acetaldehyde, formaldehyde and pivaraldehyde were applicable to give β-hydroxy ketones effectively.

  在水性条件下，二锡烷系统、(n-Bu3Sn)2、n-Bu2SnF2 和 HMPA 促进了由 α-碘酮合成的高度非对映选择性羟醛。乙醛、甲醛和新戊醛的水溶液适用于有效地得到β-羟基酮。
• Highly enantioselective aza-ene-type reaction catalyzed by chiral N,N′-dioxide-nickel(ii) complex
  作者：Ke Zheng、Xiaohua Liu、Jiannan Zhao、Yang Yang、Lili Lin、Xiaoming Feng

  DOI：10.1039/b921042c

  日期：——

  An efficient catalytic enantioselective aza-ene-type reaction of glyoxal derivatives with enamides and enecarbamates has been realized using a nickel(II)-N,N'-dioxide complex as the catalyst.

  使用镍（II）-N，N'-二氧化物配合物作为催化剂，已经实现了乙二醛衍生物与酰胺和烯甲酸酯的有效催化对映选择性氮杂-烯型反应。
• Scandium trisdodecylsulfate (STDS). A new type of lewis acid that forms stable dispersion systems with organic substrates in water and accelerates aldol reactions much faster in water than in organic solvents
  作者：Shū Kobayashi、Takeshi Wakabayashi

  DOI：10.1016/s0040-4039(98)01081-8

  日期：1998.7

  A new type of Lewis acid, scandium trisdodecylsulfate (STDS), was prepared. In the presence of a catalytic amount of STDS, aldol reactions of silyl enol ethers with aldehydes proceeded smoothly in water without using any organic solvents. It was proven that stable dispersion systems including the catalyst and organic substrates were formed in water and that catalytic activity in water was much higher

  制备了一种新型的路易斯酸，三十二烷基硫酸scan（STDS）。在催化量的STDS的存在下，在不使用任何有机溶剂的情况下，甲硅烷基烯醇醚与醛的醛醇缩合反应在水中顺利进行。事实证明，在水中形成了稳定的分散体系，包括催化剂和有机底物，在水中的催化活性远高于在有机溶剂中的催化活性。据我们所知，这是路易斯酸在水中稳定分散体系中催化的第一个例子。
• Enesulfonamides as Nucleophiles in Catalytic Asymmetric Reactions
  作者：Ryosuke Matsubara、Takashi Doko、Ryosuke Uetake、Shū Kobayashi

  DOI：10.1002/anie.200605054

  日期：2007.4.20