syn-1,3-diphenyl-2-ethyl-3-hydroxypropan-1-one

• 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: syn-1,3-diphenyl-2-ethyl-3-hydroxypropan-1-one
• 英文别名: syn-2--1-phenylbutan-1-one；erythro-2-(hydroxy-phenyl-methyl)-1-phenylbutan-1-one；(2S)-2-[(S)-hydroxy(phenyl)methyl]-1-phenylbutan-1-one
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: CGPSUFGFQJIBML-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  苯甲醛 、 反式-1-苯基-2-丁烯-1-酮 在 三正丁基氢锡 、 二丁基二碘锡烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (2S,3R)-1,3-diphenyl-2-ethyl-3-hydroxy-1-propanone 、 syn-1,3-diphenyl-2-ethyl-3-hydroxypropan-1-one
  参考文献：
  名称：

  Organotin Iodide Hydride:  Chemoselective 1,4-Hydrostannations of Conjugated Enones in the Presence of Aldehydes and Subsequent Intermolecular Aldol Reactions

  摘要：

  DOI：

  10.1021/jo951500r

文献信息

• Highly enantio- and diastereoselective reductive aldol reactions catalyzed by chiral spiro bisphosphine oxides
  作者：Panke Zhang、Jiawang Liu、Zheng Wang、Kuiling Ding

  DOI：10.1016/s1872-2067(14)60241-2

  日期：2015.1

  Abstract A spiro bisphosphine oxide (SpinPO) was found to be an efficient chiral Lewis base catalyst in asymmetric reductive aldol reaction of enones and aldehydes in the presence of trichlorosilane as the reductant, affording a variety of β-hydroxyketones in good yields with moderate to high levels of diastereo- and enantioselectivities.

  摘要 在三氯硅烷作为还原剂存在下，螺环双膦氧化物 (SpinPO) 被发现是一种有效的手性路易斯碱催化剂，可用于烯酮和醛的不对称还原醛醇反应，以良好的收率提供各种 β-羟基酮。非对映选择性和对映选择性的水平。
• Synthetic control leading to chiral compounds
  作者：Teruaki Mukaiyama、Nobuharu Iwasawa、Rodney W. Stevens、Toru Haga

  DOI：10.1016/s0040-4020(01)82423-6

  日期：1984.1

  A highly diastereoselective cross aldol reaction is developed using divalent tin enolates formed from stannous trifluoromethanesulfonate and carbonyl compounds. The reaction is extended to a highly enantioselective cross aldol reaction employing chiral diamines derived from (S)-proline as ligands.

  使用由三氟甲烷磺酸亚锡和羰基化合物形成的二价烯醇锡开发了高度非对映选择性的交叉醇醛缩合反应。使用衍生自（S）-脯氨酸的手性二胺作为配体，将反应扩展至高度对映选择性的交叉羟醛反应。
• Remarkable Dependence of Diastereoselectivity on Anhydrous or Aqueous Solvent in the Indium Hydride Promoted Reductive Aldol Reaction of α,β-Unsaturated Ketones
  作者：Katsuyuki Inoue、Tatsuya Ishida、Ikuya Shibata、Akio Baba

  DOI：10.1002/1615-4169(200206)344:3/4<283::aid-adsc283>3.0.co;2-s

  日期：2002.6

  Dichloroindium hydride generated by the transmetallation between tributyltin hydride and indium trichloride predominantly reduced α,β-unsaturated ketones (enones) with 1,4-selectively even in the presence of aldehydes. Under anhydrous conditions, the successive aldol reaction between the resulting enolates and the remaining aldehydes proceeded with high anti-selectivity. The stereochemistry was dramatically

  通过三丁基氢化锡和三氯化铟之间的金属转移反应生成的氢化二氯铟即使在醛的存在下也主要用 1,4-选择性还原 α,β-不饱和酮（烯酮）。在无水条件下，所得烯醇化物和剩余醛之间的连续羟醛反应以高反选择性进行。通过分别使用水和甲醇作为添加剂和溶剂，立体化学被显着逆转为顺式选择性。
• Gazzard, Lewis J.; Motherwell, William B.; Sandham, David A., Journal of the Chemical Society. Perkin transactions I, 1999, # 8, p. 979 - 993
  作者：Gazzard, Lewis J.、Motherwell, William B.、Sandham, David A.

  DOI：——

  日期：——
• Organotin Iodide Hydride:  Chemoselective 1,4-Hydrostannations of Conjugated Enones in the Presence of Aldehydes and Subsequent Intermolecular Aldol Reactions
  作者：Takayo Kawakami、Masato Miyatake、Ikuya Shibata、Akio Baba

  DOI：10.1021/jo951500r

  日期：1996.1.1