(S)-1,3-diphenylhexan-1-one | 1402164-71-9

• 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: (S)-1,3-diphenylhexan-1-one
• 英文别名: (3S)-1,3-diphenylhexan-1-one
• CAS: 1402164-71-9
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: KMHGKMUWTUDYGW-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-phenylbuta-2,3-dien-1-ol 在 5-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-5H-dibenzo[b,f]azepine 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 palladium 10% on activated carbon 、 氢气 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 73.58h， 生成 (S)-1,3-diphenylhexan-1-one
  参考文献：
  名称：

  铱催化的乙烯基叠氮化物的对映选择性和化学发散性烯基烷基化合成 α-烯基酰胺和酮**

  摘要：

  使用乙烯基叠氮化物作为酰胺和酮烯醇化物替代物，通过协同铱和路易斯酸催化，实现了不稳定烯醇化物的第一次对映选择性烯丙基烷基化。利用外消旋烯丙醇作为烷基化剂，这些干燥剂控制的化学发散片段偶联反应通过动态动力学不对称转化 (DyKAT) 进行，并提供高达 >99.9 : 0.1 er 的 α-烯丙酰胺和酮

  DOI：

  10.1002/anie.202115821

文献信息

• Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts
  作者：Chunlin Wu、Guizhou Yue、Christian Duc-Trieu Nielsen、Kai Xu、Hajime Hirao、Jianrong (Steve) Zhou

  DOI：10.1021/jacs.5b11441

  日期：2016.1.27

  Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.

  亚磷酰胺的铜配合物有效地催化芳基硼试剂向无环烯酮的不对称加成。重要的是，鉴定了稀有的芳基铜（I）的 1,4-插入，这直接导致了与 O 结合的铜烯醇化物。新机制与传统的有机铜（I）在烯酮上的氧化加成/还原消除有着根本的不同。
• Catalytic Asymmetric Reductive Condensation of N-H Imines: Synthesis of<i>C</i>₂-Symmetric Secondary Amines
  作者：Vijay N. Wakchaure、Benjamin List

  DOI：10.1002/anie.201608329

  日期：2016.12.19

  A highly diastereoselective and enantioselective Brønsted acid catalyzed reductive condensation of N−H imines was developed. This reaction is catalyzed by a chiral disulfonimide (DSI), uses Hantzsch esters as a hydrogen source, and delivers useful C2‐symmetric secondary amines.

  开发了一种高度非对映选择性和对映选择性的布朗斯台德酸催化的NH亚胺的还原缩合反应。该反应由手性二磺酰亚胺（DSI）催化，使用Hantzsch酯作为氢源，并提供有用的C 2对称仲胺。
• Highly efficient synthesis of chiral aromatic ketones via Rh-catalyzed asymmetric hydrogenation of β,β-disubstituted enones
  作者：Tao Zhang、Jun Jiang、Lin Yao、Huiling Geng、Xumu Zhang

  DOI：10.1039/c7cc04045h

  日期：——

  A succinct and efficient protocol was developed for the synthesis of chiral aromatic ketones via asymmetric hydrogenation of β,β-disubstituted enones with rhodium catalysts based on chiral bisphosphine thiourea ligands. A series of substrates (17 examples) was smoothly catalyzed to afford the corresponding chiral aromatic ketones in high conversions（>99%）with excellent enantioselectivities (up to 96%

  开发了一种简洁有效的方案，用于通过基于手性双膦硫脲配体的铑催化剂对β，β-二取代的烯酮进行不对称加氢合成手性芳族酮。顺利地催化了一系列底物（17个实例），以高转化率（> 99％）和优异的对映选择性（高达96％ee）提供了相应的手性芳族酮。
• Polymer-Incarcerated Chiral Rh/Ag Nanoparticles for Asymmetric 1,4-Addition Reactions of Arylboronic Acids to Enones: Remarkable Effects of Bimetallic Structure on Activity and Metal Leaching
  作者：Tomohiro Yasukawa、Hiroyuki Miyamura、Shu̅ Kobayashi

  DOI：10.1021/ja307913e

  日期：2012.10.17

  Robust and highly active bimetallic Rh nanoparticle (NP) catalysts, PI/CB Rh/Ag have been developed and applied to the asymmetric 1,4-addition of arylboronic acids to enones without leaching of the metals. We found that the structures of the bimetallic Rh/Ag catalysts and chiral ligands strongly affect their catalytic activity and the amount of metal leaching. PI/CB Rh/Ag could be recycled several times by simple operations while keeping high yields and excellent enantioselectivities. To show the versatility of the PI/CB Rh/Ag catalyst, a one-pot, oxidation-asymmetric 1,4-addition reaction of an allyl alcohol and an arylboronic acid was demonstrated by combining the PI/CB Rh/Ag catalyst with PI/CB Au as an aerobic oxidation catalyst.