(R)-4-methyl-1,3-diphenylpentan-1-one | 123673-24-5

• 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: (R)-4-methyl-1,3-diphenylpentan-1-one
• 英文别名: (3R)-4-methyl-1,3-diphenylpentan-1-one
• CAS: 123673-24-5
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: NYNGDRGORIDBPO-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  碘苯 、 (E)-4-methyl-1-phenyl-2-penten-1-one 在 乙二醇二甲醚溴化镍 、 锰 、 1-[（4S）-4-叔丁基-4,5-二氢-2-恶唑基]异喹啉 、 水 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 以91 %的产率得到(R)-4-methyl-1,3-diphenylpentan-1-one
  参考文献：
  名称：

  镍催化的对映选择性还原共轭芳基化和杂芳基化通过 1,4-加成的基本机制

  摘要：

  异喹诺酮的镍络合物直接使用芳基和杂芳基卤化物促进烯酮的对映选择性共轭芳基化和杂芳基化。该反应成功应用于ar -turmerone、(+)-tolterodine和AZD5672手性片段的立体选择性合成。从机理上讲，实验和计算支持芳基镍 (I) 络合物通过基本 1,4-加成插入到烯酮中。

  DOI：

  10.1021/jacs.2c05678

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。
• Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: <i>E</i>/<i>Z</i>-Isomerization, Regioselectivity, and Synthetic Applications
  作者：Masaharu Sugiura、Yasuhiko Ashikari、Yuka Takahashi、Koki Yamaguchi、Shunsuke Kotani、Makoto Nakajima

  DOI：10.1021/acs.joc.9b01298

  日期：2019.9.20

  The chiral bisphosphine dioxide-catalyzed asymmetric conjugate reduction of acyclic β,β-disubstituted α,β-unsaturated ketones with trichlorosilane affords saturated ketones having a stereogenic carbon center at the carbonyl β-position with high enantioselectivities. Because the E/Z-isomerizations of enone substrates occur concomitantly, reduction products with the same absolute configurations are obtained

  用三氯硅烷手性双膦二氧化物催化的无环β，β-二取代的α，β-不饱和酮的不对称共轭还原，可得到在羰基β-位具有立体碳中心且具有高对映选择性的饱和酮。因为烯酮底物会同时发生E / Z-异构化，所以从（E）-或（Z）-烯。由于其碳正离子稳定能力，在烯酮的β位上存在富电子芳基的情况下，共轭还原被加速。为了阐明观察到的对映选择性的起源，还进行了计算研究。实现了二烯酮的区域和对映选择性的还原，并将其应用于ar- turmerone，turmeronol A，mutisianthol和jungianol，它们是旋光的倍半萜烯的合成。
• Enantioselective conjugate hydrosilylation of α,β-unsaturated ketones
  作者：Huan Yang、Guanglin Weng、Dongmei Fang、Changjiang Peng、Yuanyuan Zhang、Xiaomei Zhang、Zhouyu Wang

  DOI：10.1039/c9ra01180c

  日期：——

  Enantioselective conjugate hydrosilylation of β,β-disubstituted α,β-unsaturated ketones was realized. In the presence of a chiral picolinamide–sulfonate Lewis base catalyst, the reactions provided various chiral ketones bearing a chiral center at the β-position in up to quantitative yields with moderate enantioselectivities.

  实现了β,β-二取代的α,β-不饱和酮的对映选择性共轭氢化硅烷化。在手性吡啶甲酰胺-磺酸盐路易斯碱催化剂的存在下，反应提供了各种在β位带有手性中心的手性酮，其产率高达定量，具有中等的对映选择性。
• A first high enantiocontrol of an asymmetric tertiary carbon center attached with a fluoroalkyl group via Rh(I)-catalyzed conjugate addition reaction
  作者：Tsutomu Konno、Tomoo Tanaka、Tomotsugu Miyabe、Atsunori Morigaki、Takashi Ishihara

  DOI：10.1016/j.tetlet.2008.01.122

  日期：2008.3

  Treatment of fluoroalkylated electron-deficient olefins with various boronic acids in the presence of a catalytic amount of Rh(l) coordinated with (S)-BINAP in toluene/H2O at the reflux temperature for 3 h gave the corresponding conjugate addition products with high enantioselectivity in high yields. (C) 2008 Elsevier Ltd. All rights reserved.
• Binaphthol-Catalyzed Asymmetric Conjugate Arylboration of Enones
  作者：Heather M. Turner、Jignesh Patel、Nootaree Niljianskul、J. Michael Chong

  DOI：10.1021/ol202391r

  日期：2011.11.4

  Conjugate addition of arylboronates to alpha,beta-unsaturated ketones may be catalyzed by chiral binaphthols with enantioselectivities of up to 99:1. Best results were observed with 3,3'-dichloro-BINOL. This chemistry was applied to syntheses of intermediates for syntheses of (+)-indatraline and (+)-tolterodine.