(3R)-(-)-1,3-Diphenyl-1-heptanon | 72656-60-1

• 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: (3R)-(-)-1,3-Diphenyl-1-heptanon
• 英文别名: (3R)-1,3-diphenyl-1-heptanone；(R)-1,3-diphenyl-heptan-1-one；(R)-1,3-Diphenylheptan-1-one；(3R)-1,3-diphenylheptan-1-one
• CAS: 72656-60-1
• 化学式: C₁₉H₂₂O
• 分子量: 266.383
• InChiKey: JARDRIGVVNPARG-GOSISDBHSA-N

物化性质

• 熔点：
  36-38 °C
• 沸点：
  86 °C(Press: 0.01 Torr)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  苯硼酸 在 (S)-3,3'-dichloro-2,2'-dihydroxy-1,1'-binaphthyl 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 (S)-3-butyl-1,3-diphenyl-1-propanone 、 (3R)-(-)-1,3-Diphenyl-1-heptanon
  参考文献：
  名称：

  Binaphthol-Catalyzed Asymmetric Conjugate Arylboration of Enones

  摘要：

  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.

  DOI：

  10.1021/ol202391r

文献信息

• Asymmetric synthesis of optically active β-substituted ketones by highly enantioselective catalytic conjugate addition of dialkylzinc reagents to enones using a catalyst system of nickel(<scp>II</scp>)-chiral ligand–achiral ligand in acetonitrile/toluene
  作者：Kenso Soai、Tomoiki Hayasaka、Shoji Ugajin

  DOI：10.1039/c39890000516

  日期：——

  Highly enantioselective conjugate addition of dialkylzinc reagents to aryl substituted enones using Ni(II)-bipyridyl–chiral ligand in acetonitrile (MeCN)/toluene as an in situ prepared catalyst system affords β-substituted ketones in up to 90% enantiomeric excess (e.e.).

  使用乙腈（MeCN）/甲苯中的Ni（II）-联吡啶基-手性配体作为原位制备的催化剂体系，将二烷基锌试剂高度对映体共轭加成至芳基取代的烯酮上，得到β-取代的酮，其对映体过量高达90％（ee） 。
• Chiral Bicyclic Phosphoramidites—A New Class of Ligands for Asymmetric Catalysis
  作者：Oliver Huttenloch、Jan Spieler、Herbert Waldmann

  DOI：10.1002/1521-3765(20010202)7:3<671::aid-chem671>3.0.co;2-m

  日期：2001.2.2

  The development of new ligands for catalytic asymmetric C-C bond formation is of great interest to organic synthesis. We describe here a new class of chiral phosphoramidites that embody one or two binaphthol units attached to an achiral azabicyclic [3.3.1] or [3.3.0] framework. These ligands were easily accessible from (R)1,1'-binaphthyl-2,2'-dioxaphosphorchloridite (4) and the corresponding heterobicyclic

  用于催化不对称CC键形成的新配体的开发对有机合成非常感兴趣。我们在这里描述了一类新的手性亚磷酰胺，其包含一个或两个与非手性氮杂双环[3.3.1]或[3.3.0]骨架连接的联萘酚单元。这些配体很容易从（R）1,1'-联萘-2,2'-二氧杂磷酰氯（4）和相应的杂环双环核心1、2或3中获得。它们用于对映选择性的Cu催化的不同二烷基锌试剂的加成反应中环状和非环状烯酮。以高达91：9的对映体比例获得手性酮。事实证明，最佳配体的选择强烈依赖于每种底物。此外，发现配体6最适合α-β-不饱和酯的Rh催化氢化，
• Multinuclear Cu-Catalysts Based on SPINOL-PHOS in Asymmetric Conjugate Addition of Organozinc Reagents
  作者：Kohei Endo、Daisuke Hamada、Sayuri Yakeishi、Mika Ogawa、Takanori Shibata

  DOI：10.1021/ol300748d

  日期：2012.5.4

  Multinuclear Cu/Zn complex-catalyzed efficient asymmetric conjugate addition of organozinc reagents to acyclic and cyclic enones has been developed in the presence of a wide variety of regioisomeric chiral diols bearing phosphorus moieties as ligands. The regioisomeric SPINOL-PHOS ligands based on a SPINOL architecture showed an unexpected inversion of stereoselectivity.

  在存在多种带有磷部分作为配体的区域异构手性二醇的情况下，已经开发出有机锌试剂向无环和环状烯酮的多核Cu / Zn络合物催化的有机锌试剂的有效不对称共轭加成。基于SPINOL体系结构的区域异构SPINOL-PHOS配体表现出意想不到的立体选择性反转。
• Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents
  作者：Kohei Endo、Mika Ogawa、Takanori Shibata

  DOI：10.1002/anie.200906839

  日期：2010.3.22

  A whole lot o' metal: An efficient copper‐catalyzed asymmetric conjugate addition was achieved using a binol‐derived ligand. The catalytic system has a turnover number of 2000, and the excellent catalytic performance could be attributed to the generation of a multinuclear complex such as 1. binol=2,2′‐dihydroxy‐1,1′‐binaphthyl.

  大量金属：使用由多元醇衍生的配体实现了铜的高效催化不对称共轭物的添加。该催化系统的周转数为2000，出色的催化性能可归因于多核络合物（如1）的生成。binol = 2,2'-二羟基-1,1'-联萘基。
• Chiral lithiothiophenes as non-transferable ligands in organocuprate conjugate addition reactions
  作者：Craig A. Ogle、Jason B. Human

  DOI：10.1016/j.tetasy.2003.09.016

  日期：2003.10

  Non-transferable carbon bound homochiral ligands have been developed for the asymmetric transfer of an alkyl or an aryl group to a prochiral α,β-unsaturated enone with copper reagents. These ligands are based on thiophene and chiral amino alcohols derived from l-proline and ephedrine.

  已经开发出不可转移的碳键合的手性配体，用于用铜试剂将烷基或芳基不对称地转移到前手性α，β-不饱和烯酮上。这些配体基于噻吩和衍生自1-脯氨酸和麻黄碱的手性氨基醇。