(R)-(+)-(2-hydroxy-3,3,3-trifluoropropyl)phenyl ketone | 108535-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-(2-hydroxy-3,3,3-trifluoropropyl)phenyl ketone
• 英文别名: (R)-(+)-3,3,3-trifluoro-2-hydroxypropyl phenyl ketone；(R)-4,4,4-trifluoro-3-hydroxy-1-phenyl-1-butanone；(R)-4,4,4-trifluoro-3-hydroxy-1-phenylbutan-1-one；(R)-beta-Hydroxy-gamma,gamma,gamma-trifluorobutyrophenone；(3R)-4,4,4-trifluoro-3-hydroxy-1-phenylbutan-1-one
• CAS: 108535-35-9
• 化学式: C₁₀H₉F₃O₂
• 分子量: 218.175
• InChiKey: LGRAOIBBJUNFDG-SECBINFHSA-N

物化性质

• 熔点：
  41.0-42.0 °C
• 沸点：
  306.8±42.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(+)-(2-hydroxy-3,3,3-trifluoropropyl)phenyl ketone 生成 (2R,4Z)-1,1,1-trifluoro-4-hydroxyimino-4-phenylbutan-2-ol
  参考文献：
  名称：

  KITASUMEH, TOMOYA

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-butyldimethyl(1-phenylvinyloxy)silane 在 (R)-binaphthol-derived titanium complex 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (R)-(+)-(2-hydroxy-3,3,3-trifluoropropyl)phenyl ketone
  参考文献：
  名称：

  Asymmetric Catalytic Friedel−Crafts Reaction of Silyl Enol Ethers with Fluoral:  A Possible Mechanism of the Mukaiyama-Aldol Reactions

  摘要：

  [GRAPHICS]The catalytic asymmetric Friedel-Crafts reaction of silyl enol ethers with fluoral proceeds under Mukaiyama-aldol conditions to give silyl enol ether products. The sequential diastereoselective reactions of the resultant silyl enol ethers with electrophiles provide highly enantiopure functionalized organofluorine compounds of material and pharmaceutical interest.

  DOI：

  10.1021/ol990330s

文献信息

• Ru-Catalyzed Chemo- and Enantioselective Hydrogenation of β-Diketones Assisted by the Neighboring Heteroatoms
  作者：Wanfang Li、Bin Lu、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/acs.orglett.9b01829

  日期：2019.7.19

  A highly chemo- and enantioselective hydrogenation of β-diketones was achieved by using [Ru(benzene)(S)-SunPhosCl]Cl for consistency in THF. The neighboring heteroatoms played important roles in guaranteeing the reactivity and controlling the chemoselectivity. These results suggested a potential approach for the clean and facile synthesis of functionalized chiral β-hydroxy ketones, which could otherwise

  通过使用[Ru（苯）（S）-SunPhosCl] Cl在THF中的稠度，可以实现β-二酮的高度化学和对映选择性氢化。相邻的杂原子在保证反应性和控制化学选择性方面起着重要作用。这些结果暗示了清洁和容易地合成官能化的手性β-羟基酮的潜在方法，该方法可以通过少得多的步骤经济转化来制备。
• Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts
  作者：Paola Vitale、Filippo Maria Perna、Gennaro Agrimi、Antonio Scilimati、Antonio Salomone、Cosimo Cardellicchio、Vito Capriati

  DOI：10.1039/c6ob02320g

  日期：——

  could then be diastereoselectively transformed into optically active syn- or anti-1,3-diols by a careful choice of the chemical reducing agent (diastereomeric ratio up to 98 : 2). The latter, in turn, were stereospecifically cyclized into the corresponding oxetanes in 43–98% yields and in up to 94% ee, thereby giving a diverse selection of stereo-defined 2,4-disubstituted aryloxetanes.

  在不同的全细胞微生物存在下研究了取代的1,3-芳基二酮的区域和立体选择性还原，发现该化合物可提供非常好的收率（高达95％）和对映异构体的β-羟基酮或1,3-二醇多余（高达96％）。可以通过面包酵母和罗伊氏乳杆菌DSM 20016生物还原以相反的立体偏好获得的对映体富集的醛醇，可以非对映选择性地转化为光学活性的顺式或反式-1,3-二醇可通过仔细选择化学还原剂（非对映异构体比例最高为98：2）来实现。后者依次以43-98％的收率和高达94％ee的立体定向环化成相应的氧杂环丁烷，从而提供了多种立体定义的2,4-二取代芳基氧杂环丁烷选择。
• Chiral Bipyridine Ligand with Flexible Molecular Recognition Site: Development and Application to Copper‐Catalyzed Asymmetric Borylation of α,β‐Unsaturated Ketones
  作者：Ryosuke Tsutsumi、Rika Taguchi、Masahiro Yamanaka

  DOI：10.1002/cctc.202101278

  日期：2022.1.21

  Asymmetric Catalysis: A novel chiral bipyridine ligand with a flexible hydrogen-bond donor was developed based on the TS-stabilization concept. This designed chiral bipyridine ligand was applied to the copper-catalyzed asymmetric borylation of a wide range of α,β-unsaturated ketones, affording the borylated products in high yields with high enantioselectivities. The potential of a high-level control

  不对称催化：基于 TS 稳定概念开发了一种具有柔性氢键供体的新型手性联吡啶配体。这种设计的手性联吡啶配体被应用于铜催化的各种 α,β-不饱和酮的不对称硼化反应，以高产率和高对映选择性提供硼化产物。还证明了对化学选择性和立体选择性进行高级控制的潜力。
• <i>C</i>₂-Symmetric Chiral Bisoxazolines as Hydrogen-Bond-Acceptor Catalysts in Enantioselective Aldol Reaction of β-Carbonyl Acids with Trifluoroacetaldehyde Hemiacetals
  作者：Zhen-Yan Yang、Jun-Liang Zeng、Nan Ren、Wei Meng、Jing Nie、Jun-An Ma

  DOI：10.1021/acs.orglett.6b03256

  日期：2016.12.16

  C2-symmetric chiral bisoxazoline is demonstrated to use hydrogen bonding to catalyze an important family of aldol reactions of trifluoroacetaldehyde hemiacetals with various β-carbonyl acids. This reaction is highly enantioselective, delivering chiral nonracemic trifluoromethylated alcohols with excellent optical purity and good isolated yields. This concept of relaying chiral information via a chiral hydrogen-bond

  一个简单的C 2对称手性双恶唑啉被证明使用氢键催化三氟乙醛半缩醛与各种β-羰基酸的重要的醛醇缩合反应家族。该反应是高度对映体选择性的，以优异的光学纯度和良好的分离产率提供手性非外消旋三氟甲基化醇。通过手性氢键受体传递手性信息的概念应适用于大量的有机催化过程。
• Development of copper-catalyzed enantioselective decarboxylative aldolization for the preparation of perfluorinated 1,3,5-triols featuring supramolecular recognition properties
  作者：Céline Sperandio、Jean Rodriguez、Adrien Quintard

  DOI：10.1039/c9sc05196a

  日期：——

  properties to organic molecules but the scarcity of natural organofluorine sources renders the development of new synthetic methods highly desirable. Using a chiral BOX/Cu combination, enantioselective decarboxylative aldolization of perfluorinated aldehydes has been developed. Most notably, the reaction occurring under mild conditions and with high enantiocontrol can create ketodiols in one single synthetic

  氟能够赋予有机分子独特的性质，但天然有机氟来源的稀缺使得开发新的合成方法非常迫切。使用手性 BOX/Cu 组合，开发了全氟醛的对映选择性脱羧醛醇缩反应。最值得注意的是，在温和条件下发生的反应具有高对映体控制，可以在一次合成操作中产生酮二醇，这是关键的全氟化 1,3,5-三醇的前体。此外，与三氯乙醛进行的反应验证了所提出的基于空间相互作用的过渡态模型，并提供了具有巨大合成实用性的六氯化酮二醇的第一个对映选择性合成。全氟化1,3,5-三醇形成中心氢键框架的能力允许阴离子的强配位，并且通过催化剂控制的合成序列获得的手性证明了多元醇的选择性手性阴离子识别能力。