(R)-phenyl(2-(trifluoromethyl)phenyl)methanol | 143880-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-phenyl(2-(trifluoromethyl)phenyl)methanol
• 英文别名: (R)-phenyl-[2-(trifluoromethyl)phenyl]methanol
• CAS: 143880-82-4
• 化学式: C₁₄H₁₁F₃O
• 分子量: 252.236
• InChiKey: RMAICPATZGPCIL-CYBMUJFWSA-N

物化性质

• 沸点：
  321.0±37.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-[丙氨基羰酰氧基]丙酸 、 (R)-phenyl(2-(trifluoromethyl)phenyl)methanol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以66%的产率得到
  参考文献：
  名称：

  Determination of the enantiomeric excesses of chiral acids by 19F NMR studies of their esters deriving from (R)-(+)-2-(trifluoromethyl)benzhydrol

  摘要：

  15 Chiral acids were esterified with optically pure (R)-(+)-2-(trifluoromethyl)benzhydrol (R)-(+)-1, a readily available reagent. With respect to the carboxy group, the stereogenic centre is in the beta position in the case of the acids 5a-10a and 12a-16a, and in the alpha position in the case of the acids 17a-20a. The diastereomeric excesses of the corresponding esters 5b-10b and 12b-20b, respectively, were easily determined by means of F-19 NMR. These d.e. values were in very good agreement with the e.e. values of the corresponding acids when the latter were known compounds.

  DOI：

  10.1016/0957-4166(94)80154-1
• 作为产物：
  描述：

  2-(三氟甲基)二苯甲醇 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 硫酸 、 2-异丁吲哚丁醇 作用下， 反应 1.0h， 生成 (R)-phenyl(2-(trifluoromethyl)phenyl)methanol
  参考文献：
  名称：

  Determination of the enantiomeric excesses of chiral acids by 19F NMR studies of their esters deriving from (R)-(+)-2-(trifluoromethyl)benzhydrol

  摘要：

  15 Chiral acids were esterified with optically pure (R)-(+)-2-(trifluoromethyl)benzhydrol (R)-(+)-1, a readily available reagent. With respect to the carboxy group, the stereogenic centre is in the beta position in the case of the acids 5a-10a and 12a-16a, and in the alpha position in the case of the acids 17a-20a. The diastereomeric excesses of the corresponding esters 5b-10b and 12b-20b, respectively, were easily determined by means of F-19 NMR. These d.e. values were in very good agreement with the e.e. values of the corresponding acids when the latter were known compounds.

  DOI：

  10.1016/0957-4166(94)80154-1

文献信息

• Method for Asymmetric Hydrosilylation of Ketones
  申请人：Chan Albert Sun-Chi

  公开号：US20080269490A1

  公开（公告）日：2008-10-30

  Method of asymmetrically hydrosilylating substrates using catalysts having a ligand of the compound of the formula (I) wherein R is optionally substituted alkyl, cycloalkyl, aryl or heteroaryl; R′ is hydrogen, optionally substituted lower alkyl; and R″ is hydrogen, halogen, optionally substituted alkyl, hydroxy, amino (e.g., primary, secondary or tertiary), alkenyl; or an enantiomer thereof; or an enantiomeric mixture thereof with a transition metal. Particularly suitable reactions include the asymmetric hydrosilylation of ketones.

  使用具有化合物公式(I)的配体的催化剂不对称地对底物进行氢硅烷化的方法 其中 R是可选择地取代的烷基、环烷基、芳基或杂环芳基; R′是氢、可选择地取代的较低烷基; 和 R″是氢、卤素、可选择地取代的烷基、羟基、氨基(例如，一级、二级或三级)、烯基; 或其对映体; 或其与过渡金属的对映混合物。特别适合的反应包括酮的不对称氢硅烷化。
• Chiral Electron-Rich PNP Ligand with a Phospholane Motif: Structural Features and Application in Asymmetric Hydrogenation
  作者：Heng Wang、Yao Zhang、Tilong Yang、Xiaochong Guo、Quan Gong、Jialin Wen、Xumu Zhang

  DOI：10.1021/acs.orglett.0c03159

  日期：2020.11.20

  catalysts with a PNP type ligand, the electron-rich chiral PNP ligands have still been rarely reported because of the difficulties in synthesis and the nature of air-sensitivity. Herein, we report a novel chiral PNP ligand (Heng-PNP) with both a rigid backbone and a bulky tert-butyl group on the phospholane motif. We successfully obtained its divalent iron complex. The chiral environment of its Ir(III) complex

  尽管通过一系列具有PNP型配体的过渡金属催化剂实现了显着的反应性，但由于合成困难和对空气敏感的性质，富电子手性PNP配体仍然很少报道。在本文中，我们报道了一种新颖的手性PNP配体（Heng-PNP），其磷骨架上具有刚性骨架和庞大的叔丁基。我们成功获得了其二价铁配合物。还通过象限分析讨论了其Ir（III）配合物的手性环境。该三齿配体用于挑战性二芳基酮的铱催化不对称氢化反应：ee最高可达98％达到500吨。计算研究表明，底物中共轭芳基的扭曲（由Ir / Heng-PNP络合物的特殊手性口袋诱导）导致对映体确定步骤中的能量差。
• Evaluation of Enantiopure <i>N</i>-(Ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol for Catalytic Asymmetric Addition of Organozinc Reagents to Aldehydes
  作者：Min-Can Wang、Qing-Jian Zhang、Wen-Xian Zhao、Xiao-Dan Wang、Xue Ding、Tao-Tao Jing、Mao-Ping Song

  DOI：10.1021/jo701943x

  日期：2008.1.1

  catalytic asymmetric addition of organozinc reagents to aldehydes. The asymmetric ethylation, methylation, arylation, and alkynylation of aldehydes achieved enantioselectivity of up to 98.4%, 94.1%, 99.0%, and 84.6% ee, respectively, in the presence of a catalytic amount of chiral N-(ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol. Our results demonstrated further that the four-membered heterocycle-based

  从廉价且容易获得的1 -（+）-甲硫氨酸开发了一种简便实用的对映体纯的N-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇的制备方法。合成亮点包括手性氮杂环丁烷环的三步，一锅结构和一种改进的单步过程为关键中间体的合成的发展升-2-氨基-4-溴丁酸。对映纯N评估了-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇催化有机锌试剂向醛的催化不对称加成。在催化量的手性氮存在下，醛的不对称乙基化，甲基化，芳基化和炔基化分别实现了高达98.4％，94.1％，99.0％和84.6％ee的对映选择性。-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇。我们的结果进一步证明，基于四元杂环的骨架是催化不对称诱导反应的良好潜在手性单元，与苯基相比，笨重的二茂铁基的阻碍在对映选择性中发挥了重要作用。基于包括两个HOAc分子的手性配体3b的晶体结构和先前的研究，已经提出了催化不对称加成的可能过渡。
• Chiral Lithium Amido Aryl Zincates: Simple and Efficient Chemo‐ and Enantio‐Selective Aryl Transfer Reagents
  作者：Pauline Chaumont‐Olive、Mathieu Rouen、Gabriella Barozzino‐Consiglio、Amel Ben Abdeladhim、Jacques Maddaluno、Anne Harrison‐Marchand

  DOI：10.1002/anie.201813510

  日期：2019.3.4

  An enantioselective aryl transfer is promoted using chiral tricoordinated lithium amido aryl zincates that are easily accessible reagents and whose chiral appendage is simply recovered for reuse. The arylation reaction is run in good yields (60 % average on twenty substrates) and high enantiomeric excesses (95 % ee average). This occurs whatever the ortho, meta, or para substituent borne by the substrate

  使用手性三配位的酰胺基芳基锂锌酸盐手性试剂可以促进对映选择性的芳基转移，该手性试剂容易获得，其手性附属物可以简单地回收再利用。芳基化反应以高收率（在二十种底物上平均60％）和高对映体过量（95％  ee平均）进行。无论底物携带的邻位，间位或对位取代基如何发生，并且相对于醛官能团观察到完全的化学选择性。敏感的基团（例如腈，酯，酮和可松解的底物）可抵抗被测试剂的作用，从而为该方法提供了广阔的前景。
• New Enantiopure <i>N</i>-Ferrocenylmethyl Azetidin-2-yl(diphenyl)methanol and Its Application in Catalytic Asymmetric Ethylation and Arylation of Arylaldehydes
  作者：Min-Can Wang、Mao-Ping Song、Wen-Xian Zhao、Xiao-Dan Wang

  DOI：10.1055/s-2006-956474

  日期：2006.12

  A novel, facile and practical approach to preparation of new enantiopure N-ferrocenylmethyl azetidin-2-yl(diphenyl)methanol has been developed. In the presence of a catalytic amount of the chiral N-ferrocenylmethyl azetidin-2-yl(diphenyl)methanol, the enantioselective ethylation and arylation of arylaldehydes afforded addition products with enantioselectivities of up to 98.4% ee and 95.7% ee, respectively.

  我们开发了一种新颖、简便和实用的方法来制备新的对映体纯 N-二茂铁基甲基氮杂环丁烷-2-基（二苯基）甲醇。在手性 N-二茂铁基甲基氮杂环丁烷-2-基(二苯基)甲醇的催化下，芳基醛的对映体选择性乙基化和芳基化得到了加成产物，其对映体选择性分别高达 98.4% ee 和 95.7%ee。