(R)-(2,4-dichlorophenyl)(phenyl)methanol | 143880-83-5

• 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)-(2,4-dichlorophenyl)(phenyl)methanol
• 英文别名: (R)-(2,4-dichlorophenyl)phenyl-methanol；(R)-(2,4-dichlorophenyl)-phenylmethanol
• CAS: 143880-83-5
• 化学式: C₁₃H₁₀Cl₂O
• 分子量: 253.128
• InChiKey: KOMWHXYBCOVOGL-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4-二氯苯甲酮 在 C₆₃H₈₇Br₂N₂P₂Ru 、 potassium tert-butylate 、 氢气 作用下， 以 异丙醇 为溶剂， 40.0 ℃ 、1.01 MPa 条件下， 反应 16.0h， 以37%的产率得到
  参考文献：
  名称：

  DIPSkewphos / PICA衍生物-钌（II）配合物催化的多取代芳族酮的不对称加氢反应

  摘要：

  DIPSkewphos / PICA衍生物-Ru（II）配合物催化具有明显空间位阻的2'，3'，4'，5'，6'-五甲基苯乙酮的不对称氢化反应，在25°C下使用NaBH 4不会还原该反应，并具有底物在含碱的2-丙醇中，H 2在50个大气压下的催化剂与催化剂的摩尔比（S / C）为2000，以定量方式提供99％ee的醇。在H 2的10-50 atm下，一系列多取代的芳族酮与300 / 10,000的S / C平稳反应，生成的醇类产品的ee高达99％。该催化剂体系实现了2'，6'-二氯-3'-氟苯乙酮的工业规模加氢（50 kg），分离出的乙醇产率为96％，ee为98％。所获得的醇产物被称为合成克唑替尼的关键中间体。

  DOI：

  10.1002/cctc.201800848

文献信息

• Catalyzed asymmetric aryl transfer reactions to aldehydes with boroxines as aryl source
  作者：Xiaoyu Wu、Xinyuan Liu、Gang Zhao

  DOI：10.1016/j.tetasy.2005.06.010

  日期：2005.7

  Asymmetric aryl transfer of triphenylboroxin to a set of aryl aldehydes has been carried out in the presence of chiral amino alcohols derived from (S)-proline with high enantioselectivity. Substituted phenyl boroxins were also used as aryl source in asymmetric arylation of benzaldehyde.

  在衍生自（S）-脯氨酸的手性氨基醇的存在下，以高对映选择性进行了三苯基硼氧杂环丁烷向一组芳基醛的不对称芳基转移。在苯甲醛的不对称芳基化反应中，取代的苯基硼氧还用作芳基来源。
• Synthesis of modular thiophene-oxazoline ligands and their application in the asymmetric phenyl transfer reaction to aldehydes
  作者：Zhuo Chai、Xin-Yuan Liu、Xiao-Yu Wu、Gang Zhao

  DOI：10.1016/j.tetasy.2006.09.004

  日期：2006.9

  A series of thiophene mono (oxazoline) N,O-ligands with three sites of diversity were synthesized concisely in two steps from the corresponding thiophene carbonitriles. These ligands were applied to the enantioselective phenyl transfer reaction of aldehydes, resulting in the corresponding chiral diaryl methanol products with excellent yields and moderate to good enantioselectivities.

  从相应的噻吩腈中分两步简要合成了具有三个多样性位点的一系列噻吩单（恶唑啉）N，O-配体。将这些配体用于醛的对映选择性苯基转移反应，得到具有优异收率和中等至良好对映选择性的相应的手性二芳基甲醇产物。
• Asymmetric Hydrogenation of Polysubstituted Aromatic Ketones Catalyzed by the DIPSkewphos/PICA Derivative-Ruthenium(II) Complexes
  作者：Noriyuki Utsumi、Noriyoshi Arai、Kei Kawaguchi、Takeaki Katayama、Toshihisa Yasuda、Kunihiko Murata、Takeshi Ohkuma

  DOI：10.1002/cctc.201800848

  日期：2018.9.20

  derivative‐Ru(II) complexes catalyzed asymmetric hydrogenation of significantly sterically hindered 2’,3’,4’,5’,6’‐pentamethylacetophenone, which was not reduced with NaBH4 at 25 °C, with a substrate‐to‐catalyst molar ratio (S/C) of 2000 under 50 atm of H2 in a base‐containing 2‐propanol to afford the alcohol in 99 % ee quantitatively. A series of polysubstituted aromatic ketones was smoothly reacted

  DIPSkewphos / PICA衍生物-Ru（II）配合物催化具有明显空间位阻的2'，3'，4'，5'，6'-五甲基苯乙酮的不对称氢化反应，在25°C下使用NaBH 4不会还原该反应，并具有底物在含碱的2-丙醇中，H 2在50个大气压下的催化剂与催化剂的摩尔比（S / C）为2000，以定量方式提供99％ee的醇。在H 2的10-50 atm下，一系列多取代的芳族酮与300 / 10,000的S / C平稳反应，生成的醇类产品的ee高达99％。该催化剂体系实现了2'，6'-二氯-3'-氟苯乙酮的工业规模加氢（50 kg），分离出的乙醇产率为96％，ee为98％。所获得的醇产物被称为合成克唑替尼的关键中间体。
• Preparative synthesis of optically pure ortho-substituted benzhydrols by asymmetric reductions of the corresponding benzophenones
  作者：Eric Brown、Antoine Lézé、Joël Touet

  DOI：10.1016/s0957-4166(00)82179-5

  日期：1992.7

  Lithium aluminium hydride previously treated with 2.5 equivalents of (S)-(+) or (R)-(-)-2 -(2-iso-indolinyl)butan-1-ol 3 (readily available reagents) reduced the five ortho-substituted benzophenones 4-6, 8 and 10 into the corresponding optically active benzhydrols with nearly 100% enantiomeric excesses. Other examples of asymmetric reductions of prochiral benzophenones are given.
• Axially chiral C2-symmetric N-heterocyclic carbene (NHC) palladium complexes-catalyzed asymmetric arylation of aldehydes with arylboronic acids
  作者：Rui Zhang、Qin Xu、Xiuchun Zhang、Tao Zhang、Min Shi

  DOI：10.1016/j.tetasy.2010.06.041

  日期：2010.8

  Chiral C-2-symmetric N-heterocyclic carbene (NHC) palladium diaquo complexes 5a-c and the chiral C-2-symmetric NHC-palladium complexes 5d and 5e prepared from (R)-BINAM or H-8-(R)-BINAM could be used as the catalysts for the enantioselective arylation of arylaldehydes with arylboronic acids in which NHC-Pd complex 5a was found to be fairly effective in this reaction to give the corresponding adducts in moderate enantioselectivities along with moderate to good yields. (C) 2010 Elsevier Ltd. All rights reserved.