(1S)-(-)-1-(4'-chlorophenyl)-2-phenylethanol | 650601-10-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S)-(-)-1-(4'-chlorophenyl)-2-phenylethanol
• 英文别名: (S)-1-(4-chlorophenyl)-2-phenylethanol；(1S)-1-(4-chlorophenyl)-2-phenylethanol
• CAS: 650601-10-8
• 化学式: C₁₄H₁₃ClO
• 分子量: 232.71
• InChiKey: ABRLOTURLDQJIL-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 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：
  1

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1S)-(-)-1-(4'-chlorophenyl)-2-phenylethanol 在 吡啶 作用下， 反应 16.0h， 生成 (1S)-(-)-1-(4-chlorophenyl)-2-phenylethyl acetate
  参考文献：
  名称：

  Studies on biotransformation of (±)-1-(4′-chlorophenyl)-2-phenylethanol

  摘要：

  The metabolism of (+/-)-1-4'-chlorophenyl)-2-phenylethanol 1 by the phytopathogenic fungi Colletotrichum gloeosporioides and Botrytis cinerea has been studied. Regioselective monooxygenase-catalyzed hydroxylation of C-H bonds yielded the corresponding diols, the ratios of which showed a clear preference for the C-H benzylic bond. in-Hydroxylation in the substituted aromatic ring, a rarely described phenomenon, has been observed and with good enantioselectivity. The chemistry involved ill determining the configuration of the biotransformation products is also described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.026
• 作为产物：
  描述：

  1-(4-chlorophenyl)-2-phenylethanol 在 (S)-methyl oxazaboralidine 、 Colletotrichum gloeosporioides 20122-CECT 、 Czapek-Dox medium 、 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 217.0h， 生成 (1S)-(-)-1-(4'-chlorophenyl)-2-phenylethanol
  参考文献：
  名称：

  Studies on biotransformation of (±)-1-(4′-chlorophenyl)-2-phenylethanol

  摘要：

  The metabolism of (+/-)-1-4'-chlorophenyl)-2-phenylethanol 1 by the phytopathogenic fungi Colletotrichum gloeosporioides and Botrytis cinerea has been studied. Regioselective monooxygenase-catalyzed hydroxylation of C-H bonds yielded the corresponding diols, the ratios of which showed a clear preference for the C-H benzylic bond. in-Hydroxylation in the substituted aromatic ring, a rarely described phenomenon, has been observed and with good enantioselectivity. The chemistry involved ill determining the configuration of the biotransformation products is also described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.026

文献信息

• Iridium and Rhodium Complexes Containing Enantiopure Primary Amine-Tethered <i>N</i>-Heterocyclic Carbenes: Synthesis, Characterization, Reactivity, and Catalytic Asymmetric Hydrogenation of Ketones
  作者：Kai Y. Wan、Florian Roelfes、Alan J. Lough、F. Ekkehardt Hahn、Robert H. Morris

  DOI：10.1021/acs.organomet.7b00915

  日期：2018.2.12

  a bimetallic iridium compound with (S,S)-11 as the bridging ligand. This compound contains interesting NH···Cl and NH···Ir noncovalent intramolecular interactions. Salt (S,S)-12·HPF6 reacts with silver oxide to yield [Ag2((S,S)-12)2](PF6)2 (20). Reagent 20 serves as an efficient transmetalation reagent to deliver to each rhodium in [RhCl(cod)]2 1 equiv of (S,S)-12 as a bidentate ligand to give [Rh(cod)((S

  咪唑鎓盐[（S，S）-t BuNC 3 H 3 NCHPhCHPhNH 2 ] PF 6，（S，S）-11· HPF 6是对映纯的“ Kaibene”配体t Bu-Kaibene （（S，S）-11在N-杂环卡宾（NHC）环-氮原子上具有叔丁基。通过将手性环状氨基磺酸酯与1-叔丁基咪唑回流，可以高产率和高纯度地制备它。同样（（S，S）-12·在咪唑鎓环氮原子上具有异氰酸酯基的HPF 6以相同的方式制备，并用作Mes-Kaibene，（S，S）-12的来源。这些双齿Kaibene配体具有NHC和被手性接头隔开的伯胺。盐（S，S）-11· HPF 6或（S，S）-12· HPF 6与碱和AgI或CuI反应生成总共四个M（Kaibene） 2I化合物（M = Ag或Cu）。在22°C下，胺官能化的咪唑鎓阳离子经过氧化加成到[IrCl（cod）] 2（cod = 1,5-环辛二烯）中的铱（I），生
• Enantioselective 1,2-Anionotropic Rearrangement of Acylsilane through a Bisguanidinium Silicate Ion Pair
  作者：Weidi Cao、Davin Tan、Richmond Lee、Choon-Hong Tan

  DOI：10.1021/jacs.7b13056

  日期：2018.2.7

  bisguanidinium-catalyzed tandem rearrangements of acylsilanes are reported. The acylsilanes were activated via an addition of fluoride on the silicon to form a penta-coordinate anionic silicate intermediate. The silicate then underwent alkyl or aryl group migration from the silicon atom to the neighboring carbonyl carbon atom (1,2-anionotropic rearrangement), followed by [1,2]-Brook rearrangement to provide the secondary

  报道了高度对映选择性双胍催化的酰基硅烷串联重排。通过在硅上添加氟化物来活化酰基硅烷以形成五配位阴离子硅酸盐中间体。然后硅酸盐经历烷基或芳基从硅原子迁移到相邻的羰基碳原子（1,2-阴离子重排），然后进行 [1,2]-布鲁克重排，以高产率提供具有优异对映选择性的仲醇（高达 95% ee）。α-甲硅烷基甲醇中间体的分离以及 DFT 计算表明，1,2-阴离子重排是通过双胍硅酸盐离子对发生的，这是立体确定步骤。然后通过随后的 [1,2]-布鲁克重排保留形成的手性中心而不发生反转。巴豆酰基硅烷顺利转化为高烯丙基线性巴豆醇，保留 E/Z 几何结构，未检测到支链醇。这清楚地表明 1,2-阴离子重排是通过三元而不是五元过渡态发生的。
• Asymmetric preparation of antifungal 1-(4′-chlorophenyl)-1-cyclopropyl methanol and 1-(4′-chlorophenyl)-2-phenylethanol. Study of the detoxification mechanism by Botrytis cinerea
  作者：Cristina Pinedo-Rivilla、Antonio J. Bustillo、Rosario Hernández-Galán、Josefina Aleu、Isidro G. Collado

  DOI：10.1016/j.molcatb.2011.02.005

  日期：2011.6

  Chiral alcohols are important as bioactive compounds or as precursors to such molecules. On the basis of the different antifungal properties of the enantiopure alcohol derivatives of 4'-chlorophenyl cyclopropyl ketone and benzyl 4'-chlorophenyl ketone, their enantioselective synthesis by chemical and biocatalytic methods was studied. The detoxification pathways by the phytopathogen fungus Bonytis cinerea are reported. (C) 2011 Elsevier B.V. All rights reserved.
• Preparation of Asymmetric Phase-transfer Catalyst, 1,4-Bis((4S,5S)-1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium chloride
  作者：Esther Cai Xia Ang

  DOI：10.15227/orgsyn.097.0274

  日期：——
• Studies on biotransformation of (±)-1-(4′-chlorophenyl)-2-phenylethanol
  作者：Antonio J. Bustillo、Carlos M. Garcı́a-Pajón、Josefina Aleu、Rosario Hernández-Galán、Isidro G. Collado

  DOI：10.1016/j.tetasy.2003.08.026

  日期：2003.11

  The metabolism of (+/-)-1-4'-chlorophenyl)-2-phenylethanol 1 by the phytopathogenic fungi Colletotrichum gloeosporioides and Botrytis cinerea has been studied. Regioselective monooxygenase-catalyzed hydroxylation of C-H bonds yielded the corresponding diols, the ratios of which showed a clear preference for the C-H benzylic bond. in-Hydroxylation in the substituted aromatic ring, a rarely described phenomenon, has been observed and with good enantioselectivity. The chemistry involved ill determining the configuration of the biotransformation products is also described. (C) 2003 Elsevier Ltd. All rights reserved.