(R)-1-(4-chlorophenyl)-2-phenylethanol | 811830-11-2

• 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: (R)-1-(4-chlorophenyl)-2-phenylethanol
• 英文别名: (1R)-1-(4-chlorophenyl)-2-phenylethanol
• CAS: 811830-11-2
• 化学式: C₁₄H₁₃ClO
• 分子量: 232.71
• InChiKey: ABRLOTURLDQJIL-CQSZACIVSA-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

• 作为产物：
  描述：

  (R)-1-(4-chlorophenyl)-2-phenylethyl acetate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98.8%的产率得到(R)-1-(4-chlorophenyl)-2-phenylethanol
  参考文献：
  名称：

  Asymmetric preparation of antifungal 1-(4′-chlorophenyl)-1-cyclopropyl methanol and 1-(4′-chlorophenyl)-2-phenylethanol. Study of the detoxification mechanism by Botrytis cinerea

  摘要：

  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.

  DOI：

  10.1016/j.molcatb.2011.02.005

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。
• Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement
  作者：Liang Zhang、Gabriel J. Lovinger、Emma K. Edelstein、Adam A. Szymaniak、Matteo P. Chierchia、James P. Morken

  DOI：10.1126/science.aad6080

  日期：2016.1

  Suzuki-Miyaura coupling. Specifically, we demonstrate that vinyl boronic ester ate complexes, prepared by combining organoboronates and organolithium reagents, engage in palladium-induced metallate rearrangement wherein 1,2-migration of an alkyl or aryl group from boron to the vinyl α-carbon occurs concomitantly with C–Pd σ-bond formation. This elementary reaction enables a powerful cross-coupling

  Suzuki 偶联的二合一扭曲 Suzuki-Miyaura 偶联反应是最广泛使用的制备碳-碳键的方法之一。本质上，钯催化剂激活一个碳碎片，然后将其与从硼中提取的第二个碎片连接起来。张等人。现在展示对传统途径的改变（参见 Fyfe 和 Watson 的观点）。在他们的系统中，钯最初将一个硼中心的两个碳碎片连接在一起。然后催化剂将第二个 CC 键缝合到第三个外部片段上。手性配体使反应具有高度的对映选择性。科学，这个问题 p。70; 另见第。26 钯在广泛使用的 Suzuki 偶联反应中催化硼上迁移性碳-碳键的形成。[另见 Fyfe 和 Watson 的观点] 过渡金属催化在当代有机合成中起着核心作用。考虑到非常广泛的过渡金属催化转化，值得注意的是基础元素反应步骤的数量相对较少。在这里，我们描述了许多金属催化反应中常见的有机金属金属转移步骤的替代方法，例如 Suzuki-Miyaura 偶联。
• 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：——
• 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.