(S)-(4-fluorophenyl)(naphthalen-1-yl)methanol | 926031-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(4-fluorophenyl)(naphthalen-1-yl)methanol
• 英文别名: (S)-(4-fluorophenyl)-naphthalen-1-ylmethanol
• CAS: 926031-15-4
• 化学式: C₁₇H₁₃FO
• 分子量: 252.288
• InChiKey: YXOYRHMRZRODDL-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tris(4-fluorophenyl)aluminum 、 1-萘甲醛 在 N-甲基吗啉 、 titanium(IV) isopropylate 、 S-1,1'-联-2-萘酚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 9.5h， 以93%的产率得到(S)-(4-fluorophenyl)(naphthalen-1-yl)methanol
  参考文献：
  名称：

  廉价的添加剂N-甲基吗啉可有效降低芳基醛的催化高对映选择性芳基化反应中亲核试剂的当量。

  摘要：

  首次描述了在有效的，廉价的N-甲基吗啉存在下，由（S）-H 8 -BINOL-Ti（O i - Pr）2络合物催化的芳醛的高度对映选择性芳基化反应。我们发现对映选择性和产率很高，但与我们以前的报告相比，亲核试剂三芳基铝的当量成功降低了50％。由此大大提高了该方法的实用性。

  DOI：

  10.1002/chir.22709

文献信息

• AlCl₃and BDMAEE: A Pair of Potent Reactive Regulators of Aryl Grignard Reagents and Highly Catalytic Asymmetric Arylation of Aldehydes
  作者：Xin-Yuan Fan、Yong-Xin Yang、Fang-Fang Zhuo、Sheng-Li Yu、Xiao Li、Qi-Peng Guo、Zhi-Xue Du、Chao-Shan Da

  DOI：10.1002/chem.201000974

  日期：2010.7.19

  Cheap, energy‐saving, and applicable: With the aid of AlCl3 and BDMAEE [2,2′‐oxybis(N,N‐dimethylethanamine)], a highly asymmetric catalytic addition of various aryl Grignard reagents to aldehydes was achieved under mild conditions with easily prepared (S)‐H8‐BINOL and inexpensive commercially available Ti(OiPr)4 (see scheme), and the reaction could be easily scaled up with no loss of yield and enantioselectivity

  廉价，节能且适用：借助AlCl 3和BDMAEE [2,2'-氧双（N，N-二甲基乙胺）]，在温和条件下，将各种芳基格氏试剂高度不对称催化加成到醛中用易于制备的（S）-H 8 -BINOL和便宜的市售Ti（O i Pr）4（参见方案），该反应可以轻松扩大规模，而不会损失收率和对映选择性。
• Synthesis of new benzimidazolium salts and their application in the asymmetric arylation of aldehydes
  作者：Wei-Ping He、Bi-Hui Zhou、Ya-Li Zhou、Xiang-Rong Li、Li-Mei Fan、Hao-Wen Shou、Jie Li

  DOI：10.1016/j.tetlet.2016.06.023

  日期：2016.7

  precursor of N-heterocyclic carbene ligands, were designed and synthesized from 1,2-dibromobenzene. In situ prepared corresponding carbenes were tested in asymmetric Rh-catalyzed arylation of aromatic aldehydes, affording chiral diarylmethanols with high yields and moderate enantioselectivities.

  由1,2-二溴苯设计并合成了一系列新型的手性苯并咪唑盐，它们是N-杂环卡宾配体的前体。原位制备的相应碳烯在芳族醛的不对称Rh催化芳基化反应中进行测试，从而提供了高收率和中等对映选择性的手性二芳基甲醇。
• Development of Chiral <i>C</i>₂-Symmetric <i>N</i>-Heterocyclic Carbene Rh(I) Catalysts through Control of Their Steric Properties
  作者：Marc-Antoine Abadie、Kirsty MacIntyre、Cédric Boulho、Peter Hoggan、Frédéric Capet、Francine Agbossou-Niedercorn、Christophe Michon

  DOI：10.1021/acs.organomet.8b00823

  日期：2019.1.28

  Chiral square-planar Rh(I) complexes based on new C2-symmetric NHC ligands have been synthesized selectively in a few steps as single diastereoisomers. These chiral precatalysts were applied to the asymmetric transfer hydrogenation of 1-phenylpropanone and to the 1,2-addition of arylboronic acids to aldehydes. We demonstrated a proper functionalization of the aromatic rings connected to the nitrogen

  基于新的C 2对称NHC配体的手性方平面Rh（I）配合物已在几个步骤中选择性合成为单一非对映异构体。这些手性预催化剂被用于1-苯基丙酮的不对称转移氢化以及芳基硼酸与醛的1,2-加成反应。我们证明连接到NHC配体的氮原子的芳环的适当功能化显着改善了手性Rh（I）NHC催化剂的不对称诱导。庞大的取代基可以更好地控制催化剂象限的空间特征，因为它们表现为NHC手性骨架的构象和手性中继。
• Aryl Bromides as Inexpensive Starting Materials in the Catalytic Enantioselective Arylation of Aryl Aldehydes: The Additive TMEDA Enhances the Enantioselectivity
  作者：Yong-Xin Yang、Yue Liu、Lei Zhang、Yan-E Jia、Pei Wang、Fang-Fang Zhuo、Xian-Tao An、Chao-Shan Da

  DOI：10.1021/jo502070r

  日期：2014.11.7

  We used aryl bromides as inexpensive starting materials to enantioselectively arylate aldehydes in one pot. Aryl bromides readily transfer aryls to aryllithiums with n-butyllithium, successively to triarylaluminums with aluminum chloride, and then to aryltitaniums with titanium isopropoxide. Finally aryltitaniums arylate aldehydes catalyzed by (S)-H-8-BINOLTi(Oi-Pr)(2) in excellent yields and enantioselectivities. The additive TMEDA evidently suppresses the racemic background reaction promoted by LiCl generated from salt metathesis. This procedure represents a cost-effective and operationally convenient method for enantioenriched diarylmethanols.
• The inexpensive additive <i>N</i> -methylmorpholine effectively decreases the equivalents of nucleophiles in the catalytic highly enantioselective arylation of aryl aldehydes
  作者：Pei Wang、Yue Liu、Ya-Lun Zhang、Chao-Shan Da

  DOI：10.1002/chir.22709

  日期：2017.8

  Highly enantioselective arylation of aryl aldehydes catalyzed by (S)‐H8‐BINOL‐Ti(Oi‐Pr)2 complex in the presence of N‐methylmorpholine (NMM) as an effective and inexpensive additive is described for the first time. We found high enantioselectivity and yield but successfully reduced the equivalents of nucleophiles triarylaluminums by 50% compared with our previous report. The practicability of the process

  首次描述了在有效的，廉价的N-甲基吗啉存在下，由（S）-H 8 -BINOL-Ti（O i - Pr）2络合物催化的芳醛的高度对映选择性芳基化反应。我们发现对映选择性和产率很高，但与我们以前的报告相比，亲核试剂三芳基铝的当量成功降低了50％。由此大大提高了该方法的实用性。