(S)-naphthalen-1-yl(p-tolyl)methanol | 1002328-13-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-naphthalen-1-yl(p-tolyl)methanol
• 英文别名: (S)-(4-methylphenyl)-naphthalen-1-ylmethanol
• CAS: 1002328-13-3
• 化学式: C₁₈H₁₆O
• 分子量: 248.324
• InChiKey: LORGQLQYAZLTMF-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  naphthalen-1-yl(p-tolyl)methanone 在 C₈₄H₈₀Cl₄N₂O₂P₄Ru₃ 、 氢气 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 10.0 ℃ 、4.0 MPa 条件下， 以97 %的产率得到(S)-naphthalen-1-yl(p-tolyl)methanol
  参考文献：
  名称：

  RuPHOX-Ru 催化不对称氢化合成手性二芳基甲醇

  摘要：

  已经建立了 RuPHOX-Ru 催化的二芳基酮不对称氢化，以高达 99% 的产率和 99% ee 提供相应的手性二芳基甲醇。该方案可以在催化剂负载量相对较低 (2000 S/C) 的克规模上进行，所得产品可进行多种有用的转化，特别是用于手性药物的合成，例如 ( S ) -Orphenadrine和( S )-新苯二甲酸。氘标记和对照实验表明，RuPHOX-Ru 催化的不对称氢化完全以 H 2作为唯一氢源进行氢化。

  DOI：

  10.1002/adsc.202300213

文献信息

• The concise synthesis of chiral tfb ligands and their application to the rhodium-catalyzed asymmetric arylation of aldehydes
  作者：Takahiro Nishimura、Hana Kumamoto、Makoto Nagaosa、Tamio Hayashi

  DOI：10.1039/b911118b

  日期：——

  New C2-symmetric tetrafluorobenzobarrelene ligands were prepared and applied successfully to the rhodium-catalyzed asymmetric addition of arylboronic acids to aromatic aldehydes giving chiral diarylmethanols in high yield with high enantioselectivity.

  制备了新的C2对称的四氟苯并戊烯配体，并将其成功地用于铑催化的芳基硼酸向芳族醛的不对称加成反应，从而以高收率和高对映体选择性得到手性二芳基甲醇。
• 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。
• 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。
• Diarylmethanols by Catalyzed Asymmetric Aryl Transfer Reactions onto Aldehydes Using Boronic Acids as Aryl Source
  作者：Frank Schmidt、Jens Rudolph、Carsten Bolm

  DOI：10.1002/adsc.200600390

  日期：2007.3.5

  Using a planar-chiral ferrocene as catalyst and combinations of functionalized aldehydes and substituted arylboronic acids as starting materials, asymmetric aryl transfer reactions give access to structurally diverse, optically active diarylmethanols in high yields and enantioselectivities.

  使用平面手性二茂铁作为催化剂，并结合官能化的醛和取代的芳基硼酸作为起始原料，不对称的芳基转移反应可以以高收率和对映选择性获得结构多样的旋光性二芳基甲醇。
• 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.