(R)-(+)-(3-甲氧基苯基)(对甲苯基)甲醇 | 1036645-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-(+)-(3-甲氧基苯基)(对甲苯基)甲醇
• 英文名称: (R)-(+)-(3-methoxyphenyl)(p-tolyl)methanol
• 英文别名: (R)-(3-methoxyphenyl)(4-tolyl)methanol；(R)-(3-methoxyphenyl)(p-tolyl)methanol；(R)-(3-methoxyphenyl)-(4-methylphenyl)methanol
• CAS: 1036645-42-7
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: QPKHKSGBPXFYFS-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2-dimethylphenylsilyl-5-methoxyphenyl)-p-tolylmethanol 在 cesium fluoride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以98%的产率得到(R)-(+)-(3-甲氧基苯基)(对甲苯基)甲醇
  参考文献：
  名称：

  Et-duphos-nickel-catalyzed asymmetric arylation of benzaldehyde derivatives bearing an ortho-Me2PhSi group with potassium aryltriolborates

  摘要：

  The Ni-catalyzed asymmetric arylation of benzaldehydes bearing an ortho-masked H group with potassium aryltriolborates has been developed. The keys to success were (i) steric tuning of benzaldehyde derivatives with an ortho-Me2PhSi group, and (ii) the use of potassium aryltriolborates as aryl sources. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.019

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。
• 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.
• Highly enantioselective addition of arylzinc reagents to aldehydes promoted by chiral aziridine alcohols
  作者：Zuzanna Wujkowska、Szymon Jarzyński、Adam M. Pieczonka、Stanisław Leśniak、Michał Rachwalski

  DOI：10.1016/j.tetasy.2016.10.005

  日期：2016.12

  Enantiomerically pure, chiral secondary and tertiary aziridine alcohols have proven to be highly efficient catalysts for enantioselective asymmetric additions of arylzinc species to aldehydes leading to products in high chemical yields (up to 90%) and with ee's up to 90%. The influence of the stereogenic centers located at the aziridine subunit on the stereochemical course of the reaction is discussed. (C) 2016 Elsevier Ltd. All rights reserved.
• Et-duphos-nickel-catalyzed asymmetric arylation of benzaldehyde derivatives bearing an ortho-Me2PhSi group with potassium aryltriolborates
  作者：Fumie Sakurai、Kazuhiro Kondo、Toyohiko Aoyama

  DOI：10.1016/j.tetlet.2009.08.019

  日期：2009.11

  The Ni-catalyzed asymmetric arylation of benzaldehydes bearing an ortho-masked H group with potassium aryltriolborates has been developed. The keys to success were (i) steric tuning of benzaldehyde derivatives with an ortho-Me2PhSi group, and (ii) the use of potassium aryltriolborates as aryl sources. (C) 2009 Elsevier Ltd. All rights reserved.