(S)-(4-chlorophenyl)(thiophen-2-yl)methanol | 1163726-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(4-chlorophenyl)(thiophen-2-yl)methanol
• 英文别名: (S)-(4-chlorophenyl)-thiophen-2-yl-methanol；(S)-(4-chlorophenyl)thiophen-2-ylmethanol；(S)-(4-chlorophenyl)-thiophen-2-ylmethanol
• CAS: 1163726-41-7
• 化学式: C₁₁H₉ClOS
• 分子量: 224.711
• InChiKey: LJVKWISXJUROPV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 4-氯苯基溴化镁 在 aluminum (III) chloride 、 双二甲胺基乙基醚 、 titanium(IV)isopropoxide 、 (R)-5,5',6,6',7,7',8,8'-八氢-[1,1'-联萘]-2,2'-二酚 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到(S)-(4-chlorophenyl)(thiophen-2-yl)methanol
  参考文献：
  名称：

  AlCl3和BDMAEE：一对有效的芳基格氏试剂和醛的高催化不对称芳构化反应活性调节剂

  摘要：

  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。

  DOI：

  10.1002/chem.201000974

文献信息

• Catalytic Enantioselective Synthesis of Diarylmethanols from Aryl Bromides and Aldehydes by Using Organolithium Reagents
  作者：Yuya Nakagawa、Yusuke Muramatsu、Toshiro Harada

  DOI：10.1002/ejoc.201001254

  日期：2010.12

  developed for preparing enantio-enriched secondary alcohols by starting from aryl bromides and aldehydes. Aryl bromides were first treated with BuLi, and the resulting aryllithium reagents were mixed with titanium tetraisopropoxide and magnesium bromide. The reaction of aldehydes with the resulting mixed titanium reagents, in the presence of 3-(3,5-diphenylphenyl)-H 8 -BINOL (2 mol-%) and titanium

  已经开发了一种从芳基溴和醛开始制备富含对映体的仲醇的通用方法。芳基溴化物首先用 BuLi 处理，所得芳基锂试剂与四异丙醇钛和溴化镁混合。在 3-(3,5-二苯基苯基)-H 8 -BINOL (2 mol-%) 和四异丙醇钛存在下，醛与所得混合钛试剂反应，以高对映选择性和高产率提供相应的醇.
• Novel Axially Chiral Phosphine Ligand with a Fluoro Alcohol Moiety for Rh-Catalyzed Asymmetric Arylation of Aromatic Aldehydes
  作者：Satoshi Morikawa、Kyosuke Michigami、Hideki Amii

  DOI：10.1021/ol100697a

  日期：2010.6.4

  A new chiral phosphine ligand (R)-1 possessing a fluoroalcohol moiety was prepared. The (R)-1-coordinated Rh(I) complex showed an excellent catalytic activity for asymmetric 1,2-addition of arylboronic acids to aldehydes to afford highly enantioenriched diarylmethanols. The fluoroalcohol moiety in ligand (R)-1 plays a pivotal role for the high enantioselectivity of the present Rh(I)-catalyzed transformation.
• 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.