α-[(1S,3R)-3-hydroxy-2,2,3-trimethylcyclopentyl]-α-phenylbenzenemethanol | 461389-03-7

• 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: α-[(1S,3R)-3-hydroxy-2,2,3-trimethylcyclopentyl]-α-phenylbenzenemethanol
• CAS: 461389-03-7
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: YJKVLSJNIOENRW-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  四氢呋喃 、 二异丙氧基二氯化钛 、 乙腈 、 α-[(1S,3R)-3-hydroxy-2,2,3-trimethylcyclopentyl]-α-phenylbenzenemethanol 以 乙腈 为溶剂， 生成 (acetonitrile)dichloro[α-(1S,3R)-3-(oxylato-κO)-2,2,3-trimethylcyclopentyl-α-phenylbenzenemethanolato(2-)-κO](tetrahydrofuran)titanium-acetonitrile
  参考文献：
  名称：

  TitaniumLewis Acids for Asymmetric Catalysis: Synthesis and Structural Characterization of Dichloro[diolato(2−)-κO,κO′]bis(solvent)titanium ([TiCl2(diolato)(solvent)2]) Complexes

  摘要：

  The complexes [TiCl2{(R,R)-TADDOLato}(DME)](MeCN)-Me-. (3), and [TiCl2{(R,R)-1-Nph-TADDOL-ato}(McCN)(2)](CH2Cl2)-C-. (4b) (DME 1,2-dimethoxyethane; (R,R)-TADDOLato = (4R,5R)-2,2-dimethyl-a,a,a',a'-tetraphenyl-1,3-dioxotane-4,5-dimethanolato(2 (2-)-kappaO,kappaO'; (R,R)-1-Nph-TADDOLato = (4R,5R)2,2-dimethyl-a,a,a',a'-tetra(naphthalen-1-yl)-1,3-dioxotane-4,5-dimethanolato(2-)-kappaO,kappaO') were prepared and isolated in high yield as stable crystalline materials (Scheme 1). They constitute ideally suited and easy-to-handle catalyst precursors for a large number of Ti-catalyzed asymmetric reactions, for which they have been previously generated in situ. The X-ray crystal structures of 3 and 4b show a distorted octahedral geometry around Ti with the chloro ligands in mutual trans positions (Figs. 5 and 6). The new chiral diols a-(1S,3R)-3-hydroxy-2,2,3-trimethylcyclopentyl]-a-phenylbenzenemethanol (13a), derived from camphoric acid (5), and (M) -6,6'-dimethyl-a,a,a',a'-tetraphenyl[1,1'-biphenyl]-2,2'-dimethanol (15) were prepared (Schemes 3 and 4). These new ligands are able to form mononuclear complexes with the (TiCl2)-Cl-IV, fragment. The corresponding complex 14 derived front 13a was characterized by X-ray as a mixed THF/MeCN adduct.

  DOI：

  10.1002/1522-2675(200206)85:6<1597::aid-hlca1597>3.0.co;2-n
• 作为产物：
  描述：

  D-樟脑酸 、 phenylmagnesium bromide 在 lead(IV) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 以51.3%的产率得到α-[(1S,3R)-3-hydroxy-2,2,3-trimethylcyclopentyl]-α-phenylbenzenemethanol
  参考文献：
  名称：

  TitaniumLewis Acids for Asymmetric Catalysis: Synthesis and Structural Characterization of Dichloro[diolato(2−)-κO,κO′]bis(solvent)titanium ([TiCl2(diolato)(solvent)2]) Complexes

  摘要：

  The complexes [TiCl2{(R,R)-TADDOLato}(DME)](MeCN)-Me-. (3), and [TiCl2{(R,R)-1-Nph-TADDOL-ato}(McCN)(2)](CH2Cl2)-C-. (4b) (DME 1,2-dimethoxyethane; (R,R)-TADDOLato = (4R,5R)-2,2-dimethyl-a,a,a',a'-tetraphenyl-1,3-dioxotane-4,5-dimethanolato(2 (2-)-kappaO,kappaO'; (R,R)-1-Nph-TADDOLato = (4R,5R)2,2-dimethyl-a,a,a',a'-tetra(naphthalen-1-yl)-1,3-dioxotane-4,5-dimethanolato(2-)-kappaO,kappaO') were prepared and isolated in high yield as stable crystalline materials (Scheme 1). They constitute ideally suited and easy-to-handle catalyst precursors for a large number of Ti-catalyzed asymmetric reactions, for which they have been previously generated in situ. The X-ray crystal structures of 3 and 4b show a distorted octahedral geometry around Ti with the chloro ligands in mutual trans positions (Figs. 5 and 6). The new chiral diols a-(1S,3R)-3-hydroxy-2,2,3-trimethylcyclopentyl]-a-phenylbenzenemethanol (13a), derived from camphoric acid (5), and (M) -6,6'-dimethyl-a,a,a',a'-tetraphenyl[1,1'-biphenyl]-2,2'-dimethanol (15) were prepared (Schemes 3 and 4). These new ligands are able to form mononuclear complexes with the (TiCl2)-Cl-IV, fragment. The corresponding complex 14 derived front 13a was characterized by X-ray as a mixed THF/MeCN adduct.

  DOI：

  10.1002/1522-2675(200206)85:6<1597::aid-hlca1597>3.0.co;2-n

文献信息

• TitaniumLewis Acids for Asymmetric Catalysis: Synthesis and Structural Characterization of Dichloro[diolato(2−)-κO,κO′]bis(solvent)titanium ([TiCl2(diolato)(solvent)2]) Complexes
  作者：Lukas Hintermann、Diego Broggini、Antonio Togni

  DOI：10.1002/1522-2675(200206)85:6<1597::aid-hlca1597>3.0.co;2-n

  日期：2002.6

  The complexes [TiCl2(R,R)-TADDOLato}(DME)](MeCN)-Me-. (3), and [TiCl2(R,R)-1-Nph-TADDOL-ato}(McCN)(2)](CH2Cl2)-C-. (4b) (DME 1,2-dimethoxyethane; (R,R)-TADDOLato = (4R,5R)-2,2-dimethyl-a,a,a',a'-tetraphenyl-1,3-dioxotane-4,5-dimethanolato(2 (2-)-kappaO,kappaO'; (R,R)-1-Nph-TADDOLato = (4R,5R)2,2-dimethyl-a,a,a',a'-tetra(naphthalen-1-yl)-1,3-dioxotane-4,5-dimethanolato(2-)-kappaO,kappaO') were prepared and isolated in high yield as stable crystalline materials (Scheme 1). They constitute ideally suited and easy-to-handle catalyst precursors for a large number of Ti-catalyzed asymmetric reactions, for which they have been previously generated in situ. The X-ray crystal structures of 3 and 4b show a distorted octahedral geometry around Ti with the chloro ligands in mutual trans positions (Figs. 5 and 6). The new chiral diols a-(1S,3R)-3-hydroxy-2,2,3-trimethylcyclopentyl]-a-phenylbenzenemethanol (13a), derived from camphoric acid (5), and (M) -6,6'-dimethyl-a,a,a',a'-tetraphenyl[1,1'-biphenyl]-2,2'-dimethanol (15) were prepared (Schemes 3 and 4). These new ligands are able to form mononuclear complexes with the (TiCl2)-Cl-IV, fragment. The corresponding complex 14 derived front 13a was characterized by X-ray as a mixed THF/MeCN adduct.