1-naphthalen-2-yl-1-thiophen-2-yl-ethanol | 1176196-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-naphthalen-2-yl-1-thiophen-2-yl-ethanol
• 英文别名: 1-Naphthalen-2-yl-1-thiophen-2-ylethanol
• CAS: 1176196-28-3；356555-73-2
• 化学式: C₁₆H₁₄OS
• mdl: MFCD03211851
• 分子量: 254.353
• InChiKey: JXKIVTUSEAKSOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.125
• 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：

  Al(2-thienyl)3(OEt2) 、 2-萘乙酮 在 四氢呋喃 、 titanium(IV) isopropylate 、 S-1,1'-联-2-萘酚 作用下， 以 甲苯 为溶剂， 反应 24.17h， 以94%的产率得到1-naphthalen-2-yl-1-thiophen-2-yl-ethanol
  参考文献：
  名称：

  Direct Asymmetric Catalytic Thienylaluminum Addition to Ketones: A Concise Approach to the Synthesis of (S)-Tiemonium Iodide

  摘要：

  A direct asymmetric addition of a (2-thienyl)aluminum reagent to ketones catalyzed by a titanium catalyst of (S)-BINOL to afford chiral tertiary 2-thienyl alcohols is reported. The catalytic system works excellently for aromatic ketones and for 1-acetylcyclohexene, furnishing products in excellent enantioselectivities of up to 97% ee. However, the additions to dialkyl ketones afford products in low enantioselectivities of 8-17% ee. Importantly, a concise 3-step synthesis of (S)-tiemonium iodide with an 84% yield is demonstrated.

  DOI：

  10.1021/ol901193q

文献信息

• Direct Asymmetric Catalytic Thienylaluminum Addition to Ketones: A Concise Approach to the Synthesis of (<i>S</i>)-Tiemonium Iodide
  作者：Deepak B. Biradar、Shuangliu Zhou、Han-Mou Gau

  DOI：10.1021/ol901193q

  日期：2009.8.6

  A direct asymmetric addition of a (2-thienyl)aluminum reagent to ketones catalyzed by a titanium catalyst of (S)-BINOL to afford chiral tertiary 2-thienyl alcohols is reported. The catalytic system works excellently for aromatic ketones and for 1-acetylcyclohexene, furnishing products in excellent enantioselectivities of up to 97% ee. However, the additions to dialkyl ketones afford products in low enantioselectivities of 8-17% ee. Importantly, a concise 3-step synthesis of (S)-tiemonium iodide with an 84% yield is demonstrated.