1-(t-butylsulfinyl)-2-naphthaldehyde | 289473-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(t-butylsulfinyl)-2-naphthaldehyde
• 英文别名: (tert-butylsulfinyl)naphthaldehyde；1-(tert-butylsulfinyl)-2-naphthaldehyde；1-(2-Methylpropane-2-sulfinyl)naphthalene-2-carbaldehyde；1-tert-butylsulfinylnaphthalene-2-carbaldehyde
• CAS: 289473-08-1
• 化学式: C₁₅H₁₆O₂S
• 分子量: 260.357
• InChiKey: WBKSTDQZPNZLKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(t-butylsulfinyl)-2-naphthaldehyde 在 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 0.75h， 生成 N-(p-chlorophenyl)-1-[1-(tert-butylsulfinyl)-2-naphthyl]ethylamine
  参考文献：
  名称：

  Diastereoselective reaction of [1-(2,4,6-triisopropylphenylsulfinyl)-2-naphthyl]methanimines via diastereomeric rotamers

  摘要：

  The reactions of various (1-sulfinyl-2-naphthyl)methanimines with alkyllithium reagents were examined. Naphthylmethanimines bearing a 2,4,6-triisopropylphenylsulfinyl group gave the (R*(S), S*)-products as a single diastereomer, possibly derived from the predominant rotamer around the C-S bond axis. The reaction of chiral [1-(2,4,6-triisopropylphenylsulfinyl)-2-naphthyl]methanimine with MeLi and subsequent elimination of the sulfinyl group afforded optically active 1-(2-naphthyl)ethylamine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00379-8

文献信息

• New Asymmetric Reactions of 2-Formyl- and 2-Acyl-1-[(2,4,6-triisopropylphenyl)sulfinyl]naphthalenes via Diastereomeric Rotamers
  作者：Shuichi Nakamura、Hiroki Yasuda、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1021/jo005581p

  日期：2000.12.1

  Nucleophilic reactions with Grignard reagents and the Mukaiyama aldol reactions of the naphthaldehydes having the (2,4, 6-triisopropylphenyl)sulfinyl group produced products with high stereoselectivity. In these reactions, the stereochemistry of the major products changes depending on the Lewis acids used. Reduction of the 2-acyl-1-[(2,4,6-triisopropylphenyl)sulfinyl]naphthalenes also proceeds with

  用格氏试剂的亲核反应和具有（2,4,6-三异丙基苯基）亚磺酰基的萘醛的Mukaiyama aldol反应产生具有高立体选择性的产物。在这些反应中，主要产物的立体化学根据所使用的路易斯酸而变化。2-酰基-1-[[（2,4,6-三异丙基苯基）亚磺酰基]萘的还原也以高的立体选择性进行，但是根据还原剂的不同，其立体化学也不同。通过基于X射线晶体结构以及（1）H和（13）C NMR光谱数据的机理研究，我们证明了这些反应的极高和特定的立体选择性是由于周围的主要旋转异构体C（naph）-S轴。作为实例，提供对映体纯的2-萘甲醇的合成。
• Diastereoselective reaction of 1-(arylsulfinyl)-2-naphthaldehydes
  作者：Shuichi Nakamura、Hiroki Yasuda、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1016/s0040-4039(00)00557-8

  日期：2000.5

  Reactions of various 1-sulfinyl-2-naphthaldehydes with Grignard reagents were examined. The naphthaldehyde having the 2,4,6-triisopropylphenylsulfinyl group gave the product with high stereoselectivity, possibly derived from the predominant rotamer around the C-S axis. The reaction of the chiral sulfinylnaphthaldehyde with PhMgBr and subsequent elimination of the sulfinyl group gave the enantiomerically pure 2-naphthyl carbinol. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Diastereoselective reaction of [1-(2,4,6-triisopropylphenylsulfinyl)-2-naphthyl]methanimines via diastereomeric rotamers
  作者：Shuichi Nakamura、Hiroki Yasuda、Takeshi Toru

  DOI：10.1016/s0957-4166(02)00379-8

  日期：2002.8

  The reactions of various (1-sulfinyl-2-naphthyl)methanimines with alkyllithium reagents were examined. Naphthylmethanimines bearing a 2,4,6-triisopropylphenylsulfinyl group gave the (R*(S), S*)-products as a single diastereomer, possibly derived from the predominant rotamer around the C-S bond axis. The reaction of chiral [1-(2,4,6-triisopropylphenylsulfinyl)-2-naphthyl]methanimine with MeLi and subsequent elimination of the sulfinyl group afforded optically active 1-(2-naphthyl)ethylamine. (C) 2002 Elsevier Science Ltd. All rights reserved.