1-[(R)-(4-methylphenyl)sulfinyl]naphthalene | 1669-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(R)-(4-methylphenyl)sulfinyl]naphthalene
• CAS: 1669-17-6
• 化学式: C₁₇H₁₄OS
• 分子量: 266.364
• InChiKey: INOVBEPVVYCPRK-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(R)-(4-methylphenyl)sulfinyl]naphthalene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.33h， 生成 [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 1-[(9R)-1-methyl-9H-fluoren-9-yl]naphthalene-2-carboxylate
  参考文献：
  名称：

  Asymmetric 9-(1′-naphthyl)fluorenes: enantioselective synthesis, determination of absolute configuration and retention of axial chirality in the fluorenyl carbanions

  摘要：

  通过 1-(烷基或芳基亚磺酰基)萘-2-甲酸酯与 1-甲基芴基锂的配位偶联反应，对映体选择性地合成了 1-甲基-9-[2â²-(甲氧基甲基)-1â²-萘]芴 10 和 11 的转子，并通过对 (1R)- 门酯 4 的单晶 X 射线研究确定了其绝对构型；10 和 11 的去质子化反应分别产生保留轴向手性的芴基碳离子 ent-12 和 12。

  DOI：

  10.1039/c39950002509
• 作为产物：
  描述：

  1-萘磺酰氯 生成 1-[(R)-(4-methylphenyl)sulfinyl]naphthalene
  参考文献：
  名称：

  Optically Active Sulfoxides. The Synthesis and Rotatory Dispersion of Some Diaryl Sulfoxides²

  摘要：

  DOI：

  10.1021/ja01078a047

文献信息

• Asymmetric 9-(1′-naphthyl)fluorenes: enantioselective synthesis, determination of absolute configuration and retention of axial chirality in the fluorenyl carbanions
  作者：Robert W. Baker、Trevor W. Hambley、Peter Turner

  DOI：10.1039/c39950002509

  日期：——

  The rotamers of 1-methyl-9-[2′-(methoxymethyl)-1′-naphthyl]fluorene 10 and 11 were synthesised enantioselectively via ligand coupling reactions of 1-(alkyl or arylsulfinyl)naphthalene-2-carboxylate esters with 1-methylfluorenyllithium and the absolute configurations established by a single crystal X-ray study of the (1R)-menthyl ester 4; deprotonation of 10 and 11 affords fluorenyl carbanions, ent-12 and 12, respectively, which retain axial chirality.

  通过 1-(烷基或芳基亚磺酰基)萘-2-甲酸酯与 1-甲基芴基锂的配位偶联反应，对映体选择性地合成了 1-甲基-9-[2â²-(甲氧基甲基)-1â²-萘]芴 10 和 11 的转子，并通过对 (1R)- 门酯 4 的单晶 X 射线研究确定了其绝对构型；10 和 11 的去质子化反应分别产生保留轴向手性的芴基碳离子 ent-12 和 12。
• Kinetic resolution of sulphoxides by chiral poly(N-alkyliminoalanes)
  作者：Rita Annunziata、Guido Borgogno、Fernando Montanari、Silvio Quici、Salvatore Cucinella

  DOI：10.1039/p19810000113

  日期：——

  Kinetic resolution of racemic sulphoxides by chiral poly[N-(1-phenylethyl)iminoalanes](PIA-PHETs) from (+)- or (–)-1-phenylethylamine is described. For p-tolyl mesityl sulphoxide in the temperature range between –25 and +85 °C, optical yields increase with temperature to an upper limit of between 55 and 70 °C, with enantiomeric enrichments up to ca. 75%. It is shown that, among the three molecular

  描述了由（+）-或（-）-1-苯基乙胺中的手性聚[ N-（1-苯基乙基）亚氨基丙氨酸]（PIA-PHETs）消旋亚砜的动力学拆分。对于p -甲苯基三甲苯基砜在-25和85℃之间的温度范围，光学收率随着温度增加至55和70之间上限℃，用对映体富集高达CA。75％。结果表明，在PIA-PHET的三个分子种类（闭笼四聚体，闭笼六聚体和开笼四聚体）中，只有最后一个具有化学活性并能够进行手性识别。反应遵循二级动力学（在亚砜中一级，在开放式PIA-PHET四聚体中一级）。后者的特定分子结构可能解释了高温下手性的高度识别。
• RIDLEY D. N.; SMAL M. A., J. CHEM. SOC. CHEM. COMMUN., 1981, NO 11, 505-506
  作者：RIDLEY D. N.、 SMAL M. A.

  DOI：——

  日期：——
• Sensitized photochemical switching for cholesteric liquid crystal displays
  申请人：Shukla Deepak

  公开号：US20070243342A1

  公开（公告）日：2007-10-18

  The present invention relates to photo-tunable dopant compositions comprising a photo-reactive chiral compound capable of undergoing a photochemical reaction resulting in the loss of chirality, and a triplet sensitizer. The present invention also relates to a display comprising a substrate, a liquid crystalline layer thereon, wherein the liquid crystalline layer comprises a nematic host, at least one chiral dopant, a photo-reacted compound, and a triplet sensitizer, and at least one transparent conductive layer. The present invention also relates to a method of tuning a cholesteric liquid crystal material comprising providing at least one mesogenic compound, at least one triplet sensitizer, and at least one photo-reactive chiral compound; combining the at least one mesogenic compound, at least one triplet sensitizer, and at least one photo-reactive chiral compound to form a mixture; and irradiating the mixture for a period of time.
• Sensitized Photochemical Switching for Cholesteric Liquid Crystal Displays
  申请人：Shukla Deepak

  公开号：US20100068418A1

  公开（公告）日：2010-03-18

  The present invention relates to photo-tunable dopant compositions comprising a photo-reactive chiral compound capable of undergoing a photochemical reaction resulting in the loss of chirality, and a triplet sensitizer. The present invention also relates to a display comprising a substrate, a liquid crystalline layer thereon, wherein the liquid crystalline layer comprises a nematic host, at least one chiral dopant, a photo-reacted compound, and a triplet sensitizer, and at least one transparent conductive layer. The present invention also relates to a method of tuning a cholesteric liquid crystal material comprising providing at least one mesogenic compound, at least one triplet sensitizer, and at least one photo-reactive chiral compound; combining the at least one mesogenic compound, at least one triplet sensitizer, and at least one photo-reactive chiral compound to form a mixture; and irradiating the mixture for a period of time.