(2S,2'S)-oxybis(propane-2,1-diyl)bis(4-methylbenzenesulfonate) | 171753-73-4

• 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: (2S,2'S)-oxybis(propane-2,1-diyl)bis(4-methylbenzenesulfonate)
• 英文别名: [(2S)-2-[(2S)-1-(4-methylphenyl)sulfonyloxypropan-2-yl]oxypropyl] 4-methylbenzenesulfonate
• CAS: 171753-73-4
• 化学式: C₂₀H₂₆O₇S₂
• 分子量: 442.554
• InChiKey: BKKNILNYOJKUJE-ROUUACIJSA-N

物化性质

• 沸点：
  587.7±45.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,2'S)-oxybis(propane-2,1-diyl)bis(4-methylbenzenesulfonate) 在 ammonium cerium(IV) nitrate 、 sodium hydride 、 氟硼酸钾 、 乙硫醇 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 52.0h， 生成 (5S,8S,10S,13S)-8,10-Dimethyl-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17-diene-19,21-dione
  参考文献：
  名称：

  Preparation of optically active azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: temperature-dependent enantiomer selectivity in the complexation with chiral amines 1

  摘要：

  采用(2S,4S)-2,4-二甲基-3-氧戊烷-1,5-二醇和(S)-或(R)-1-苯乙烷-1,2-二醇作为手性子单元，合成了具有两个苯基和两个甲基取代基以及p-(2,4-二硝基苯基偶氮)酚基团的光学活性偶氮酚类冠醚(S,S,S,S)-1、(R,S,S,R)-2、(S,S,S,S)-3和(R,S,S,R)-4，并且这些化合物以对映体纯形式制备。通过在氯仿中采用紫外-可见光光谱法研究了这些冠醚与手性胺的复合过程中温度依赖的对映选择性，并根据观察到的结合常数计算了复合的热力学参数。

  DOI：

  10.1039/a703452k
• 作为产物：
  描述：

  2-[(2S)-1-phenylmethoxypropan-2-yl]oxypropan-1-ol 在 palladium on activated charcoal 吡啶 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 生成 (2S,2'S)-oxybis(propane-2,1-diyl)bis(4-methylbenzenesulfonate)
  参考文献：
  名称：

  Preparation of optically active azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: temperature-dependent enantiomer selectivity in the complexation with chiral amines 1

  摘要：

  采用(2S,4S)-2,4-二甲基-3-氧戊烷-1,5-二醇和(S)-或(R)-1-苯乙烷-1,2-二醇作为手性子单元，合成了具有两个苯基和两个甲基取代基以及p-(2,4-二硝基苯基偶氮)酚基团的光学活性偶氮酚类冠醚(S,S,S,S)-1、(R,S,S,R)-2、(S,S,S,S)-3和(R,S,S,R)-4，并且这些化合物以对映体纯形式制备。通过在氯仿中采用紫外-可见光光谱法研究了这些冠醚与手性胺的复合过程中温度依赖的对映选择性，并根据观察到的结合常数计算了复合的热力学参数。

  DOI：

  10.1039/a703452k

文献信息

• Betti's base for crystallization-induced deracemization of substituted aldehydes: synthesis of enantiopure amorolfine and fenpropimorph
  作者：Andrea Carella、Gabriel Ramos Ferronatto、Emanuela Marotta、Andrea Mazzanti、Paolo Righi、Claudio Paolucci

  DOI：10.1039/c6ob02765b

  日期：——

  diastereoisomer transformation (CIDT) of naphthoxazines derived from racemic O-protected 2-substituted 4-hydroxybutyraldehydes and enantiopure Betti's base allows the deracemization of the starting aldehydes with ee up to 96%. As an alternative, reduction with lithium aluminum hydride of the diastereoisomerically enriched naphthoxazines leads to enantioenriched primary amines. The utility of the latter strategy

  由外消旋的O-保护的2-取代的4-羟基丁醛和对映体纯的Betti's碱衍生的萘并恶嗪的酸促进结晶诱导的非对映异构体转化（CIDT）可以使起始醛与ee的反硝化作用高达96％。或者，用氢化锂铝将非对映异构体富集的萘并恶嗪还原可得到对映体富集的伯胺。后一种方法的实用性通过将其应用于对映体富集的苯丙咪唑和ee高达99.5％的对映体纯阿莫罗芬的首次合成得到了证明。
• Preparation of homochiral azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: Enantiomer recognition behaviour towards chiral 2-aminoethanol derivatives
  作者：Koichiro Naemura、Kazuko Ogasahara、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/s0957-4166(96)00472-7

  日期：1997.1

  Enantiomerically pure azophenolic crown ethers 1–4 containing (S)- or (R)-1-phenylethane-1,2-diol moieties and (2S,4S)-2,4-dimethyl-3-oxapentane-1,5-diol moiety as a chiral subunit were prepared; crown ethers (S,S,S,S)-1 showed high chiral recognition behaviour in complexation with 2-substituted 2-aminoethanol derivatives.

  对映体纯的偶氮酚冠醚1-4，含有（S）-或（R）-1-苯基乙烷-1,2-二醇部分和（2 S，4 S）-2,4-二甲基-3-氧杂戊烷-1,5制备了作为手性亚基的-二醇部分；冠醚（S，S，S，S）-1在与2-取代的2-氨基乙醇衍生物络合中显示出高手性识别行为。
• Compounds and compositions as inhibitors of endosomal toll-like receptors
  申请人：Novartis AG

  公开号：US10954233B2

  公开（公告）日：2021-03-23

  The invention disclosed herein relates to 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridinyl compounds and 4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridinyl compounds of Formula (A), pharmaceutical compositions comprising such compounds and the use of such compounds in the treatment of autoimmune diseases.

  本发明涉及式（A）的4,5,6,7-四氢-1H-吡唑并[4,3-c]吡啶基化合物和4,5,6,7-四氢-2H-吡唑并[4,3-c]吡啶基化合物、包含此类化合物的药物组合物以及此类化合物在治疗自身免疫性疾病中的用途。
• Visual Enantiomeric Recognition of Amino Acid Derivatives in Protic Solvents¹^,
  作者：Kazunori Tsubaki、Daisuke Tanima、Mohammad Nuruzzaman、Tomokazu Kusumoto、Kaoru Fuji、Takeo Kawabata

  DOI：10.1021/jo050387u

  日期：2005.6.1

  [GRAPHICS]Various types of chiral host molecules 2-7 based on a phenolphthalein skeleton and two crown ethers were prepared for use in visual enantiomeric recognition, and we examined their enantioselective coloration in complexation with chiral amino acid derivatives 9-22 in methanol solution. Methyl-substituted host (S,S,S,S)-3 showed particularly prominent enantiomer selectivity for the alanine amide derivatives 11 and 12. A combination of methyl-substituted host (S,S,S,S)-3 with guest (R)-11 or (R)-12 developed a purple color, whereas no color development was observed with (S)-11 or (S)-12. On the other hand, phenyl-substituted host (S,S,S,S)-6 showed deeper coloration with a wide range of (S)-beta-amino alcohols compared to that seen with host (S,S,S,S)-6 and the corresponding (R)-beta-amino alcohols at 0 degrees C. Furthermore, absorbance inversion temperatures (AIT) were observed within the range of 0-50 degrees C in many cases.
• Preparation and enantiomer recognition of chiral azophenolic crown ethers having three chiral barriers on each of the homotopic faces
  作者：Koichiro Naemura、Masaki Asada、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/0957-4166(95)00240-p

  日期：1995.8

  Homochiral azophenolic crown ethers 1 and 2 having three chiral barriers, that is, the phenyl group, the methyl group, and the cyclohexane moiety on each of the homotopic faces have been prepared. The enantiomer recognition toward chiral 2-aminoethanol derivatives has been examined.