2-(4-丁一氧代丁氧基)乙醇 | 168784-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 2-(4-丁一氧代丁氧基)乙醇
• 英文名称: (R)-(-)-4,4'-biphenanthrene-3,3'-dithiol
• 英文别名: 4,4'-biphenanthrene-3,3'-dithiol；4-(3-Sulfanylphenanthren-4-yl)phenanthrene-3-thiol
• CAS: 168784-27-8；170172-95-9；170173-00-9
• 化学式: C₂₈H₁₈S₂
• 分子量: 418.583
• InChiKey: LPBLBTFPQIOZDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-丁一氧代丁氧基)乙醇 以 二氯甲烷 为溶剂， 生成 Rh2(μ-4,4'-biphenanthrene-3,3'-dithiolate)(CO)4
  参考文献：
  名称：

  [Rh 2（μ- biphes）（cod）2 ]（H 2 biphes = 4,4'-biphenanthrene-3,3'- dithiol）的不对称加氢甲酰化X射线结构中具有阻转异构硫配体的金属配合物

  摘要：

  将阻转异构的外消旋硫化合物4,4'-联菲-3,3'-二硫醇（H 2 biphes）添加到[{M（μ- OMe）（cod）} 2 ]的二氯甲烷溶液中（M = Rh， Ir，cod =环辛-1,5-二烯）得到二硫醇盐桥联的配合物[{Rh 2（μ- biphes）（cod）2 } n ]（n = 2 5或n = 1 6）和[{Ir 2（μ- biphes）（cod）2 } n ]· n CH 2 Cl 2 7。当1,1'-联萘-2,2'-二硫醇（H2个BINAS）与[{的Ir（μ -OMe）（COD）} 2 ]，配合物[Ir 2（μ -binas（COD））2 ] 8获得。配合物5和6与一氧化碳反应，得到二核四羰基配合物[Rh 2（μ- biphes）（CO）4 ] 9。9与PR 3的反应提供了混合配体络合物[{Rh 2（μ- biphes）（CO）2（PR 3）2 } 2 ]· xCH 2 Cl

  DOI：

  10.1016/s0022-328x(97)00151-4
• 作为产物：
  描述：

  (R)-(+)-4,4'-biphenanthryl-3,3'-diyl-S,S-bis-N,N-dimethyl carbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到2-(4-丁一氧代丁氧基)乙醇
  参考文献：
  名称：

  Synthesis of Structurally Modified Atropisomeric Biaryl Dithiols. Observations on the Newman-Kwart Rearrangement

  摘要：

  The preparation of a number of biaryldithiols from biaryldiols is discussed. A key reaction is the Newman-Kwart thermorearrangement of bisthiocarbamates and crucial variables of temperature and reaction time have been identified. Alternative approaches to 3,3'-disubstituted dithiols via ortho metallation are presented, The benefit of using such disubstituted compounds is illustrated with representative examples of the stereochemical features of the derived carbanions in reactions with prochiral electrophiles. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00268-8

文献信息

• New axially chiral sulfur compounds: Synthesis and conformational stability of enantiopure 4,4′-biphenanthrene-3,3′-dithiol and related atropisomeric derivatives
  作者：Antonio Dore、Davide Fabbri、Serafino Gladiali、Giovanni Valle

  DOI：10.1016/0957-4166(95)00074-y

  日期：1995.3

  Enantiopure (R)- and (S)-4,4'-biphenanthrene-3,3'-dithiol la has been prepared for the first time through a synthetic procedure involving in the key step a stereoconservative Newman-Kwart thermorearrangement of the bis-N,N-dimethylthiocarbamoyl ester of(R)- and (S)-biphenanthrol 2b, respectively. The atropisomeric conformations of la are not interconverted even at temperatures as high as 285 degrees C, whereas the related biphenanthrothiophene 3 is completely racemized in a few minutes at 250 degrees C. The axially chiral backbone of la has been incorporated in a set of novel C-2 symmetry sulfur reagents suitable for a variety of stereoselective reactions.
• Metal complexes with atropisomeric sulfur ligands in asymmetric hydroformylation X-ray structure of [Rh2(μ-biphes)(cod)2] (H2biphes = 4,4′-biphenanthrene-3,3′-dithiol)
  作者：Nuria Ruiz、Abdellatif Aaliti、Jorge Forniés-Cámer、Aurora Ruiz、Carmen Claver、Christine J. Cardin、Davide Fabbri、Serafino Gladiali

  DOI：10.1016/s0022-328x(97)00151-4

  日期：1997.1

  The addition of the atropisomeric racemic sulfur compound 4,4′-biphenanthrene-3,3′-dithiol (H2 biphes) to a dichloromethane solution of [M(μ-OMe)(cod)}2] (M = Rh, Ir, cod = cycloocta-1,5-diene) afforded the dithiolate-bridged complexes [Rh2(μ-biphes)(cod)2}n] (n = 2 5 or n = 1 6) and [Ir2(μ-biphes)(cod)2}n]·nCH2Cl27. When 1,1′-binaphthalene-2,2′-dithiol (H2 binas) reacted with [Ir(μ-OMe)(cod)}2]

  将阻转异构的外消旋硫化合物4,4'-联菲-3,3'-二硫醇（H 2 biphes）添加到[M（μ- OMe）（cod）} 2 ]的二氯甲烷溶液中（M = Rh， Ir，cod =环辛-1,5-二烯）得到二硫醇盐桥联的配合物[Rh 2（μ- biphes）（cod）2 } n ]（n = 2 5或n = 1 6）和[Ir 2（μ- biphes）（cod）2 } n ]· n CH 2 Cl 2 7。当1,1'-联萘-2,2'-二硫醇（H2个BINAS）与[的Ir（μ -OMe）（COD）} 2 ]，配合物[Ir 2（μ -binas（COD））2 ] 8获得。配合物5和6与一氧化碳反应，得到二核四羰基配合物[Rh 2（μ- biphes）（CO）4 ] 9。9与PR 3的反应提供了混合配体络合物[Rh 2（μ- biphes）（CO）2（PR 3）2 } 2 ]· xCH 2 Cl
• Synthesis of Structurally Modified Atropisomeric Biaryl Dithiols. Observations on the Newman-Kwart Rearrangement
  作者：Sergio Cossu、Ottorino De Lucchi、Davide Fabbri、Giovanni Valle、Gavin F. Painter、Robin A.J. Smith

  DOI：10.1016/s0040-4020(97)00268-8

  日期：1997.4

  The preparation of a number of biaryldithiols from biaryldiols is discussed. A key reaction is the Newman-Kwart thermorearrangement of bisthiocarbamates and crucial variables of temperature and reaction time have been identified. Alternative approaches to 3,3'-disubstituted dithiols via ortho metallation are presented, The benefit of using such disubstituted compounds is illustrated with representative examples of the stereochemical features of the derived carbanions in reactions with prochiral electrophiles. (C) 1997 Published by Elsevier Science Ltd.