3,3'-二甲基-1,1'-联萘-2,2'-二硫醇 | 190841-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3,3'-二甲基-1,1'-联萘-2,2'-二硫醇
• 英文名称: 3,3'-Dimethyl-[1,1']binaphthalenyl-2,2'-dithiol
• 英文别名: 3,3'-Dimethyl[1,1'-binaphthalene]-2,2'-dithiol；3-methyl-1-(3-methyl-2-sulfanylnaphthalen-1-yl)naphthalene-2-thiol
• CAS: 190841-68-0
• 化学式: C₂₂H₁₈S₂
• 分子量: 346.517
• InChiKey: YLWGGSVDHYBPKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  3,3'-二甲基-1,1'-联萘-2,2'-二硫醇 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (S)-(2,6-Dimethyl-3,5-dithia-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-phenyl-methanol
  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
• 作为产物：
  描述：

  3-(4-羟基苯基)苯甲基醇 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到3,3'-二甲基-1,1'-联萘-2,2'-二硫醇
  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

• 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.