4,4'-dithiobis(3-nitrobenzyl alcohol) | 35350-36-8

• 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: 4,4'-dithiobis(3-nitrobenzyl alcohol)
• 英文别名: [4-[[4-(Hydroxymethyl)-2-nitrophenyl]disulfanyl]-3-nitrophenyl]methanol；[4-[[4-(hydroxymethyl)-2-nitrophenyl]disulfanyl]-3-nitrophenyl]methanol
• CAS: 35350-36-8
• 化学式: C₁₄H₁₂N₂O₆S₂
• 分子量: 368.391
• InChiKey: XNRPYEKKMYEEPG-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  604.7±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  183
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3-二氯吡嗪 、 4-氯-3-硝基苯甲醇 在 sodium sulfide 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 5.0h， 以10%的产率得到4,4'-dithiobis(3-nitrobenzyl alcohol)
  参考文献：
  名称：

  Practical Syntheses of the Adhesion Molecule Inhibitor ER-49890 and Its Stereoisomer

  摘要：

  Practical synthetic routes to anti-[3-(10H-pyrazino[2,3 -b] [ 1,4]-benzothiazin-8 -ylmethyl)-3 -azabicyclo [3.3.1]non-9-yl]acetic acid (ER-49890, 1) and its syn-isomer are reported. The anti-(3-azabicyclo[3.3.1]non-9-yl)acetic acid side chain (anti-12) was synthesized stereoselectively using Pd/C hydrogenation in the presence of HCL The syn-isomer (syn-12) was concisely obtained by crystallization as its oxalic acid salt from a 1: 1 mixture of anti- and syn-isomers. The 10H-pyrazino[2,3-b][1,4]benzothiazine core (7) was prepared from commercially available 4-chloro-3-nitrobenzyl alcohol (13) in four steps and good yield.

  DOI：

  10.3987/com-04-10279

文献信息

• Practical Syntheses of the Adhesion Molecule Inhibitor ER-49890 and Its Stereoisomer
  作者：Toshihiko Kaneko、Fumihiro Ozaki、Richard S. J. Clark、Yuki Komatsu、Kazuo Okano

  DOI：10.3987/com-04-10279

  日期：——

  Practical synthetic routes to anti-[3-(10H-pyrazino[2,3 -b] [ 1,4]-benzothiazin-8 -ylmethyl)-3 -azabicyclo [3.3.1]non-9-yl]acetic acid (ER-49890, 1) and its syn-isomer are reported. The anti-(3-azabicyclo[3.3.1]non-9-yl)acetic acid side chain (anti-12) was synthesized stereoselectively using Pd/C hydrogenation in the presence of HCL The syn-isomer (syn-12) was concisely obtained by crystallization as its oxalic acid salt from a 1: 1 mixture of anti- and syn-isomers. The 10H-pyrazino[2,3-b][1,4]benzothiazine core (7) was prepared from commercially available 4-chloro-3-nitrobenzyl alcohol (13) in four steps and good yield.