2,3-bis(n-butylthio)-4-hydroxy-5-methoxybenzaldehyde | 157458-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3-bis(n-butylthio)-4-hydroxy-5-methoxybenzaldehyde
• 英文别名: 2,3-dibutylthio-4-hydroxy-5-methoxybenzaldehyde；2,3-Bis(butylsulfanyl)-4-hydroxy-5-methoxybenzaldehyde
• CAS: 157458-10-1
• 化学式: C₁₆H₂₄O₃S₂
• 分子量: 328.497
• InChiKey: MDTFEHPECAYWRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  426.7±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-bis(n-butylthio)-4-hydroxy-5-methoxybenzaldehyde 在 lithium aluminium tetrahydride 、 TEA 、 ammonium acetate 、 氨 、 四丁基碘化铵 、 lithium 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 水 、 溶剂黄146 为溶剂， 反应 12.5h， 生成 N-(Boc)-2',3'-dimercapto-4',5'-dimethoxyphenethylamine
  参考文献：
  名称：

  Acid-Promoted DNA-Cleaving Activities and Total Synthesis of Varacin C

  摘要：

  The first total synthesis of the antibiotic varacin C has been accomplished. In addition, it has been demonstrated that this antibiotic exhibits potent antitumor activity and is capable of causing efficient DNA cleavage under acidic conditions.

  DOI：

  10.1021/ja020531i
• 作为产物：
  描述：

  2,3-二溴-4-羟基-5-甲氧基苯甲醛 、 N-丁基硫醇铜 以 吡啶 、 喹啉 为溶剂， 反应 1.0h， 以38%的产率得到2,3-bis(n-butylthio)-4-hydroxy-5-methoxybenzaldehyde
  参考文献：
  名称：

  Lissoclinotoxins: Antibiotic polysulfur derivatives from the tunicate Lissoclinum perforatum. Revised structure of lissoclinotoxin A

  摘要：

  Lissoclinotoxin B, a new pentathiepin derivative, was isolated from the tonicate Lissoclinum perforatum. Structure elucidation of this compound is described based on spectroscopic data, together with a revised structure for lissoclinotoxin A. A synthesis of tetraacetyl isolissoclinotoxin A is described.

  DOI：

  10.1016/s0040-4020(01)80690-6

文献信息

• Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A
  作者：Paul W. Ford、Mathew R. Narbut、Jack Belli、Bradley S. Davidson

  DOI：10.1021/jo00099a026

  日期：1994.10

  The unique pentathiepin-containing compounds varacin (1) and isolissoclinotoxin A (3) have each been synthesized in eight steps from vanillin. Formation of the pentathiepin ring in varacin was accomplished by treatment of the dithiolate anion, generated from the Na/NH3 reduction of bisbutyl sulfide intermediate 10, with 2 equiv of S2Cl2. Placement of the sulfur atoms on the aromatic ring was accomplished by treatment of 5,6-dibromovanillin (6) with cuprous n-butylmercaptide in pyridine/quinoline at 160 degrees C. The structure of the penultimate intermediate, TEOC-protected varacin (II), was confirmed by X-ray diffraction analysis. Isolissoclinotoxin A was prepared in an analogous manner, using a MOM group to protect the phenol. The structure of varacin has been confirmed; however, reductive acetylation of 3 yielded tetraacetate derivative 20, which was different than that reported as a product of lissoclinotoxin A acetylation. Because the data recorded for 20 did not match that previously reported, it is likely that the structure of lissoclinotoxin A should be reassigned to regioisomer 4, which has the phenol and methoxy group interchanged.
• Lissoclinotoxins: Antibiotic polysulfur derivatives from the tunicate Lissoclinum perforatum. Revised structure of lissoclinotoxin A
  作者：Marc Litaudon、François Trigalo、Marie-Thérése Martin、François Frappier、Michéle Guyot

  DOI：10.1016/s0040-4020(01)80690-6

  日期：1994.5

  Lissoclinotoxin B, a new pentathiepin derivative, was isolated from the tonicate Lissoclinum perforatum. Structure elucidation of this compound is described based on spectroscopic data, together with a revised structure for lissoclinotoxin A. A synthesis of tetraacetyl isolissoclinotoxin A is described.
• Acid-Promoted DNA-Cleaving Activities and Total Synthesis of Varacin C
  作者：Alex H. F. Lee、Jian Chen、Dongsheng Liu、Thomas Y. C. Leung、Albert S. C. Chan、Tianhu Li

  DOI：10.1021/ja020531i

  日期：2002.11.1

  The first total synthesis of the antibiotic varacin C has been accomplished. In addition, it has been demonstrated that this antibiotic exhibits potent antitumor activity and is capable of causing efficient DNA cleavage under acidic conditions.