2-Acetoxy-1-methoxy-3,4-bis(thioacetoxy)-5-<2-(N-acetylamino)ethyl>benzene | 133883-07-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Acetoxy-1-methoxy-3,4-bis(thioacetoxy)-5-<2-(N-acetylamino)ethyl>benzene
• 英文别名: 3-methoxy-4-acetoxy-5,6-diacetylthio-N-acetylphenylethylamine；tetraacetyl lissoclinotoxin A；[4-(2-Acetamidoethyl)-2,3-bis(acetylsulfanyl)-6-methoxyphenyl] acetate
• CAS: 133883-07-5
• 化学式: C₁₇H₂₁NO₆S₂
• 分子量: 399.489
• InChiKey: YPSGCXYZQSTOBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3-dibutylthio-4-(2-nitroethylene)-phenol 在 吡啶 、 lithium aluminium tetrahydride 、 sodium 作用下， 以 乙醚 为溶剂， 反应 23.0h， 生成 2-Acetoxy-1-methoxy-3,4-bis(thioacetoxy)-5-<2-(N-acetylamino)ethyl>benzene
  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.
• Lissoclinotoxin A, an antibiotic 1,2,3-trithiane derivative from the tunicate Lissoclinum perforatum.
  作者：Marc Litaudon、Michèle Guyot

  DOI：10.1016/s0040-4039(00)92118-x

  日期：1991.2

  Lissoclinotoxin A, a new antibiotic 1,2,3-trithiane derivative, was isolated from the Tunicate Lissoclinum perforatum. The structure elucidation was based upon spectral data.