2-methyl-3-(1-thiooctyl)-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-3-(1-thiooctyl)-1,4-naphthoquinone
• 英文别名: 2-methyl-3-octylmercapto-[1,4]naphthoquinone；2-Methyl-3-octylmercapto-[1,4]naphthochinon；2-Methyl-3-(octylsulfanyl)naphthalene-1,4-dione；2-methyl-3-octylsulfanylnaphthalene-1,4-dione
• 化学式: C₁₉H₂₄O₂S
• mdl: MFCD12035412
• 分子量: 316.464
• InChiKey: SAXFHZWUVDPCCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(1-thiooctyl)-1,4-naphthoquinone 在 双氧水 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以61%的产率得到2,3-epoxy-2-methyl-3-(1-thiooctyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Thioalkyl Derivatives of Vitamin K3 and Vitamin K3 Oxide Inhibit Growth of Hep3B and HepG2 Cells

  摘要：

  A new hypothesis regarding the effect of vitamin K-3 On hepatoma cell growth is presented. In brief, exploration of cell growth activity has been identified with the action of p34(cdc2) kinase and its associated protein tyrosine phosphatase. After exploring a series of substituted derivatives of vitamin K and vitamin K-3 oxide, we suggest a mechanism involving alkylation at the active-site cysteine for the inhibition of the protein tyrosine phosphatase which controls the activity of the p34(cdc2) kinase. (C) 1995 Academic Press, Inc.

  DOI：

  10.1006/bioo.1995.1008
• 作为产物：
  描述：

  1-辛硫醇 、 甲萘醌 以89%的产率得到2-methyl-3-(1-thiooctyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of sulfur-containing analogs of the K group vitamins by an electrochemical method

  摘要：

  An efficient electrochemical method is proposed for obtaining structural analogues of the K group vitamins (3-alkylthio and 3-arylthio ethers of 2-methyl-1,4-naphthoquninone).

  DOI：

  10.1007/bf00863373

文献信息

• Naphthoquinone Antimalarials. XXIII. Bz-Substituted Derivatives
  作者：Louis F. Fieser、Russell H. Brown

  DOI：10.1021/ja01179a010

  日期：1949.11.19
• Synthesis of sulfur-containing analogs of the K group vitamins by an electrochemical method
  作者：M. E. Niyazymbetov、I. V. Aref'eva、E. I. Zakharova、L. D. Konyushkin、S. M. Alekseev、V. P. Litvinov、R. P. Evstigneeva

  DOI：10.1007/bf00863373

  日期：1992.11

  An efficient electrochemical method is proposed for obtaining structural analogues of the K group vitamins (3-alkylthio and 3-arylthio ethers of 2-methyl-1,4-naphthoquninone).
• Thioalkyl Derivatives of Vitamin K3 and Vitamin K3 Oxide Inhibit Growth of Hep3B and HepG2 Cells
  作者：J. Kerns、S. Naganathan、P. Dowd、F.M. Finn、B. Carr

  DOI：10.1006/bioo.1995.1008

  日期：1995.6

  A new hypothesis regarding the effect of vitamin K-3 On hepatoma cell growth is presented. In brief, exploration of cell growth activity has been identified with the action of p34(cdc2) kinase and its associated protein tyrosine phosphatase. After exploring a series of substituted derivatives of vitamin K and vitamin K-3 oxide, we suggest a mechanism involving alkylation at the active-site cysteine for the inhibition of the protein tyrosine phosphatase which controls the activity of the p34(cdc2) kinase. (C) 1995 Academic Press, Inc.