5-(2-phenyl-1,3,2-dithiarsinan-4-yl)pentanoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(2-phenyl-1,3,2-dithiarsinan-4-yl)pentanoic acid
• 英文别名: 5-(2-Phenyl-1,3,2-dithiarsinan-4-yl)pentanoic acid
• 化学式: C₁₄H₁₉AsO₂S₂
• 分子量: 358.357
• InChiKey: BSZVDLMKZQJUKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-二氢硫辛酸 以 四氢呋喃 为溶剂， 反应 27.5h， 生成 5-(2-phenyl-1,3,2-dithiarsinan-4-yl)pentanoic acid
  参考文献：
  名称：

  Models for the Inhibition of Dithiol‐Containing Enzymes by Organoarsenic Compounds: Synthetic Routes and the Structure of [PhAs(HlipS ₂ )] (HlipS ₂ ²⁻ = Reduced Lipoic Acid)

  摘要：

  DOI：

  10.1002/(sici)1099-0682(199801)1998:1<61::aid-ejic61>3.0.co;2-#

文献信息

• Thiolates of arsenic(III), antimony(III), and bismuth(III) with dl-α-dihydrolipoic acid
  作者：Panayiotis V. Ioannou、Gerasimos M. Tsivgoulis

  DOI：10.1007/s00706-014-1186-9

  日期：2014.6

  Lipoic acid can be reduced to dihydrolipoic acid free of lipoic acid without using deoxygenated solvents. Dihydrolipoic acid reacted with phenylarsine oxide, As2O3, and AsCl3, SbCl3 but not Sb2O3, and Bi2O3, BiCl3, and Bi(NO3)(3)center dot 5H(2)O in various solvents giving thiolates. When the reactions were done in methanol, the HCl and HNO3 released caused esterification of the -COOH group. The reaction with As(III) compounds was sensitive to dioxygen, leading to production of lipoic acid derivatives as well, arsenite being particularly active for the autoxidation. Physical (H-1 NMR) and chemical [reactivity of >M-Cl and >Bi(NO3)] properties of the adducts are described. The six-membered dihydrolipoic acid complexes reacted with stoichiometric amounts of British Anti-Lewisite releasing the dihydrolipoic acid by forming the corresponding complexes of British Anti-Lewisite.
• Models for the Inhibition of Dithiol‐Containing Enzymes by Organoarsenic Compounds: Synthetic Routes and the Structure of [PhAs(HlipS ₂ )] (HlipS ₂ ²⁻ = Reduced Lipoic Acid)
  作者：Angelika von Döllen、Henry Strasdeit

  DOI：10.1002/(sici)1099-0682(199801)1998:1<61::aid-ejic61>3.0.co;2-#

  日期：1998.1