二碘乙酸甲酯 | 960048-89-9

• 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
• 中文名称: 二碘乙酸甲酯
• 英文名称: methyl 2,2-diiodoacetate
• 英文别名: Methyldiiodacetat；diiodo-acetic acid methyl ester；Dijod-essigsaeure-methylester
• CAS: 960048-89-9
• 化学式: C₃H₄I₂O₂
• 分子量: 325.873
• InChiKey: RZSPUYZPOKSISN-UHFFFAOYSA-N

物化性质

• 沸点：
  251.0±20.0 °C(Predicted)
• 密度：
  2.725±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二碘乙酸甲酯 在 ammonium hydroxide 作用下， 生成 二碘乙酰胺
  参考文献：
  名称：

  Occurrence, Synthesis, and Mammalian Cell Cytotoxicity and Genotoxicity of Haloacetamides: An Emerging Class of Nitrogenous Drinking Water Disinfection Byproducts

  摘要：

  The haloacetamides, a class of emerging nitrogenous drinking water disinfection byproduct (DBPs), were analyzed for their chronic cytotoxicity and for the induction of genomic DNA damage in Chinese hamster ovary cells. The rank order for cytotoxicity of 13 haloacetamides was DIAcAm > IAcAm > BAcAm > TBAcAm > BIAcAm > DBCAcAm > CIAcAm > BDCAcAm > DBAcAm > BCAcAm > CAcAm > DCAcAm > TCAcAm. The rank order of their genotoxicity was TBAcAm > DIAcAm IAcAm > BAcAm > DBCAcAm > BIAcAm > BDCAcAm > CIAcAm > BCAcAm > DBAcAm > CAcAm > TCAcAm. DCAcAm was not genotoxic. Cytotoxicity and genotoxicity were primarily determined by the leaving tendency of the halogens and followed the order I > Br > > CI. With the exception of brominated trihaloacetamides, most of the toxicity rank order was consistent with structure-activity relationship expectations. For di- and trihaloacetamides, the presence of at least one good leaving halogen group (I or Br but not CI) appears to be critical for significant toxic activity. Log P was not a factor for monohaloacetamides but may play a role in the genotoxicity of trihaloacetamides and possible activation of dihaloacetamides by intracellular GSH and -SH compounds. With the advent of the U.S. EPA Stage 2 DBP regulations, water utilities are considering the use of disinfectants that are alternatives to chlorine. The use of these alternative disinfectants will shift the distribution of DBP chemical classes. The emergence of new, highly toxic iodinated, nitrogenous DBPs, as illustrated by the discovery of bromoiodoacetamide as a new DBP, underscores the importance of comparative toxicity studies to assist in the overall goal of safer drinking water practice.

  DOI：

  10.1021/es071754h
• 作为产物：
  描述：

  重氮乙酸甲酯 在 碘 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到二碘乙酸甲酯
  参考文献：
  名称：

  第二代全合成（–）-前异色酮D

  摘要：

  达到了立体选择性，高收率的甲基甲硅烷基乙烯酮缩醛在多克级的基于苯醌的底物上的添加。引入的共轭物加成缩短了（-）-前异色酮D的总合成，并为进一步研究前异色酮E和F的总合成奠定了坚实的基础。

  DOI：

  10.1002/ejoc.202000465

文献信息

• Willstaetter, Chemische Berichte, 1902, vol. 35, p. 1385
  作者：Willstaetter

  DOI：——

  日期：——
• Second Generation Total Synthesis of (–)‐Preussochromone D
  作者：Eric Kerste、Marc Paul Beller、Ulrich Koert

  DOI：10.1002/ejoc.202000465

  日期：2020.6.30

  acetals to chromenone‐based substrates on multigram‐scale has been achieved. The introduced conjugate addition shortens the total synthesis of (–)‐preussochromone D and establishes a robust entry for further investigations towards the total synthesis of preussochromone E and F.

  达到了立体选择性，高收率的甲基甲硅烷基乙烯酮缩醛在多克级的基于苯醌的底物上的添加。引入的共轭物加成缩短了（-）-前异色酮D的总合成，并为进一步研究前异色酮E和F的总合成奠定了坚实的基础。
• Occurrence, Synthesis, and Mammalian Cell Cytotoxicity and Genotoxicity of Haloacetamides: An Emerging Class of Nitrogenous Drinking Water Disinfection Byproducts
  作者：Michael J. Plewa、Mark G. Muellner、Susan D. Richardson、Francesca Fasano、Katherine M. Buettner、Yin-Tak Woo、A. Bruce McKague、Elizabeth D. Wagner

  DOI：10.1021/es071754h

  日期：2008.2.1

  The haloacetamides, a class of emerging nitrogenous drinking water disinfection byproduct (DBPs), were analyzed for their chronic cytotoxicity and for the induction of genomic DNA damage in Chinese hamster ovary cells. The rank order for cytotoxicity of 13 haloacetamides was DIAcAm > IAcAm > BAcAm > TBAcAm > BIAcAm > DBCAcAm > CIAcAm > BDCAcAm > DBAcAm > BCAcAm > CAcAm > DCAcAm > TCAcAm. The rank order of their genotoxicity was TBAcAm > DIAcAm IAcAm > BAcAm > DBCAcAm > BIAcAm > BDCAcAm > CIAcAm > BCAcAm > DBAcAm > CAcAm > TCAcAm. DCAcAm was not genotoxic. Cytotoxicity and genotoxicity were primarily determined by the leaving tendency of the halogens and followed the order I > Br > > CI. With the exception of brominated trihaloacetamides, most of the toxicity rank order was consistent with structure-activity relationship expectations. For di- and trihaloacetamides, the presence of at least one good leaving halogen group (I or Br but not CI) appears to be critical for significant toxic activity. Log P was not a factor for monohaloacetamides but may play a role in the genotoxicity of trihaloacetamides and possible activation of dihaloacetamides by intracellular GSH and -SH compounds. With the advent of the U.S. EPA Stage 2 DBP regulations, water utilities are considering the use of disinfectants that are alternatives to chlorine. The use of these alternative disinfectants will shift the distribution of DBP chemical classes. The emergence of new, highly toxic iodinated, nitrogenous DBPs, as illustrated by the discovery of bromoiodoacetamide as a new DBP, underscores the importance of comparative toxicity studies to assist in the overall goal of safer drinking water practice.