(trifluoroacetyl)glycolyl chloride | 78517-62-1

• 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: (trifluoroacetyl)glycolyl chloride
• 英文别名: (2-Chloro-2-oxoethyl) 2,2,2-trifluoroacetate；(2-chloro-2-oxoethyl) 2,2,2-trifluoroacetate
• CAS: 78517-62-1
• 化学式: C₄H₂ClF₃O₃
• 分子量: 190.506
• InChiKey: OEYDNZNYCQJMHH-UHFFFAOYSA-N

物化性质

• 沸点：
  139.4±40.0 °C(Predicted)
• 密度：
  1.549±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  脱羰秋水仙碱 、 (trifluoroacetyl)glycolyl chloride 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以540 mg的产率得到N-(hydroxyacetyl)demecolcine
  参考文献：
  名称：

  Biological effects of modified colchicines. 2. Evaluation of catecholic colchicines, colchifolines, colchicide, and novel N-acyl- and N-aroyldeacetylcolchicines

  摘要：

  A series of natural and synthetic colchicine derivatives was examined for their potency in the lymphocytic leukemia P388 screen in mice, for their toxicity in mice, and for their binding to microtubule protein. The natural alkaloids cornigerine and colchifoline and several N,O-substituted analogues of colchifoline were found to be as potent and as toxic as colchicine in the P388 screen with good affinity for tubulin. The 1,2-(methylenedioxy)-substituted isomer of cornigerine was considerably less potent in vivo than could have been anticipated from the in vitro tubulin binding data. Several N-acyl and N-aroyl derivatives prepared from deacetylcolchicine showed high potency in the in vitro and in vivo screens. Colchicide was found to be highly potent in vivo, and N-carbethoxydeacetylcolchicine, a synthetic analogue of colchicine with a N-carbethoxy instead of an N-acetyl function, showed interesting biological properties.

  DOI：

  10.1021/jm00364a006
• 作为产物：
  描述：

  (2,2,2-三氟乙酰氧基)乙酸 在 氯化亚砜 作用下， 反应 6.0h， 以78%的产率得到(trifluoroacetyl)glycolyl chloride
  参考文献：
  名称：

  Iorio, Maria A.; Molinari, Marisa; Brossi, Arnold, Canadian Journal of Chemistry, 1981, vol. 59, p. 283 - 284

  摘要：

  DOI：

文献信息

• Biological effects of modified colchicines. 2. Evaluation of catecholic colchicines, colchifolines, colchicide, and novel N-acyl- and N-aroyldeacetylcolchicines
  作者：Arnold Brossi、Padam N. Sharma、Louise Atwell、Arthur E. Jacobson、Maria A. Iorio、Marisa Molinari、Colin F. Chignell

  DOI：10.1021/jm00364a006

  日期：1983.10

  A series of natural and synthetic colchicine derivatives was examined for their potency in the lymphocytic leukemia P388 screen in mice, for their toxicity in mice, and for their binding to microtubule protein. The natural alkaloids cornigerine and colchifoline and several N,O-substituted analogues of colchifoline were found to be as potent and as toxic as colchicine in the P388 screen with good affinity for tubulin. The 1,2-(methylenedioxy)-substituted isomer of cornigerine was considerably less potent in vivo than could have been anticipated from the in vitro tubulin binding data. Several N-acyl and N-aroyl derivatives prepared from deacetylcolchicine showed high potency in the in vitro and in vivo screens. Colchicide was found to be highly potent in vivo, and N-carbethoxydeacetylcolchicine, a synthetic analogue of colchicine with a N-carbethoxy instead of an N-acetyl function, showed interesting biological properties.
• Iorio, Maria A.; Molinari, Marisa; Brossi, Arnold, Canadian Journal of Chemistry, 1981, vol. 59, p. 283 - 284
  作者：Iorio, Maria A.、Molinari, Marisa、Brossi, Arnold

  DOI：——

  日期：——