4-chloromethyl-7,8-diacetoxy<1>benzopyran-2(H)-one | 121565-43-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-chloromethyl-7,8-diacetoxy<1>benzopyran-2(H)-one
• 英文别名: 7,8-diacetoxy-4-chloromethyl-2-oxo-2H-1-benzopyran；[8-Acetyloxy-4-(chloromethyl)-2-oxochromen-7-yl] acetate
• CAS: 121565-43-3
• 化学式: C₁₄H₁₁ClO₆
• 分子量: 310.691
• InChiKey: HHXJHVURFLTSLI-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  477.2±45.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-chloromethyl-7,8-diacetoxy<1>benzopyran-2(H)-one 在 甲醇 、 四丁基溴化铵 、 锌 作用下， 以 乙酸酐 为溶剂， 生成 4-(α-acetoxymethyl)-7,8-dihydroxy<1>benzopyran-2(H)-one
  参考文献：
  名称：

  Singh, R. P.; Singh, R. V.; Malik, O. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1031

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯三酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 四丁基溴化铵 作用下， 生成 4-chloromethyl-7,8-diacetoxy<1>benzopyran-2(H)-one
  参考文献：
  名称：

  Singh, R. P.; Singh, R. V.; Malik, O. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1031

  摘要：

  DOI：

文献信息

• An efficient ZrCl4 catalyzed one-pot solvent free protocol for the synthesis of 4-substituted coumarins
  作者：G.V.M. Sharma、J. Janardhan Reddy、P. Sree Lakshmi、P. Radha Krishna

  DOI：10.1016/j.tetlet.2005.06.166

  日期：2005.9

  A versatile and efficient route to 4-substituted cournarins via a Pechmann reaction using ZrCl4 as the catalyst (10 mol %) is described. This method provides several advantages over alternative procedures such as mild, solvent-free conditions at ambient temperature, and direct isolation of the products in high yields. (c) 2005 Published by Elsevier Ltd.
• Synthesis and protective effects of coumarin derivatives against oxidative stress induced by doxorubicin
  作者：Adeline Beillerot、Juan-Carlos Rodríguez Domínguez、Gilbert Kirsch、Denyse Bagrel

  DOI：10.1016/j.bmcl.2007.12.004

  日期：2008.2

  The use of doxorubicin (DOX) in the treatment of solid tumors is limited by cardiotoxicity essentially due to oxidative stress generation. The aim of this study was to identify coumarin derivatives displaying a protective antioxidant activity without affecting DOX antitumoral efficiency. A set of eighteen coumarinic derivatives was synthesized. Their antioxidant power was evaluated in vitro with the FRAP (ferric reducing ability of plasma) method and in human breast adenocarcinoma MCF7 cells using H,DCFDA (2',7'-dichlorodihydrofluorescein diacetate) in a cytometric analysis. 4-Methyl-7,8-dihydroxycoumarin was found to exhibit an important antioxidant strength, a low cytotoxicity, and could decrease ROS (reactive oxygen species) production generated by DOX treatment without affecting DOX cytotoxicity in MCF7 cells. (C) 2007 Elsevier Ltd. All rights reserved.
• SINGH, R. P.;SINGH, R. V.;MALIK, O. P., INDIAN J. CHEM. B, 27,(1988) N1, C. 1031
  作者：SINGH, R. P.、SINGH, R. V.、MALIK, O. P.

  DOI：——

  日期：——