1,2-diselenolan-4-ol | 181052-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-diselenolan-4-ol
• 英文别名: 4-Hydroxy-1,2-diselenolane；diselenolan-4-ol
• CAS: 181052-20-0
• 化学式: C₃H₆OSe₂
• 分子量: 216.0
• InChiKey: UAIHNMIQHFCLGA-UHFFFAOYSA-N

物化性质

• 沸点：
  299.3±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-diselenolan-4-ol 、 camptothecin C20-chloroformate 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 CPT-Se3
  参考文献：
  名称：

  Integration of a Diselenide Unit Generates Fluorogenic Camptothecin Prodrugs with Improved Cytotoxicity to Cancer Cells

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c01362
• 作为产物：
  描述：

  在 邻二甲苯 、 丙酮 作用下， 反应 1.0h， 以5%的产率得到1,2-diselenolan-4-ol
  参考文献：
  名称：

  Reactions of chloromethyloxirane and dihalopropanols with chalcogens in basic reducing systems

  摘要：

  Chloromethyloxirane and 2,3-dibromopropan-l-ol reacted with a solution of selenium or tellurium in the system hydrazin hydrate-potassium hydroxide (K2Se2, K2Te2) to give allyl alcohol; the reaction was accompanied by regeneration of the initial free chalcogen. 1,3-Dichloropropan-2-ol reacted with selenium in the same system to give oligomeric product having a 2-hydroxypropane-1,3-diyidiseleno monomeric unit, while the reaction with tellurium led to the formation of allyl alcohol and almost complete regeneration of initial tellurium. Probable reaction mechanisms are discussed. Polyselenide oligomers containing a hydroxy group in a monomeric unit were formed in reactions of chloromethyloxirane and 1,3-dichloropropan-2-ol with selenium in the system hydrazine hydrate-2-aininoethanol. Under analogous conditions 2,3-dibromopropan-l-ol was converted into allyl alcohol with regeneration of elemental selenium. Reductive cleavage of poly-selenide oligomers gave Se-methyl derivatives of 2-hydroxypropane-1,3-diselenol.

  DOI：

  10.1134/s1070428008040064

文献信息

• Combination of chemotherapy and oxidative stress to enhance cancer cell apoptosis
  作者：Xinming Li、Yanan Hou、Jintao Zhao、Jin Li、Song Wang、Jianguo Fang

  DOI：10.1039/c9sc05997k

  日期：——

  The 1,2-diselenolane unit is a general scaffold to construct glutathione-dependent prodrugs that show increased potency to cancer cells, and workviaa combination of chemotherapy and oxidative stress.

  1,2-二硒环戊烷单元是构建依赖谷胱甘肽的前药的通用支架，表现出对癌细胞增强的效力，并通过化疗和氧化应激的组合发挥作用。
• Selenoacetalyzation of 4-Formylpyrazoles in the Presence of Trimethylchlorosilane
  作者：Lyubov K. Papernaya、Alexandra A. Shatrova、Ekaterina P. Levanova、Alexandr I. Albanov、Lyudmila V. Klyba、Elena V. Rudyakova、Galina G. Levkovskaya

  DOI：10.1002/hc.21113

  日期：2013.11

  The reaction of 3,5-dimethyl-4-formylpyrazoles, bearing various substituents at N-1 atom, with propane-1,3-diselenol and 2-hydroxypropane-1,3-diselenol in the presence of ТМSCl proceeds without heating to chemoselectively give hitherto unknown 2-(pyrazol-4-yl)-1,3-diselenane hydrochlorides in high yields. The latter are easily transformed to the corresponding free bases—2-(pyrazol-4-yl)-1,3-diselenanes

  在 ТМSCl 存在下，在 N-1 原子上带有各种取代基的 3,5-二甲基-4-甲酰基吡唑与丙烷-1,3-二硒醇和 2-羟基丙烷-1,3-二硒醇的反应无需加热即可进行化学选择性以高收率得到迄今未知的 2-(pyrazol-4-yl)-1,3-二硒烷盐酸盐。后者很容易转化为相应的游离碱 - 2-（吡唑-4-基）-1,3-二硒烷。通过 2D HMBC-gp (15N-1H) 技术获得的 2-(pyrazol-4-yl)-1,3-二硒烷中吡唑环的 15N 化学位移表明盐酸盐中的 N-2 原子质子化。
• Integration of a Diselenide Unit Generates Fluorogenic Camptothecin Prodrugs with Improved Cytotoxicity to Cancer Cells
  作者：Jintao Zhao、Zihua Wang、Miao Zhong、Qianhe Xu、Xinming Li、Bingbing Chang、Jianguo Fang

  DOI：10.1021/acs.jmedchem.1c01362

  日期：2021.12.23
• Reactions of chloromethyloxirane and dihalopropanols with chalcogens in basic reducing systems
  作者：A. V. Elaev、V. A. Grabel’nykh、N. V. Russavskaya、E. P. Levanova、E. N. Sukhomazova、E. R. Zhanchipova、L. V. Klyba、A. I. Albanov、N. A. Korchevin

  DOI：10.1134/s1070428008040064

  日期：2008.4

  Chloromethyloxirane and 2,3-dibromopropan-l-ol reacted with a solution of selenium or tellurium in the system hydrazin hydrate-potassium hydroxide (K2Se2, K2Te2) to give allyl alcohol; the reaction was accompanied by regeneration of the initial free chalcogen. 1,3-Dichloropropan-2-ol reacted with selenium in the same system to give oligomeric product having a 2-hydroxypropane-1,3-diyidiseleno monomeric unit, while the reaction with tellurium led to the formation of allyl alcohol and almost complete regeneration of initial tellurium. Probable reaction mechanisms are discussed. Polyselenide oligomers containing a hydroxy group in a monomeric unit were formed in reactions of chloromethyloxirane and 1,3-dichloropropan-2-ol with selenium in the system hydrazine hydrate-2-aininoethanol. Under analogous conditions 2,3-dibromopropan-l-ol was converted into allyl alcohol with regeneration of elemental selenium. Reductive cleavage of poly-selenide oligomers gave Se-methyl derivatives of 2-hydroxypropane-1,3-diselenol.