2-hydroxypropane-1,3-diselenol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxypropane-1,3-diselenol
• 英文别名: 1,3-diselanylpropan-2-ol；1,3-Bis(selanyl)propan-2-ol；1,3-bis(selanyl)propan-2-ol
• 化学式: C₃H₈OSe₂
• 分子量: 218.016
• InChiKey: KYQSMBZJPOASQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.01
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• 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：

  十二羰基三铁 、 2-hydroxypropane-1,3-diselenol 以 甲苯 为溶剂， 以51%的产率得到[(µ-SeCH2)2CH(OH)]Fe2(CO)6
  参考文献：
  名称：

  与某些氢化酶活性位点有关的新型蝴蝶[2Fe2Se]簇复合物的合成，结构和性质的研究

  摘要：

  作为我们对仿生化学和蝶形簇化学的研究的继续，已经制备了令人满意的收率的两个系列的“封闭”和“开放”蝶形[2Fe2Se]簇复合物。因此，治疗的Fe 3（CO）12与（HSeCH 2）2在回流甲苯CHOH给出预期的“封闭”蝴蝶[2Fe2Se]簇配合物[（μ-SECH 2）2 CH（OH）]的Fe 2（CO ）6（甲），而“开放”蝴蝶簇络合物（μ-EtSe）[（μ-SECH 2 CH（OH）（CH 2溴）]的Fe 2（CO）6（乙）出乎意料地具有复杂一起产生一个经由（μ-硒的连续反应2）的Fe 2（CO）6用Et 3 BHLi，接着用（BRCH 2）2 CHOH。其他的“闭合”和“打开”簇络合物1 - 6可以由羟基转化和复合物的CO取代反应制备进一步阿和乙。例如，（i）的反应阿与PPH 3和脱羰剂我3 NO，得到PPH 3单取代配合物[（μ-SECH 2）2 CH（OH）] Fe 2（CO）5（PPh

  DOI：

  10.1021/om900572t
• 作为产物：
  描述：

  1,3-二氯丙醇 在 selenium 、 C.I.酸性橙108 、 肼 、 氢氧化钾 作用下， 以 水 为溶剂， 反应 5.5h， 以78%的产率得到2-hydroxypropane-1,3-diselenol
  参考文献：
  名称：

  Selective synthesis of isomeric dithioglycerols

  摘要：

  Reactions of 2,3-dibromopropan-1-ol and 1,3-dichloropropan-2-ol with elemental sulfur activated in the system hydrazine hydrate-2-aminoethanol at 30-35C gave oligomeric polysulfides which were subjected to reductive cleavage with formation of individual dithioglycerol isomers. Activation of sulfur with the use of alkali gives rise to mixtures of isomeric products.

  DOI：

  10.1134/s1070428008100059

文献信息

• 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。
• Investigations on Synthesis, Structure, and Properties of New Butterfly [2Fe2Se] Cluster Complexes Relevant to Active Sites of Some Hydrogenases
  作者：Li-Cheng Song、Wei Gao、Cui-Ping Feng、De-Fu Wang、Qing-Mei Hu

  DOI：10.1021/om900572t

  日期：2009.10.26

  studies on biomimetic chemistry and butterfly cluster chemistry, two series of “closed” and “open” butterfly [2Fe2Se] cluster complexes have been prepared in satisfactory yields. Thus, treatment of Fe3(CO)12 with (HSeCH2)2CHOH in toluene at reflux gave the expected “closed” butterfly [2Fe2Se] cluster complex [(μ-SeCH2)2CH(OH)]Fe2(CO)6 (A), whereas the “open” butterfly cluster complex (μ-EtSe)[(μ-SeCH2CH(OH)(CH2Br)]Fe2(CO)6

  作为我们对仿生化学和蝶形簇化学的研究的继续，已经制备了令人满意的收率的两个系列的“封闭”和“开放”蝶形[2Fe2Se]簇复合物。因此，治疗的Fe 3（CO）12与（HSeCH 2）2在回流甲苯CHOH给出预期的“封闭”蝴蝶[2Fe2Se]簇配合物[（μ-SECH 2）2 CH（OH）]的Fe 2（CO ）6（甲），而“开放”蝴蝶簇络合物（μ-EtSe）[（μ-SECH 2 CH（OH）（CH 2溴）]的Fe 2（CO）6（乙）出乎意料地具有复杂一起产生一个经由（μ-硒的连续反应2）的Fe 2（CO）6用Et 3 BHLi，接着用（BRCH 2）2 CHOH。其他的“闭合”和“打开”簇络合物1 - 6可以由羟基转化和复合物的CO取代反应制备进一步阿和乙。例如，（i）的反应阿与PPH 3和脱羰剂我3 NO，得到PPH 3单取代配合物[（μ-SECH 2）2 CH（OH）] Fe 2（CO）5（PPh
• Synthesis of previously unknown 3,3′-linearly linked sulfur- and selenium-containing bispyrazoles by reactions of 3-alkenyl-5-chloropyrazoles with bischalcogenols
  作者：E. V. Rudyakova、D. O. Samultsev、E. P. Levanova、G. G. Levkovskaya

  DOI：10.1134/s1070428013050175

  日期：2013.5

  By reactions of 3-alkenyl-5-chloropyrazoles with appropriate dichalcogenols the fi rst specimens were obtained of previously unknown 3,3'-linearly linked bispyrazoles containing in the alkyl chain of the linker two heteroatoms, sulfur or selenium. 3-Vinyl-5-chloropyrazoles react with 1,3-propanedithiol, 2-hydroxy-1,3-propanedithiol, and 2-hydroxy-1,3-propanediselenol under UV irradiation and heating at 60A degrees C over 8 h affording products of the addition against Markovnikoff rule. The radical addition of 1,3-propanedithiol to 3-isopropenyl-5-chloropyrazole required a longer time, 15 h.
• Selective synthesis of isomeric dithioglycerols
  作者：E. P. Levanova、V. A. Grabel’nykh、E. N. Sukhomazova、I. A. Zemirova、N. V. Russavskaya、A. I. Albanov、L. V. Klyba、E. R. Zhanchipova、N. A. Korchevin

  DOI：10.1134/s1070428008100059

  日期：2008.10

  Reactions of 2,3-dibromopropan-1-ol and 1,3-dichloropropan-2-ol with elemental sulfur activated in the system hydrazine hydrate-2-aminoethanol at 30-35C gave oligomeric polysulfides which were subjected to reductive cleavage with formation of individual dithioglycerol isomers. Activation of sulfur with the use of alkali gives rise to mixtures of isomeric products.
• The antioxidant effects of the butterfly cluster [(μ-SeCH2)2CH(OH)]Fe2(CO)6 on radical-induced oxidation of DNA
  作者：Pei-Ze Li、Zai-Qun Liu

  DOI：10.1007/s00044-012-0281-x

  日期：2013.6

  Hydrogenases have been researched in detail, but its protective effect on DNA against radical-induced oxidation was not usually found. [(mu-SeCH2)(2)CH(OH)]Fe-2(CO)(6) (SFOH) and [(mu-SeCH2)(2)CH(OOCCH3)]Fe-2(CO)(6) (SFOA) were synthesized. The hydroxyl group in SFOH was etherized to form SFOA, in which the potential antioxidant group was the [2Fe2Se] cluster. The antioxidant abilities of SFOH and SFOA together with 1,3-dibromo-2-propanol (DBPO) were compared in 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. SFOH can protect DNA concentration dependently and scavenge 4.6 radicals in protecting DNA against AAPH-induced oxidation. However, SFOA and DBPO cannot protect DNA. These results revealed that the aliphatic hydroxyl group in [2Fe2Se] cluster was the antioxidant group of SFOH in protecting DNA against AAPH-induced oxidation. However, the [2Fe2Se] cluster can react with H2O2 to form hydroxyl radical ((OH)-O-center dot), which accelerated the oxidation of DNA. Therefore, the special ability of the [2Fe2Se] cluster may be as a functional group in designing organometallic medicines.