1,1-bis(phenylseleno)cyclobutane | 76373-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1-bis(phenylseleno)cyclobutane
• 英文别名: (1-Phenylselanylcyclobutyl)selanylbenzene
• CAS: 76373-62-1
• 化学式: C₁₆H₁₆Se₂
• 分子量: 366.223
• InChiKey: VRRMZQQABSXQPY-UHFFFAOYSA-N

物化性质

• 熔点：
  60 °C
• 沸点：
  425.2±41.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1-bis(phenylseleno)cyclobutane 在 sodium periodate 、 叔丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 18.08h， 生成 1-(hydroxymethyl)cyclobutyl phenyl selenoxide
  参考文献：
  名称：

  Resistance-Modifying Agents. 8. Inhibition of O⁶-Alkylguanine-DNA Alkyltransferase by O⁶-Alkenyl-, O⁶-Cycloalkenyl-, and O⁶-(2-Oxoalkyl)guanines and Potentiation of Temozolomide Cytotoxicity in Vitro by O⁶-(1-Cyclopentenylmethyl)guanine

  摘要：

  A series of O-6-allyl- and O-6-(2-oxoalkyl)guanines were synthesized and evaluated, in comp ari son with the corresponding O-6-alkylguanines, as potential inhibitors of the DNA-repair protein O-6-alkylguanine-DNA alkyltransferase (AGT). Simple O-6-alkyl- and O-6-cycloalkylguanines were weak AGT inactivators compared with O-6-allylguanine (IC50 = 8.5 +/- 0.6 muM) With IC50 values ranging from 100 to 1000 muM. The introduction of substituents at C-2 of the allyl group of O-6-allylguanine reduced activity compared with the parent compound, while analogous compounds in the O-6-(2-oxoalkyl)guanine series exhibited very poor activity (150-1000 muM) O-6-Cycloalkenylguanines proved to be excellent AGT inactivators, with 1-cyclobutenylmethylguanine (IC50 = 0.55 +/- 0.02 muM) and 1-cyclopentenylmethylguanine (IC50 = 0.39 +/- 0.04 muM) exhibiting potency approaching that of the benchmark AGT inhibitor O-6-benzylguanine (IC50 = 0.18 +/- 0.02 muM). 1-Cyclopentenylmethylguanine also inactivated AGT in intact HT29 human colorectal carcinoma cells (IC50 = 0.20 +/- 0.07 muM) and potentiated the cytotoxicity of the monomethylating antitumor agent Temozolomide by approximately 3- and 10-fold, respectively, in the HT29 and Colo205 tumor cell lines. The observation that four mutant AGT enzymes resistant to O-6-benzylguanine also proved strongly cross-resistant to 1-cyclopentenylmethylguanine indicates that the O-6-substituent of each compound makes similar binding interactions within the active site of AGT.

  DOI：

  10.1021/jm000961o
• 作为产物：
  描述：

  溴苯 在 zinc(II) chloride selenium 、 magnesium 作用下， 以 四氯化碳 为溶剂， 反应 4.5h， 生成 1,1-bis(phenylseleno)cyclobutane
  参考文献：
  名称：

  Synthesis of selenoacetals

  摘要：

  DOI：

  10.1016/s0040-4020(01)96719-5

文献信息

• A New Rotane Family:  Synthesis, Structure, Conformation, and Dynamics of [3.4]-, [4.4]-, [5.4]-, and [6.4]Rotane¹
  作者：Lutz Fitjer、Christoph Steeneck、Said Gaini-Rahimi、Ulrike Schröder、Karl Justus、Peter Puder、Martin Dittmer、Carla Hassler、Jörg Weiser、Mathias Noltemeyer、Markus Teichert

  DOI：10.1021/ja973118x

  日期：1998.1.1

  The synthesis, structure, conformation, and dynamics of a new rotane family consisting of four-membered rings are described. All syntheses are based on bicyclobutylidene (9): [2+1] cycloaddition of cyclobutylidene yields [3.4]rotane (5) (9−5), [2+2] cycloaddition of trimethyleneketene followed by spiroalkylation of the resulting trispiroketone 10 yields [4.4]rotane (6) (9−10−13−14−6), homologization

  描述了由四元环组成的新 rotane 家族的合成、结构、构象和动力学。所有合成均基于双环丁叉 (9)：环丁叉的 [2+1] 环加成生成 [3.4] 轮烷 (5) (9-5)，三亚甲基乙烯酮的 [2+2] 环加成，然后将所得三螺酮 10 进行螺烷基化，生成 [3.4] 4.4]rotane (6) (9-10-13-14-6), 10 通过 β-羟基硒化物的同源化可以得到四螺环酮 11 和五螺环酮 12 (10-15-11-16-12), 并进一步详细说明向环丙基卡宾-环丁烯重排产生 [5.4] 轮烷 (7) 和 [6.4] 轮烷 (8) [11(12)-18(24)-19(25)-20(26)-21(27)-22( 28)-23(29)-7(8)]。6, 7, 的结构 和 8 是通过高精度低温 X 射线分析和力场计算确定的，使用搜索程序 HUNTER 与 MM3(92) 相关联。观察到以下特征：从
• α-Selenocyclobutyllithium as a 2-lithio-1,3-diene equivalent. regioselective (100%) synthesis of ipsenol
  作者：S. Halazy、A. Krief

  DOI：10.1016/s0040-4039(00)93667-0

  日期：——
• Synthesis of α-selenoalkyllithium compounds
  作者：A. Krief、W. Dumont、M. Clarembeau、G. Bernard、E. Badaoui

  DOI：10.1016/s0040-4020(01)80063-6

  日期：1989.1
• HALAZY S.; KRIEF A., TETRAHEDRON LETT., 1980, 21, NO 20, 1997-2000
  作者：HALAZY S.、 KRIEF A.

  DOI：——

  日期：——
• KRIEF, A.;DUMONT, W.;CLAREMBEAU, M.;BERNARD, G.;BADAOUI, E., TETRAHEDRON, 45,(1989) N, C. 2005-2022
  作者：KRIEF, A.、DUMONT, W.、CLAREMBEAU, M.、BERNARD, G.、BADAOUI, E.

  DOI：——

  日期：——