N-(phenylselanyl)morpholine | 82737-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: N-(phenylselanyl)morpholine
• 英文别名: morpholino-benzene-selenenamide；Morpholine, 4-(phenylseleno)-；4-phenylselanylmorpholine
• CAS: 82737-08-4
• 化学式: C₁₀H₁₃NOSe
• 分子量: 242.179
• InChiKey: QVXXUAVKAJXEHW-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C(Press: 0.10 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(phenylselanyl)morpholine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (2Z,4Z)-4-phenylselanylocta-2,4-dienenitrile
  参考文献：
  名称：

  硒化二烯：合成，77 Se NMR立体化学研究和转化为功能化的烯

  摘要：

  2- Phenylselanyl-1,3-二烯3 - 8通过从α-phenylselanylα，β不饱和醛开始维悌希或维悌希-霍纳-埃蒙斯程序制备。通过77 Se和1 H NMR确定每种二烯异构体的比率和构型。然后将这些二烯氧化为亚硒酸盐，在某些情况下可以分离出来。在THF中，[2,3]烯丙基selenoxides，selenimides，和二卤代selenuranes的-sigmatropic重排发生，得到丙二烯基醇12 - 15，丙二烯基氨基甲酸酯16C - 19C，和1-卤代丙二烯20C - 22C，分别。

  DOI：

  10.1016/j.tet.2007.02.082
• 作为产物：
  描述：

  N-(三甲基硅基)吗啉 、 苯基氯化硒 以 二氯甲烷 为溶剂， 以79%的产率得到N-(phenylselanyl)morpholine
  参考文献：
  名称：

  Back, Thomas G.; Kerr, Russell G., Canadian Journal of Chemistry, 1986, vol. 64, p. 308 - 310

  摘要：

  DOI：

文献信息

• 1H,13C,15N,17O and77Se NMR of selenenamides
  作者：Claude Paulmier、Patrice Lerouge、Francis Outurquin、Stella Chapelle、Pierre Granger

  DOI：10.1002/mrc.1260251106

  日期：1987.11

  Numerous areneselenenamides derived from ammonia, primary and secondary amines and two N,N-bis(arylseleno)alkylamines have been studied. The selenenamides bearing an electron-withdrawing substituent on the aromatic moiety are stable. The 1H, 13C and 77Se chemical shifts and some coupling constants are reported. For N.N-dialkyl-o-nitrobenzeneselenenamides, the 77Se NMR and the 17O NMR give evidence of an Se-O interaction. In N-alkyl derivatives, a hydrogen bond between the amine group and the ortho-substituent is proposed to explain the deshielding of the selenium nucleus.

  研究人员对从氨、伯胺和仲胺以及两种 N,N-双（芳基硒）烷基胺中提取的大量硒酰胺进行了研究。在芳香族分子上带有取电子取代基的硒酰胺是稳定的。报告了 1H、13C 和 77Se 化学位移以及一些耦合常数。 对于 N.N-二烷基-邻硝基苯硒酰胺，77Se NMR 和 17O NMR 显示了 Se-O 相互作用的证据。在 N-烷基衍生物中，胺基团和正交取代基之间的氢键被提出来解释硒核的去屏蔽作用。
• An unusual replacement of a methylene moiety by a phenylseleno group. Synthesis of mitomycin C labelled at C-6 by 13CH3 and C2H3
  作者：Masaji Kasai、Hitoshi Arai、Yutaka Kanda

  DOI：10.1039/c39910000600

  日期：——

  A novel replacement of the C-6-methylene group of 7,7-ethylenedioxy-6-methylenemitosane by a phenylseleno group was employed to prepare a critical intermediate in the synthesis of mitomycin C labelled at C-6 by 13CH3 and C2H3.

  利用苯基硒基取代 7,7-ethylenedioxy-6-methylenemitosane 的 C-6-亚甲基这一新颖方法，制备了丝裂霉素 C 合成过程中的一个关键中间体，该中间体的 C-6 被 13CH3 和 C2H3 标记。
• Lerouge, Patrice; Paulmier, Claude, Bulletin de la Societe Chimique de France, 1985, # 6, p. 1219 - 1224
  作者：Lerouge, Patrice、Paulmier, Claude

  DOI：——

  日期：——
• Synthesis and Antitumor Activity of Various 6-Demethylmitomycins and 6-Demethyl-6-halomitomycins
  作者：Hitoshi Arai、Tadashi Ashizawa、Katsushige Gomi、Motomichi Kono、Hiromitsu Saito、Masaji Kasai

  DOI：10.1021/jm00016a005

  日期：1995.8

  A series of 6-demethylmitomycins and 6-demethyl-6-halomitomycins having various mitomycin skeletons were synthesized, taking into account the electronic effect toward the quinone moiety and the partition coefficients. Treatment of enones 15 and 16 with selenenamide or N-halosuccinimide-Et(2)NH afforded the 6-demethyl intermediates 17, 18, and 21-24 via the tandem Michael addition/retro-Mannich reaction sequence. Subsequent conversions into the mitomycin skeletons resulted in the formation of the desired derivatives 7a-c, 8a-c, 11a-c, and 12a,b. These mitomycin derivatives including 3a-c and 4a-c were evaluated for their anticellular activity against HeLa S-3 cells and antitumor activity against Sarcoma 180 in mice. The anticellular activity of 1 and 3a-c depends on the substituent at the C-6 position and the order of increasing activity is H < CH3 < Br < Cl. A similar tendency was observed in their antitumor potency (ED(50)) The activities of 9 and 11a-c also follow a pattern similar to that of 1 and 3a-c. Compounds 4b,c, 8b,c, and 12b having both a halogen at the C-6 position and a methoxy group at the C-7 position did not show the activities because of the instability of the compounds. Interestingly, a correlation between the anticellular activity (IC50) and the partition coefficients (log k') determined by HPLC was observed within the compounds studied except the unstable compounds, while their antitumor activity (ED(50) or T/C) did not correlate with the quinone reduction potential (E(1/2)). These results would indicate the importance of the C-6 substituents and the mitomycin skeletons for exhibiting both anticellular and antitumor activities.
• Synthesis and reactivity of β-phenylselanyl α-oxoesters
  作者：Stéphane Boivin、Francis Outurquin、Claude Paulmier

  DOI：10.1016/s0040-4020(97)10117-x

  日期：1997.12

  beta-Phenylselanyl alpha-oxoesters 2 were prepared by N-phenylselanyl morpholine treatment of alpha-oxoesters 1, oxidized into beta-unsaturated alpha-oxoesters 5 and subjected to the Wittig-Horner olefination. The diethyl (1-phenylselanylalkyl)maleates 6 have led, after [2,3]sigmatropic rearrangement of the corresponding selenoxides, to the diethyl 3-alkylidene-2-hydroxysuccinates 7. The 2-(t-butoxycarbonylamino)-3-alkylidenesuccinates 8 were prepared in a similar way. The decomposition of halo-adducts derived from compounds 6 has allowed the synthesis of the diethyl 3-alkylidene-2-halosuccinates 9 and 10. (C) 1997 Elsevier Science Ltd.