2-(hydroxymethyl)phenyl methyl selenide | 6518-77-0

• 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: 2-(hydroxymethyl)phenyl methyl selenide
• 英文别名: 2-(methylselenyl)benzyl alcohol；o-(methylseleno)benzyl alcohol；2-Methylseleno-benzylalkohol；[2-(Methylselanyl)phenyl]methanol；(2-methylselanylphenyl)methanol
• CAS: 6518-77-0
• 化学式: C₈H₁₀OSe
• 分子量: 201.127
• InChiKey: IQPQYWCMWXDMGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-(hydroxymethyl)phenyl methyl selenide 在 氧气 、 二甲基亚砜 作用下， 生成 2-(methylseleno)benzaldehyde
  参考文献：
  名称：

  Ruwet,A.; Renson,M., Bulletin des Societes Chimiques Belges, 1966, vol. 75, p. 157 - 168

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(methylseleno)benzioc acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 2-(hydroxymethyl)phenyl methyl selenide
  参考文献：
  名称：

  Ruwet,A.; Renson,M., Bulletin des Societes Chimiques Belges, 1966, vol. 75, p. 157 - 168

  摘要：

  DOI：

文献信息

• Syntheses and reactions of cyclic se-alkoxy-se-chloroselenuranes and alkoxyselenonium salts
  作者：Tadashi Kataoka、Tatsunori Iwamura、Hisayoshi Tsutsui、Yasuharu Kato、Yoshihiro Banno、Yasuko Aoyama、Hiroshi Shimizu

  DOI：10.1002/hc.1050

  日期：——

  Several 1-chloro-2,1-oxaselenole selenuranes 3a–e and selenonium salts 4a–c and 5-chloro-5,11-epoxy-6,11-dihydrodibenzo[b,e]selenepines 12a and 12b and selenonium salts 13a–c were synthesized, and their reactions with organometallic reagents were studied. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:317–326, 2001

  几种 1-chloro-2,1-oxaselenole selenuranes 3a–e 和硒盐 4a–c 和 5-chloro-5,11-epoxy-6,11-dihydrodibenzo[b,e]selenepines 12a 和 12b 和硒盐 13a–合成了c，并研究了它们与有机金属试剂的反应。© 2001 John Wiley & Sons, Inc. 杂原子化学 12:317–326, 2001
• Intramolecular Nonbonded Interactions Between Divalent Selenium Centers with Donor and Acceptor Substituents
  作者：Alberth Lari、Christian Bleiholder、Frank Rominger、Rolf Gleiter

  DOI：10.1002/ejoc.200900108

  日期：2009.6

  selenide (1), ethynyl 2-(methylselenyl)benzyl selenide (2), and 2-(methylselenyl)benzyl selenocyanate (3). By means of NMR spectroscopic studies we have determined the 77Se NMR chemical shifts of the signals of the Se centers of 1–3 and their long-range 4JSe,Se coupling constants. These results, and the X-ray structural studies of single crystals of 3 and 11, a quasi-dimer of 2, point to an Se···Se van der

  为了研究固态和溶液中两个二价硒中心之间的分子内范德华相互作用，我们制备了甲基 2-（甲基硒基）苄基硒化物（1）、乙炔基 2-（甲基硒基）苄基硒化物（2）和 2 -(甲基硒基)苄基硒氰酸酯(3)。通过核磁共振光谱研究，我们确定了 1-3 硒中心信号的 77Se 核磁共振化学位移及其长程 4JSe,Se 耦合常数。这些结果，以及 3 和 11 单晶的 X 射线结构研究，2 的准二聚体，表明 Se…Se 范德华相互作用和 1-3 中的短 Se…H 距离。这些测量得到了在 MP2/6-311+g(d)//B98/6-311+g(d) 理论水平上 1-3 的量子化学计算的支持，这表明对内切 X 和内切氢构象的偏好1-3。
• Synthese nouvelle et rapide d'alkylseleno et alkyltelluroarenes au moyen d'ethers-couronnes
  作者：André Luxen、Léon Christiaens

  DOI：10.1016/s0040-4039(00)87739-4

  日期：——
• Ruwet,A.; Renson,M., Bulletin des Societes Chimiques Belges, 1966, vol. 75, p. 157 - 168
  作者：Ruwet,A.、Renson,M.

  DOI：——

  日期：——
• Experimental and Theoretical Studies on the Nature of Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms
  作者：Michio Iwaoka、Takayuki Katsuda、Hiroto Komatsu、Shuji Tomoda

  DOI：10.1021/jo048436a

  日期：2005.1.1

  To investigate the nature of weak nonbonded selenium(...)halogen interactions ((SeX)-X-... interactions; X = F Cl, and Br), three types of model compounds [2-(CH2X)C6H4SeY (1-3), 3-(CH2X)-2-C10H6-SeY (4-6), and 2-XC6H4CH2SeY (7-9); Y = CN, Cl, Br, SeAr, and Me] were synthesized, and their Se-77 NMR spectroscopic behaviors were analyzed in CDCl3. The gradual upfield shifts of Se-77 NMR absorptions observed for series 1-3 and 4-6 suggested that the strength of (SeX)-X-... interaction decreases in the order of (SeF)-F-... > (SeCl)-Cl-... > (SeBr)-Br-.... The quantum chemical calculations at the B3LYP/631H level using the polarizable continuum model (PCM) revealed that the most stable conformer for 1-3 is the one with an intramolecular short (SeX)-X-... atomic contact in CHCl3 (epsilon = 4.9) and also that the n(x) --> sigma*(se-y) orbital interaction (E-Se...X) can reasonably explain the order of strength for the (SeX)-X-... interactions. On the other hand, the Se-77 NMR absorptions observed for series 7-9 did not shift significantly from the reference compounds (C6H5CH2SeY), indicating the absence of the (SeX)-X-... interaction for 7-9 presumably due to attenuation of basicity for the halogen atom that is substituted directly to the aromatic ring. These observations suggested that the n(x) --> sigma*(se-y) orbital interaction is a dominant factor for formation of weak (SeX)-X-... interactions. Electron correlation was also suggested to be important for the stability.