(2-Methoxyethoxy)methyl phenyl selenide | 152407-19-7

• 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-Methoxyethoxy)methyl phenyl selenide
• 英文别名: 2-methoxyethoxymethyl phenyl selenide；methoxyethoxymethyl phenyl selenide；MEM-phenyl selenide；2-Methoxyethoxymethylselanylbenzene
• CAS: 152407-19-7
• 化学式: C₁₀H₁₄O₂Se
• 分子量: 245.18
• InChiKey: MRVVGHFNJUJPGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  286.4±36.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-Methoxyethoxy)methyl phenyl selenide 在 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 potassium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(trimethylsilyl)ethoxymethyl phenyl selenide
  参考文献：
  名称：

  MOM-, MEM- and SEM-phenyl selenides as reagents for the protection of alcohols as alkoxymethyl ethers

  摘要：

  A simple activation of MOM-, MEM- and SEM-phenyl selenides by iodonium or copper(I) ions in the presence of alcohols to give the corresponding alkoxymethyl ethers is described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.036
• 作为产物：
  描述：

  2-(三氟甲基)苯乙醇 在 sodium tetrahydroborate 、 (CuOTf)*toluene 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (2-Methoxyethoxy)methyl phenyl selenide
  参考文献：
  名称：

  MOM-, MEM- and SEM-phenyl selenides as reagents for the protection of alcohols as alkoxymethyl ethers

  摘要：

  A simple activation of MOM-, MEM- and SEM-phenyl selenides by iodonium or copper(I) ions in the presence of alcohols to give the corresponding alkoxymethyl ethers is described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.036

文献信息

• Generation and Alkylation of .ALPHA.-Lithio-Se,O-heteroacetals, and Stereoselective Cyclization of Olefinic Se,O-Heteroacetals.
  作者：Mitsuhiro YOSHIMATSU、Michiyo FUJIMOTO、Hiroshi SHIMIZU、Mikio HORI、Tadashi KATAOKA

  DOI：10.1248/cpb.41.1160

  日期：——

  Generation of α-lithio-Se, O-heteroacetals was accomplished by direct deprotonation of O-methoxyethylselenoacetals with lithium 2, 2, 6, 6-tetramethylpiperidide. Alkylation of the α-lithioheteroacetals smoothly proceeded to give the products 6 and 7. Olefinic Se, O-heteroacetals 6c and 6d were cyclized via α-seleno carbenium ions generated by selective C-O bond cleavage with titanium tetrachloride to provide the cyclohexane derivatives 8a and 8b, respectively.

  用 2, 2, 6, 6-四甲基哌啶锂直接对 O-甲氧基乙基硒乙醛进行去质子化，生成了 α-硫代-Se，O-杂乙醛。α-硫代杂庚基乙醛的烷基化反应顺利进行，得到产物 6 和 7。烯烃 Se、O-杂乙醛 6c 和 6d 通过四氯化钛选择性 C-O 键裂解生成的 α-硒鎓离子环化，分别得到环己烷衍生物 8a 和 8b。
• A New Method of Generation of .alpha.-Selenocarbenium Ions from Se,O-Heteroacetals and Their Reactions
  作者：Mitsuhiro Yoshimatsu、Takashi Sato、Hiroshi Shimizu、Mikio Hori、Tadashi Kataoka

  DOI：10.1021/jo00084a017

  日期：1994.3

  Various Se,O-heteroacetals were prepared by the LiAlH4 reduction of diselenides 1 followed by alkylation with methoxymethyl chloride or (2-methoxyethoxy)methyl (MEM) chloride. Olefinic and acetylenic alpha-seleno carbenium ions were generated by the selective C-O bond cleavage of O-(2-methoxyethyl)-Se,O-heteroacetals with titanium(IV) chloride and cyclized to give the seleno heterocyclic compounds. Olefinic MEM-selenides 3a,b,d-f,h underwent the endo-mode cyclization to afford 4-chloroselenacycloalkanes 4a,b,d-f,h in good yields, whereas acetylenic MEM-selenides 12b-e,g-j underwent the exo-mode cyclization to give 3-(1-chloroalkylidene)selenacycloalkanes 13b-e,g-j. This new utilization of alpha-seleno carbenium ions was also applied to the intramolecular and intermolecular Friedel-Crafts reactions.
• Yoshimatsu Mitsuhiro, Fujimoto Michiyo, Shimizu Hiroshi, Hori Mikio, Kata+, Chem. and Pharm. Bull, 41 (1993) N 6, S 1160-1162
  作者：Yoshimatsu Mitsuhiro, Fujimoto Michiyo, Shimizu Hiroshi, Hori Mikio, Kata+

  DOI：——

  日期：——