1-(benzylseleno)-4-dodecyl chloroformate | 205436-72-2

• 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-(benzylseleno)-4-dodecyl chloroformate
• 英文别名: 1-Benzylselanyldodecan-4-yl carbonochloridate
• CAS: 205436-72-2
• 化学式: C₂₀H₃₁ClO₂Se
• 分子量: 417.878
• InChiKey: ICWXZWVLRFZNCU-UHFFFAOYSA-N

物化性质

• 沸点：
  472.6±38.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(benzylseleno)-4-dodecyl chloroformate 在 sodium tetrahydroborate 作用下， 以 苯 为溶剂， 反应 48.0h， 生成 2-octyltetrahydroselenophene
  参考文献：
  名称：

  Unexpected Leaving Ability of (Phenyltelluro)formates in the Presence of Internal Nucleophiles:  Complications during Alkyl and Oxyacyl Radical Generation in the Preparation of Sulfur- and Selenium-Containing Heterocycles

  摘要：

  Irradiation of a benzene solution of 1-(benzylseleno)-3-undecyl (phenyltelluro)formate (13) with a 250-W low-pressure mercury lamp leads to the formation of 4-octyl-3-oxaselenan-2-one (18) in good yield. This transformation represents the first reported example of intramolecular homolytic substitution by oxyacyl radicals at selenium. The analogous reaction involving 1-(benzylseleno)-4-dodecyl (phenyltelluro)formate (14) provides a complex mixture of products, while thermolysis of a benzene solution of 14, 1-(benzylseleno)-5-tridecyl (phenyltelluro)formate (15) or 1-(benzylseleno)-6-tetradecyl (phenyltelluro)formate (16) at 160 degrees affords 2-octyltetrahydroselenophene (21), 2-octylselenane (22), and 2-octylselenopane (23) in 43-94% yield, respectively. The formation of the saturated selenium-containing heterocycles 21-23 is most Likely to involve nucleophilic attack by the benzylseleno moiety with (decarboxylative) expulsion of phenyltelluride. The mechanisms of these transformations are discussed.

  DOI：

  10.1021/jo9722111
• 作为产物：
  描述：

  1-Chlorododecan-4-ol 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 1-(benzylseleno)-4-dodecyl chloroformate
  参考文献：
  名称：

  Unexpected Leaving Ability of (Phenyltelluro)formates in the Presence of Internal Nucleophiles:  Complications during Alkyl and Oxyacyl Radical Generation in the Preparation of Sulfur- and Selenium-Containing Heterocycles

  摘要：

  Irradiation of a benzene solution of 1-(benzylseleno)-3-undecyl (phenyltelluro)formate (13) with a 250-W low-pressure mercury lamp leads to the formation of 4-octyl-3-oxaselenan-2-one (18) in good yield. This transformation represents the first reported example of intramolecular homolytic substitution by oxyacyl radicals at selenium. The analogous reaction involving 1-(benzylseleno)-4-dodecyl (phenyltelluro)formate (14) provides a complex mixture of products, while thermolysis of a benzene solution of 14, 1-(benzylseleno)-5-tridecyl (phenyltelluro)formate (15) or 1-(benzylseleno)-6-tetradecyl (phenyltelluro)formate (16) at 160 degrees affords 2-octyltetrahydroselenophene (21), 2-octylselenane (22), and 2-octylselenopane (23) in 43-94% yield, respectively. The formation of the saturated selenium-containing heterocycles 21-23 is most Likely to involve nucleophilic attack by the benzylseleno moiety with (decarboxylative) expulsion of phenyltelluride. The mechanisms of these transformations are discussed.

  DOI：

  10.1021/jo9722111

文献信息

• Unexpected Leaving Ability of (Phenyltelluro)formates in the Presence of Internal Nucleophiles:  Complications during Alkyl and Oxyacyl Radical Generation in the Preparation of Sulfur- and Selenium-Containing Heterocycles
  作者：Mathew A. Lucas、Carl H. Schiesser

  DOI：10.1021/jo9722111

  日期：1998.5.1

  Irradiation of a benzene solution of 1-(benzylseleno)-3-undecyl (phenyltelluro)formate (13) with a 250-W low-pressure mercury lamp leads to the formation of 4-octyl-3-oxaselenan-2-one (18) in good yield. This transformation represents the first reported example of intramolecular homolytic substitution by oxyacyl radicals at selenium. The analogous reaction involving 1-(benzylseleno)-4-dodecyl (phenyltelluro)formate (14) provides a complex mixture of products, while thermolysis of a benzene solution of 14, 1-(benzylseleno)-5-tridecyl (phenyltelluro)formate (15) or 1-(benzylseleno)-6-tetradecyl (phenyltelluro)formate (16) at 160 degrees affords 2-octyltetrahydroselenophene (21), 2-octylselenane (22), and 2-octylselenopane (23) in 43-94% yield, respectively. The formation of the saturated selenium-containing heterocycles 21-23 is most Likely to involve nucleophilic attack by the benzylseleno moiety with (decarboxylative) expulsion of phenyltelluride. The mechanisms of these transformations are discussed.