trans-2-(phenylselenenyl)tetrahydrothiophene 1-oxide | 135887-98-8

• 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: trans-2-(phenylselenenyl)tetrahydrothiophene 1-oxide
• 英文别名: (1S,2S)-2-phenylselanylthiolane 1-oxide
• CAS: 135887-98-8
• 化学式: C₁₀H₁₂OSSe
• 分子量: 259.231
• InChiKey: IESJVTCCXGGWPL-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  trans-2-(phenylselenenyl)tetrahydrothiophene 1-oxide 在 偶氮二异丁腈 、 氘代三正丁基锡 作用下， 以 苯 为溶剂， 生成 C₄H₇⁽²⁾HOS 、 C₄H₇⁽²⁾HOS
  参考文献：
  名称：

  Renaud, Philippe; Ribezzo, Marco, Journal of the American Chemical Society, 1991, vol. 113, # 20, p. 7803 - 7805

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,2R)-2-phenylselanylthiolane 1-oxide 生成 trans-2-(phenylselenenyl)tetrahydrothiophene 1-oxide
  参考文献：
  名称：

  Renaud Philippe, Moufid Nadira, Kuo Lung Huang, Curran Dennis P., J. Org. Chem, 59 (1994) N 13, S 3547-3552

  摘要：

  DOI：

文献信息

• Altering the Stereochemistry of Allylation Reactions of Cyclic .alpha.-Sulfinyl Radicals: Effects of Solvents and Lewis Acids
  作者：Philippe Renaud、Nadira Moufid、Lung Huang Kuo、Dennis P. Curran

  DOI：10.1021/jo00092a010

  日期：1994.7

  Full details of the stereochemical outcome of the allylation of the tetrahydrothiophene-2-yl 1-oxide radical in different solvents and in the presence of Lewis acids are reported. Corrections of the cis/trans ratios initially reported in the original communication are presented and the origin for the systematic overestimation of the ratio was found to be the decomposition of the minor cis diastereoisomer during the GC analysis. However, the originally reported stereoselectivity enhancements in the presence of Lewis acids are still valid, although the effects are of smaller amplitudes. The conclusions about an intermediate oxygen-complexed a-sulfinyl radical stand. We report that the very bulky and oxygenophilic methylaluminum diphenoxides (MAD and MABR), recently intoduced by Yamamoto, are perfectly compatible with radical reactions and provide exceptional levels of stereocontrol (up to 98:2) when used stoichiometrically. A good level of stereoselectivity (90:10) was reached by using a catalytic amount of MABR (10%). The yields and the stereoselectivities of the radical allylations compare favorably with the nucleophilic allylation af the deprotonated tetrahydrothiophene 1-oxide.