trans-2-allyltetrahydrothiophene 1-oxide | 135887-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: trans-2-allyltetrahydrothiophene 1-oxide
• 英文别名: (1R,2S)-2-prop-2-enylthiolane 1-oxide
• CAS: 135887-99-9；135888-00-5
• 化学式: C₇H₁₂OS
• 分子量: 144.238
• InChiKey: ZWZVZKIHRHIALP-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-allyltetrahydrothiophene 1-oxide 在 triethyloxonium fluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 cis-2-allyltetrahydrothiophene 1-oxide
  参考文献：
  名称：

  Altering the Stereochemistry of Allylation Reactions of Cyclic .alpha.-Sulfinyl Radicals: Effects of Solvents and Lewis Acids

  摘要：

  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.

  DOI：

  10.1021/jo00092a010
• 作为产物：
  描述：

  烯丙基三丁基锡 、 2-(Phenylseleno)tetrahydrothiophene oxide 以50%的产率得到
  参考文献：
  名称：

  Curran Dennis P., Kuo Lung Huang, J. Org. Chem, 59 (1994) N 12, S 3259-3261

  摘要：

  DOI：

文献信息

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

  DOI：——

  日期：——
• Altering the Stereochemistry of Allylation Reactions of Cyclic .alpha.-Sulfinyl Radicals with Diarylureas
  作者：Dennis P. Curran、Lung Huang Kuo

  DOI：10.1021/jo00091a007

  日期：1994.6

  Radical allylations of 2-(phenylseleno)tetrahydrothiophene oxide and 2-benzyl-5-(phenylseleno)3-isothiazolidone 1-oxide with allyltributylstannane in the presence of N,N-bis[3-(trifluoromethyl)-5-(carbooctyloxy)phenyl] urea have been investigated. This urea was shown to be about as selective at promoting formation of trans-2-allyltetrahydrothiophene oxide and trans-5-allyl-2-benzyl-3-isothiazolidone 1-oxide as hydrogen bonding solvents and Lewis acids.