(3R,4S,R_S)-4-(hydroxymethyl)-1-[(1S)-isoborneol-10-sulfinyl]-3-methoxycyclohexene | 290356-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3R,4S,R_S)-4-(hydroxymethyl)-1-[(1S)-isoborneol-10-sulfinyl]-3-methoxycyclohexene
• 英文别名: (1S,2R,4R)-1-[[(R)-[(3R,4S)-4-(hydroxymethyl)-3-methoxycyclohexen-1-yl]sulfinyl]methyl]-7,7-dimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 290356-69-3
• 化学式: C₁₈H₃₀O₄S
• 分子量: 342.5
• InChiKey: ZAERXZCWJRBPTO-UOITVKCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  86
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,R_S)-4-(hydroxymethyl)-1-[(1S)-isoborneol-10-sulfinyl]-3-methoxycyclohexene 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以70%的产率得到(4R)-4-(hydroxymethyl)-cyclohex-2-ene-1-one
  参考文献：
  名称：

  An investigation of the behaviour of α,β-unsaturated sulfoxides in the presence of trimethylsilyl iodide

  摘要：

  A mild, efficient and seemingly general method for converting alpha,beta-unsaturated sulfoxides into carbonyl compounds by means of trimethylsilyl iodide (TMSI) is described. Experiments on different substrates and trimethylsilyl halides lead to the conclusion that the oxidation state of the sulfur atom, on one hand, and halogen kind in TMSX on the other, assume a determining role in the progression of the reaction. The ease of experimental procedure, the possibility of H-1 NMR monitoring, and good yields of final products constitute advantages of the TMSI-promoted conversion of alpha,beta-unsaturated sulfoxides into carbonyl compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01365-0
• 作为产物：
  描述：

  (3R,4R,R_S)-1-[(1S)-isoborneol-10-sulfinyl]-3-methoxy-4-methoxycarbonylcyclohexene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以98%的产率得到(3R,4S,R_S)-4-(hydroxymethyl)-1-[(1S)-isoborneol-10-sulfinyl]-3-methoxycyclohexene
  参考文献：
  名称：

  An investigation of the behaviour of α,β-unsaturated sulfoxides in the presence of trimethylsilyl iodide

  摘要：

  A mild, efficient and seemingly general method for converting alpha,beta-unsaturated sulfoxides into carbonyl compounds by means of trimethylsilyl iodide (TMSI) is described. Experiments on different substrates and trimethylsilyl halides lead to the conclusion that the oxidation state of the sulfur atom, on one hand, and halogen kind in TMSX on the other, assume a determining role in the progression of the reaction. The ease of experimental procedure, the possibility of H-1 NMR monitoring, and good yields of final products constitute advantages of the TMSI-promoted conversion of alpha,beta-unsaturated sulfoxides into carbonyl compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01365-0

文献信息

• Unexpected conversion of vinyl sulfoxides into carbonyl compounds by means of iodotrimethylsilane
  作者：Maria C Aversa、Anna Barattucci、Paola Bonaccorsi、Giuseppe Bruno、Placido Giannetto、Manuela Policicchio

  DOI：10.1016/s0040-4039(00)00612-2

  日期：2000.6

  The unexpected and previously unknown TMSI-promoted conversion of α,β-unsaturated sulfoxides into carbonyl compounds and disulfides is described. It occurs in good yields under mild conditions. The examples provided support the generality and efficiency of this procedure which acts as a good method for removing the sulfinyl group with the advantage of transforming the vinyl sulfoxides into carbonyl

  描述了出乎意料且以前未知的TMSI促进的α，β-不饱和亚砜转化为羰基化合物和二硫化物。在温和条件下产量高。所提供的实施例支持了该方法的一般性和效率，该方法是除去亚磺酰基的良好方法，具有将乙烯基亚砜转化为羰基化合物的优点。