(1R,2R,6R,R_S)-4-((1S)-isoborneol-10-sulfinyl)-2-methoxy-8-phenyl-8-azabicyclo[4.3.0]non-3-ene-7,9-dione | 209863-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R,2R,6R,R_S)-4-((1S)-isoborneol-10-sulfinyl)-2-methoxy-8-phenyl-8-azabicyclo[4.3.0]non-3-ene-7,9-dione
• 英文别名: (3aR,4R,7aR)-6-[(R)-[(1S,2R,4R)-2-hydroxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]methylsulfinyl]-4-methoxy-2-phenyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione
• CAS: 209863-32-1
• 化学式: C₂₅H₃₁NO₅S
• 分子量: 457.591
• InChiKey: XJPZIDKLRISIKE-WULAFXRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,6R,R_S)-4-((1S)-isoborneol-10-sulfinyl)-2-methoxy-8-phenyl-8-azabicyclo[4.3.0]non-3-ene-7,9-dione 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以50%的产率得到(3aR,7aS)-2-Phenyl-3a,7a-dihydro-4H-isoindole-1,3,5-trione
  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：

  N-苯基马来酰亚胺 、 (R_S,E)-3-[(1S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 在 Eu(fod)3 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (1S,2S,6S,R_S)-4-((1S)-isoborneol-10-sulfinyl)-2-methoxy-8-phenyl-8-azabicyclo[4.3.0]non-3-ene-7,9-dione 、 (1R,2R,6R,R_S)-4-((1S)-isoborneol-10-sulfinyl)-2-methoxy-8-phenyl-8-azabicyclo[4.3.0]non-3-ene-7,9-dione
  参考文献：
  名称：

  Diels–Alder reactions of (RS)-3-[(1S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-dienes with electron-deficient carbodienophiles. The effects of Lewis acid catalysis

  摘要：

  Uncatalyzed cycloadditions of (R-s,E)-1 and (R-s,2)-3-[(1S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 2 with maleimide and N-phenylmaleimide occurred with complete endo and very high facial diastereoselectivities. The effects of Lewis acid catalysis on these Diels-Alder reactions have been evaluated. LiClO4 catalyzed cycloaddition of 1 with dimethyl maleate gave cyclohexene 13 as the unique product with complete control of endo and pi-facial diastereoselectivities exerted by the sulfinyl group. A significant improvement in diastereoselectivity was also observed in the LiClO4 catalyzed cycloaddition of 1 with dimethyl fumarate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00138-4

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。