(3R,4R,5R,R_S)-4,5-dimethoxycarbonyl-1-[(1S)-isoborneol-10-sulfinyl]-3-methoxycyclohexene | 209863-36-5

• 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,4R,5R,R_S)-4,5-dimethoxycarbonyl-1-[(1S)-isoborneol-10-sulfinyl]-3-methoxycyclohexene
• 英文别名: dimethyl (1R,2R,3R)-5-[(R)-[(1S,2R,4R)-2-hydroxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]methylsulfinyl]-3-methoxycyclohex-4-ene-1,2-dicarboxylate
• CAS: 209863-36-5
• 化学式: C₂₁H₃₂O₇S
• 分子量: 428.547
• InChiKey: SYAGJYCDMYLACC-JCCRZNNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R,R_S)-4,5-dimethoxycarbonyl-1-[(1S)-isoborneol-10-sulfinyl]-3-methoxycyclohexene 在 lithium aluminium tetrahydride 、 碘代三甲硅烷 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 19.0h， 生成 (3S,4S,5R)-4,5-dihydroxymethyl-3-hydroxycyclohexanone
  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：

  马来酸二甲酯 、 (R_S,E)-3-[(1S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 在 lithium perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以80%的产率得到(3R,4R,5R,R_S)-4,5-dimethoxycarbonyl-1-[(1S)-isoborneol-10-sulfinyl]-3-methoxycyclohexene
  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