3-[(2S)-1-methyl-4-[(R)-(4-methylphenyl)sulfinyl]pyrrolidin-2-yl]pyridine | 371764-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-[(2S)-1-methyl-4-[(R)-(4-methylphenyl)sulfinyl]pyrrolidin-2-yl]pyridine
• CAS: 371764-94-2
• 化学式: C₁₇H₂₀N₂OS
• 分子量: 300.425
• InChiKey: CKZZJKGYJXVMKY-WURXZWLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(2S)-1-methyl-4-[(R)-(4-methylphenyl)sulfinyl]pyrrolidin-2-yl]pyridine 在 镍 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以67%的产率得到烟碱
  参考文献：
  名称：

  Studies on the diastereoselective allylation of aldehydes with enantiopure 2-sulfinylallyl building blocks

  摘要：

  A comparative study on the allylation of aldehydes with enantiopure (S-S)-2-(p-tolylsulfonyl)-prop-2-en-1-ol (S-S)-1a and the corresponding chloride (S-S)-1b under two different reaction systems is reported. In general, better yields were obtained from chloride (S-S)-1b, whereas higher diastereoinduction was observed from alcohol (S-S)-1a. The sense of diastereoinduction is the same in both systems and the stereochemistry of the major diastereomer has been determined. Moreover, the configurational stability of the sulfoxide group on the resulting sulfinyl homoallylic alcohols 3 has been proven in each reaction system. which demonstrates the efficiency of the sulfoxide group as chiral auxiliary in these allylation processes. Finally. as an example of the synthetic potential of the resulting adducts, a total synthesis of natural enantioenriched (S)-nicotine from sulfinylalcohol 3h is reported, (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00266-x
• 作为产物：
  描述：

  (1R)-4-(methylamino)-3-[(R)-(4-methylphenyl)sulfinyl]-1-pyridin-3-ylbutan-1-ol 在 偶氮二甲酸二异丙酯 、 三乙胺盐酸盐 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到3-[(2S)-1-methyl-4-[(R)-(4-methylphenyl)sulfinyl]pyrrolidin-2-yl]pyridine
  参考文献：
  名称：

  Studies on the diastereoselective allylation of aldehydes with enantiopure 2-sulfinylallyl building blocks

  摘要：

  A comparative study on the allylation of aldehydes with enantiopure (S-S)-2-(p-tolylsulfonyl)-prop-2-en-1-ol (S-S)-1a and the corresponding chloride (S-S)-1b under two different reaction systems is reported. In general, better yields were obtained from chloride (S-S)-1b, whereas higher diastereoinduction was observed from alcohol (S-S)-1a. The sense of diastereoinduction is the same in both systems and the stereochemistry of the major diastereomer has been determined. Moreover, the configurational stability of the sulfoxide group on the resulting sulfinyl homoallylic alcohols 3 has been proven in each reaction system. which demonstrates the efficiency of the sulfoxide group as chiral auxiliary in these allylation processes. Finally. as an example of the synthetic potential of the resulting adducts, a total synthesis of natural enantioenriched (S)-nicotine from sulfinylalcohol 3h is reported, (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00266-x

文献信息

• Studies on the diastereoselective allylation of aldehydes with enantiopure 2-sulfinylallyl building blocks
  作者：Francesc Márquez、Amadeu Llebaria、Antonio Delgado

  DOI：10.1016/s0957-4166(01)00266-x

  日期：2001.7

  A comparative study on the allylation of aldehydes with enantiopure (S-S)-2-(p-tolylsulfonyl)-prop-2-en-1-ol (S-S)-1a and the corresponding chloride (S-S)-1b under two different reaction systems is reported. In general, better yields were obtained from chloride (S-S)-1b, whereas higher diastereoinduction was observed from alcohol (S-S)-1a. The sense of diastereoinduction is the same in both systems and the stereochemistry of the major diastereomer has been determined. Moreover, the configurational stability of the sulfoxide group on the resulting sulfinyl homoallylic alcohols 3 has been proven in each reaction system. which demonstrates the efficiency of the sulfoxide group as chiral auxiliary in these allylation processes. Finally. as an example of the synthetic potential of the resulting adducts, a total synthesis of natural enantioenriched (S)-nicotine from sulfinylalcohol 3h is reported, (C) 2001 Elsevier Science Ltd. All rights reserved.