tert-butyl (2S)-2-[(phenylsulfanyl)methyl]pyrrolidine-1-carboxylate | 118656-45-4

• 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: tert-butyl (2S)-2-[(phenylsulfanyl)methyl]pyrrolidine-1-carboxylate
• 英文别名: (S)-N-Boc-2-(thiophenoxymethyl)pyrrolidine；tert-butyl (2S)-2-(phenylsulfanylmethyl)pyrrolidine-1-carboxylate
• CAS: 118656-45-4
• 化学式: C₁₆H₂₃NO₂S
• 分子量: 293.43
• InChiKey: QQDZOOAQZSKLEY-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[(phenylsulfanyl)methyl]pyrrolidine-1-carboxylate 在 sodium cyanoborohydride 、 碳酸氢钠 、 溶剂黄146 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (S)-2-Benzenesulfonylmethyl-1-methyl-pyrrolidine
  参考文献：
  名称：

  Applications of Organosulfur Chemistry to Organic Synthesis:  Total Synthesis of (+)-Himbeline and (+)-Himbacine

  摘要：

  Total syntheses of(+)-himbacine (1) and (+)-himbeline (2) are described. The synthesis involves the preparation of sulfone 38 and aldehyde 42 as single enantiomers followed by coupling of these compounds using a Julia-Lythgoe olefination. The preparation of sulfone 38 features an acid-promoted intramolecular Diels-Alder reaction of an alpha,beta-unsaturated thioester while the synthesis of 42 features a Beak, alkylation of piperidine 39.

  DOI：

  10.1021/jo970612a
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 tert-butyl (2S)-2-[(phenylsulfanyl)methyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of chiral β-amino sulfides and β-amino thiols from α-amino acids

  摘要：

  Bifurcated routes to two series of chiral secondary beta-amino sulfides 5a - c and 11a - c have been developed from L-proIine and (S)-phenylglycine, respectively. The developed methodology has also led to the synthesis of the tertiary beta-amino thiol 7 and the primary beta-amino sulfide 1 2 from L-proline and (S)-phenylglycine, respectively.

  DOI：

  10.1016/0957-4166(95)00197-w

文献信息

• (2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-Catalyzed Efficient Stereoselective Michael Addition of Cyclohexanone and Cyclopentanone to Nitroolefins
  作者：Kamal Singh、Paramjit Singh、Amarjit Kaur、Pushpinder Singh、Sandeep Sharma、Sadhika Khullar、Sanjay Mandal

  DOI：10.1055/s-0032-1316917

  日期：——

  (up to >99:1 dr and >99% ee) without the use of any additive. (2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine, derived from l-proline, has been demonstrated as an efficient organocatalyst for the asymmetric Michael addition of cyclohexanone and cyclopentanone to β-nitrostyrenes. This pyrrolidine-based catalyst bearing a sulfoxide moiety was used to synthesize various γ-nitro carbonyl compounds in high yield

  摘要 衍生自1-脯氨酸的（2 S）-2-[（苯基亚磺酰基）甲基]吡咯烷已被证明是将环己酮和环戊酮不对称迈克尔加成至β-硝基苯乙烯的有效有机催化剂。这种带有亚砜部分的吡咯烷基催化剂被用于以高收率（高达97％）和优异的立体选择性（高达> 99：1 dr和> 99％ee）合成各种γ-硝基羰基化合物。添加剂。 衍生自1-脯氨酸的（2 S）-2-[（苯基亚磺酰基）甲基]吡咯烷已被证明是将环己酮和环戊酮不对称迈克尔加成至β-硝基苯乙烯的有效有机催化剂。这种带有亚砜部分的吡咯烷基催化剂被用于以高收率（高达97％）和优异的立体选择性（高达> 99：1 dr和> 99％ee）合成各种γ-硝基羰基化合物。添加剂。
• New diastereoselective synthesis of oxazolidin-2-ones through carbon-carbon bond formation on cyclic carbamoyloxy radicals
  作者：Shinzo Kano、Tsutomu Yokomatsu、Shiroshi Shibuya

  DOI：10.1021/jo00264a001

  日期：1989.2
• Potent and Selective Nonpeptide Inhibitors of Caspases 3 and 7
  作者：Dennis Lee、Scott A. Long、Jeffrey H. Murray、Jerry L. Adams、Mark E. Nuttall、Daniel P. Nadeau、Kristine Kikly、James D. Winkler、Chiu-Mei Sung、M. Dominic Ryan、Mark A. Levy、Paul M. Keller、Walter E. DeWolf

  DOI：10.1021/jm0100537

  日期：2001.6.1

  5-Dialkylaminosulfonylisatins have been identified as potent, nonpeptide inhibitors of caspases 3 and 7. The most active compound within this series (34) inhibited caspases 3 and 7 in the 2-6 nM range and exhibited approximately 1000-fold selectivity for caspases 3 and 7 versus a panel of five other caspases (1, 2, 4, 6, and 8) and was at least 20-fold more selective versus caspase 9. Sequence alignments of the active site residues of the caspases strongly suggest that the basis of this selectivity is due to binding in the St subsite comprised of residues Tyr204, Trp206, and Phe256 which are unique to caspases 3 and 7. These compounds inhibit apoptosis in three cell-based models: human Jurkat T cells, human chondrocytes, and mouse bone marrow neutrophils.
• KANO, SH.;YOKOMATSU, T.;SHIBUYA, SH., J. ORG. CHEM., 54,(1989) N, C. 513-515
  作者：KANO, SH.、YOKOMATSU, T.、SHIBUYA, SH.

  DOI：——

  日期：——
• Applications of Organosulfur Chemistry to Organic Synthesis:  Total Synthesis of (+)-Himbeline and (+)-Himbacine
  作者：David J. Hart、Jing Li、Wen-Lian Wu、Alan P. Kozikowski

  DOI：10.1021/jo970612a

  日期：1997.7.1

  Total syntheses of(+)-himbacine (1) and (+)-himbeline (2) are described. The synthesis involves the preparation of sulfone 38 and aldehyde 42 as single enantiomers followed by coupling of these compounds using a Julia-Lythgoe olefination. The preparation of sulfone 38 features an acid-promoted intramolecular Diels-Alder reaction of an alpha,beta-unsaturated thioester while the synthesis of 42 features a Beak, alkylation of piperidine 39.