1-tert-butoxycarbonyl-2-(benzenesulfonyl)methylpiperidine | 105495-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-tert-butoxycarbonyl-2-(benzenesulfonyl)methylpiperidine
• 英文别名: tert-butyl 2-(benzenesulfonylmethyl)piperidine-1-carboxylate
• CAS: 105495-25-8
• 化学式: C₁₇H₂₅NO₄S
• 分子量: 339.456
• InChiKey: SEIVMCPOPYOFJS-UHFFFAOYSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  488.8±27.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-tert-butoxycarbonyl-2-(benzenesulfonyl)methylpiperidine 在 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 16.5h， 生成 2-Benzenesulfonylmethyl-1-methyl-piperidine
  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：

  (benzenesulfonyl)methyllithium 在 palladium dihydroxide 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 1-tert-butoxycarbonyl-2-(benzenesulfonyl)methylpiperidine
  参考文献：
  名称：

  Stereoselective Formal Synthesis of Pseudodistomin C

  摘要：

  [GRAPHICS]Trisubstituted benzenesulfonylmethylpiperidine 4, in which the substituents are all cis to each other, is a direct synthetic precursor of the cytotoxic marine alkaloid pseudodistomin C; it has been synthesized with total diastereoselectivities from (S)-pyroglutaminol.

  DOI：

  10.1021/ol010221p

文献信息

• Ridley, Damon D.; Simpson, Gregory W., Australian Journal of Chemistry, 1986, vol. 39, # 4, p. 687 - 698
  作者：Ridley, Damon D.、Simpson, Gregory W.

  DOI：——

  日期：——
• RIDLEY D. D.; SIMPSON G. W., AUSTRAL. J. CHEM., 39,(1986) N 4, 687-698
  作者：RIDLEY D. D.、 SIMPSON G. W.

  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.
• Stereoselective Formal Synthesis of Pseudodistomin C
  作者：Nicole Langlois

  DOI：10.1021/ol010221p

  日期：2002.1.1

  [GRAPHICS]Trisubstituted benzenesulfonylmethylpiperidine 4, in which the substituents are all cis to each other, is a direct synthetic precursor of the cytotoxic marine alkaloid pseudodistomin C; it has been synthesized with total diastereoselectivities from (S)-pyroglutaminol.