(2R,5S)-1-Benzyloxycarbonyl-2-hydroxymethyl-5-methylpyrrolidine | 155835-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,5S)-1-Benzyloxycarbonyl-2-hydroxymethyl-5-methylpyrrolidine
• 英文别名: benzyl (2R,5S)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate
• CAS: 155835-36-2
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: QAVFWJGXRHPHAM-WCQYABFASA-N

物化性质

• 沸点：
  386.5±25.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5S)-1-Benzyloxycarbonyl-2-hydroxymethyl-5-methylpyrrolidine 在 吡啶 、 二甲基硫 、 三氧化硫 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,5S)-2-Formyl-5-methyl-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  A short, chirospecific synthesis of the ant venom alkaloid (3R,5S,8S)-3,5-dialkylpyrrolizidines

  摘要：

  The stereospecific synthesis of both (+)-xenovenine (1) and (+)-(3R,5S,8S)-3-methyl-5-(8-nonenyl)pyrrolizidine (2), found in ant venom, is described. The stereoselective intramolecular amidomercuration of the N-alkenylurethane 3, available from D-alanine, followed by oxidative demercuration provides the trans pyrrolidine alcohol 5. Thereafter, oxidation of 5 followed by Horner-Wadsworth-Emmons elongation of the ring appendage affords the relevant bicyclic precursors 7 and 9, which are stereoselectively converted into 1 and 10, respectively, by catalytic hydrogenation. The pyrrolizidine 10 is readily transformed into 2 by elaboration of the side chain at C5.

  DOI：

  10.1021/jo00042a017
• 作为产物：
  描述：

  (S)-(1-methylpent-4-enyl)carbamic acid benzyl ester 生成 (2R,5S)-1-Benzyloxycarbonyl-2-hydroxymethyl-5-methylpyrrolidine
  参考文献：
  名称：

  A short, chirospecific synthesis of the ant venom alkaloid (3R,5S,8S)-3,5-dialkylpyrrolizidines

  摘要：

  The stereospecific synthesis of both (+)-xenovenine (1) and (+)-(3R,5S,8S)-3-methyl-5-(8-nonenyl)pyrrolizidine (2), found in ant venom, is described. The stereoselective intramolecular amidomercuration of the N-alkenylurethane 3, available from D-alanine, followed by oxidative demercuration provides the trans pyrrolidine alcohol 5. Thereafter, oxidation of 5 followed by Horner-Wadsworth-Emmons elongation of the ring appendage affords the relevant bicyclic precursors 7 and 9, which are stereoselectively converted into 1 and 10, respectively, by catalytic hydrogenation. The pyrrolizidine 10 is readily transformed into 2 by elaboration of the side chain at C5.

  DOI：

  10.1021/jo00042a017

文献信息

• A new enantioselective synthesis of trans 2,5-disubstituted pyrrolidine derivatives by radical cyclisation
  作者：Yoko Yuasa、Jun Ando、Shiroshi Shibuya

  DOI：10.1039/c39940000455

  日期：——

  A new and highly enantioselective synthesis of trans 5-substituted 2-hydroxymethylpyrrolidine derivatives is achieved by intramolecular radical cyclization at the 4-position of Δ4,5-oxazolidin-2-one, which leads to C2-symmetrical 2,5-dibenzyloxypyrrolidin-2-one.

  通过在Δ4,5-噁唑烷-2-酮的 4 位进行分子内自由基环化，得到 C2 对称的 2,5-二苄氧基吡咯烷-2-酮，从而实现了反式 5-取代的 2-羟甲基吡咯烷衍生物的新的高对映选择性合成。
• Yuasa, Yoko; Ando, Jun; Shibuya, Shiroshi, Journal of the Chemical Society. Perkin transactions I, 1996, # 5, p. 465 - 473
  作者：Yuasa, Yoko、Ando, Jun、Shibuya, Shiroshi

  DOI：——

  日期：——
• A short, chirospecific synthesis of the ant venom alkaloid (3R,5S,8S)-3,5-dialkylpyrrolizidines
  作者：Hiroki Takahata、Hiroshi Bandoh、Takefumi Momose

  DOI：10.1021/jo00042a017

  日期：1992.7

  The stereospecific synthesis of both (+)-xenovenine (1) and (+)-(3R,5S,8S)-3-methyl-5-(8-nonenyl)pyrrolizidine (2), found in ant venom, is described. The stereoselective intramolecular amidomercuration of the N-alkenylurethane 3, available from D-alanine, followed by oxidative demercuration provides the trans pyrrolidine alcohol 5. Thereafter, oxidation of 5 followed by Horner-Wadsworth-Emmons elongation of the ring appendage affords the relevant bicyclic precursors 7 and 9, which are stereoselectively converted into 1 and 10, respectively, by catalytic hydrogenation. The pyrrolizidine 10 is readily transformed into 2 by elaboration of the side chain at C5.