(S)-(1-methylpent-4-enyl)carbamic acid benzyl ester | 1134776-91-2

• 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: (S)-(1-methylpent-4-enyl)carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-hex-5-en-2-yl]carbamate
• CAS: 1134776-91-2
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: UDCBOIZIOVLMBA-LBPRGKRZSA-N

物化性质

• 沸点：
  355.9±31.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(1-methylpent-4-enyl)carbamic acid benzyl ester 在 吡啶 、 二甲基硫 、 三氧化硫 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-(2R,5S)-1-(benzyloxycarbonyl)-2-methyl-5-(3-oxo-1-decenyl)pyrrolidine
  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：

  L-丙氨酸 生成 (S)-(1-methylpent-4-enyl)carbamic 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

文献信息

• The synthesis of either (+) or (−) trans-2,5-dimethylpyrrolidine
  作者：Richard H. Schlessinger、Edwin J. Iwanowicz

  DOI：10.1016/s0040-4039(00)96049-0

  日期：——

  Trans-2,5-dimethylpyrrolidine, in either optical series, is prepared starting from D or L-alanine in an efficient and reasonably brief reaction sequence.

  从D或L-丙氨酸开始，以有效且合理的简短反应顺序，制备任一光学系列的反式-2,5-二甲基吡咯烷。
• [EN] SMALL MOLECULE BRADYKININ B1 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTE DE FAIBLE MASSE MOLÉCULAIRE DU RÉCEPTEUR B1 DE LA BRADYKININE
  申请人：JERINI AG

  公开号：WO2009036996A3

  公开（公告）日：2009-06-18
• Tetrahydropyridones via intramolecular ureidomercuration
  作者：Samuel Danishefsky、Eiji Taniyama、Robert R. Webb

  DOI：10.1016/s0040-4039(00)81313-1

  日期：1983.1
• DANISHEFSKY, S.;TANIYAMA, E.;WEBB, R. R. ,, II, TETRAHEDRON LETT., 1983, 24, N 1, 11-14
  作者：DANISHEFSKY, S.、TANIYAMA, E.、WEBB, R. R. ,, II

  DOI：——

  日期：——
• SMALL MOLECULE BRADYKININ B1 RECEPTOR ANTAGONISTS
  申请人：Jerini AG

  公开号：EP2195288A2

  公开（公告）日：2010-06-16