methyl (S)-3-(benzyloxycarbonylamino)pentanoate | 1181218-10-9

• 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: methyl (S)-3-(benzyloxycarbonylamino)pentanoate
• 英文别名: methyl (3S)-3-(phenylmethoxycarbonylamino)pentanoate
• CAS: 1181218-10-9
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: WWQRRXTXMWTMOI-LBPRGKRZSA-N

物化性质

• 沸点：
  402.4±38.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (S)-3-(benzyloxycarbonylamino)pentanoate 、 1-碘己烷 在 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以8%的产率得到(S)-methyl 2-[(S)-(1-benzyloxycarbonylamino)propyl]octanoate
  参考文献：
  名称：

  Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis

  摘要：

  The first enantioselective organocatalytic alpha-nitroatkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl. nitronate to produce a beta-nitroaldehyde. Two methods, one that furnishes the syn beta-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-alpha,beta-disubstituted beta-amino acids is presented.

  DOI：

  10.1021/ja904504j
• 作为产物：
  描述：

  甲醇 、 氯甲酸苄酯 、 (S)-3-氨基戊酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以97%的产率得到methyl (S)-3-(benzyloxycarbonylamino)pentanoate
  参考文献：
  名称：

  Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis

  摘要：

  The first enantioselective organocatalytic alpha-nitroatkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl. nitronate to produce a beta-nitroaldehyde. Two methods, one that furnishes the syn beta-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-alpha,beta-disubstituted beta-amino acids is presented.

  DOI：

  10.1021/ja904504j

文献信息

• [EN] CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS<br/>[FR] ENTITES ET COMPOSITIONS CHIMIQUES ET METHODES ASSOCIEES
  申请人：CYTOKINETICS INC

  公开号：WO2007056143A2

  公开（公告）日：2007-05-18

  [EN] Compounds useful for treating cellular proliferative diseases and disorders by modulating the activity of one or more mitotic kinesins are disclosed.
  [FR] L'invention concerne des composés qui permettent de traiter des maladies et des troubles cellulaires prolifératifs en modulant l'activité d'une ou de plusieurs kinésines mitotiques.
• Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis
  作者：Jonathan E. Wilson、Anthony D. Casarez、David W. C. MacMillan

  DOI：10.1021/ja904504j

  日期：2009.8.19

  The first enantioselective organocatalytic alpha-nitroatkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl. nitronate to produce a beta-nitroaldehyde. Two methods, one that furnishes the syn beta-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-alpha,beta-disubstituted beta-amino acids is presented.