(1S)-(-)-N-but-3-enoyl-2,10-camphorsultam | 129568-75-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S)-(-)-N-but-3-enoyl-2,10-camphorsultam
• 英文别名: (2R)-N-(but-3-enoyl)-bornane-10,2-sultam；1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]but-3-en-1-one；1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]but-3-en-1-one
• CAS: 129568-75-8
• 化学式: C₁₄H₂₁NO₃S
• 分子量: 283.392
• InChiKey: ZPEIPWCMKYAHEB-JTNHKYCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-(-)-N-but-3-enoyl-2,10-camphorsultam 在 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 20.0h， 生成 (2R)-N-[(3'R)-3',4'-O-isopropylidenebutanoyl]bornane-10,2-sultam
  参考文献：
  名称：

  Asymmetric syn-dihydroxylation of γ-substituted (2R)-N-(β,γ-enoyl)bornane-10,2-sultams

  摘要：

  Various gamma-substituted (2R)-N-( beta,gamma-enoyl)bornane-10,2-sultams have been examined in diastereoselective OsO4 syn-dihydroxylation. In contrast to the C(alpha)-atom, the bornane-10,2-sultam auxiliary exerts a very poor influence on the C(beta)-carbon. Spontaneous stereoselective hydrolysis of the minor diastereoisomer (3S,4S)-5c opens the way to enantiomerically pure building blocks, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00024-0
• 作为产物：
  描述：

  (2R)-bornane-10,2-sultam 在 三乙胺 、 copper dichloride 作用下， 以 乙腈 、 苯 为溶剂， 反应 19.5h， 生成 (1S)-(-)-N-but-3-enoyl-2,10-camphorsultam
  参考文献：
  名称：

  Asymmetric syn-dihydroxylation of γ-substituted (2R)-N-(β,γ-enoyl)bornane-10,2-sultams

  摘要：

  Various gamma-substituted (2R)-N-( beta,gamma-enoyl)bornane-10,2-sultams have been examined in diastereoselective OsO4 syn-dihydroxylation. In contrast to the C(alpha)-atom, the bornane-10,2-sultam auxiliary exerts a very poor influence on the C(beta)-carbon. Spontaneous stereoselective hydrolysis of the minor diastereoisomer (3S,4S)-5c opens the way to enantiomerically pure building blocks, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00024-0

文献信息

• An access to (Z)-ethylenic pseudodipeptides based on ring-closing metathesis
  作者：Valérie Boucard、Hélène Sauriat-Dorizon、François Guibé

  DOI：10.1016/s0040-4020(02)00795-0

  日期：2002.9

  new access to enantiopure (Z)-ethylenic pseudopeptides, starting from the chiral pool of amino acids and enantiopure 2-substituted-but-3-enoic acids is proposed and illustrated by the syntheses of the (Z)-ethylenic pseudopeptidic analogs of l-Phe-l-Phe, l-Phe-d-Phe, l-Phe-l-Val, l-Phe-d-Val and racemic (ll,dd) and (ld,dl) (phenyl)Gly-Phe. The key-steps of these syntheses are a ring-closing metathesis

  从氨基酸和对映体纯2-取代-丁-3-烯酸的手性库开始，提出了一种新的对映纯（Z）-烯类假肽的途径，并通过I的（Z）-烯类伪肽类似物的合成进行了说明。-Phe-1-Phe，L-Phe-d-Phe，L-Phe-1-Val，L-Phe-d-Val和外消旋（ll，dd）和（ld，dl）（苯基）Gly-Phe。这些合成的关键步骤是由Grubbs的钌烷基炔烃络合物在二乙烯酰胺上催化的闭环复分解反应，以及在温和条件下通过中间形成环状酰亚胺，水解裂解所得的二氢吡啶酮。
• Enantioconservative synthesis and ring closing metathesis of disubstituted dialkenic amides
  作者：Hélène Sauriat-Dorizon、François Guibé

  DOI：10.1016/s0040-4039(98)01432-4

  日期：1998.9

  Optically pure disubstituted dialkenic amides 2, which are direct precursors of Z-ethylenic pseudopeptides 1, are readily synthesized and then cyclized to lactams 3 in the presence of Grubbs' ruthenium-based metathesis catalysts with total conservation of enantiomeric purity. (C) 1998 Elsevier Science Lid. All rights reserved.
• OPPOLZER, WOLFGANG;MORETTI, ROBERT;THOMI, SILVIA, TETRAHEDRON LETT., 30,(1989) N1, C. 5603-5606
  作者：OPPOLZER, WOLFGANG、MORETTI, ROBERT、THOMI, SILVIA

  DOI：——

  日期：——
• Asymmetric syn-dihydroxylation of γ-substituted (2R)-N-(β,γ-enoyl)bornane-10,2-sultams
  作者：Jerzy Raczko、Michal Achmatowicz、Piotr Kwiatkowski、Christian Chapuis、Zofia Urbanczyk-Lipkowska、Janusz Jurczak

  DOI：10.1016/s0957-4166(00)00024-0

  日期：2000.3

  Various gamma-substituted (2R)-N-( beta,gamma-enoyl)bornane-10,2-sultams have been examined in diastereoselective OsO4 syn-dihydroxylation. In contrast to the C(alpha)-atom, the bornane-10,2-sultam auxiliary exerts a very poor influence on the C(beta)-carbon. Spontaneous stereoselective hydrolysis of the minor diastereoisomer (3S,4S)-5c opens the way to enantiomerically pure building blocks, (C) 2000 Elsevier Science Ltd. All rights reserved.