benzyl (S)-2-allyl-3-phenylpropanoate | 125016-04-8

• 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: benzyl (S)-2-allyl-3-phenylpropanoate
• 英文别名: benzyl 2(S)-benzyl-4-pentenoate；benzyl (2S)-2-benzylpent-4-enoate
• CAS: 125016-04-8
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: CZCMHNRKNAGKDM-SFHVURJKSA-N

物化性质

• 沸点：
  382.7±11.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl (S)-2-allyl-3-phenylpropanoate 在 palladium on activated charcoal sodium chlorite 、 disodium hydrogenphosphate 、 2-甲基-2-丁烯 、 氢气 、 臭氧 作用下， 以 甲醇 、 叔丁醇 为溶剂， 反应 2.92h， 生成 R-2-苄基琥珀酸
  参考文献：
  名称：

  Stereochemistry in enzyme inhibition: synthesis and evaluation of enantiomerically pure 2-benzyl-3-formylpropanoic acids as inhibitors of carboxypeptidase A

  摘要：

  Both enantiomers of 2-benzyl-3-formylpropanoic acid were synthesized in five steps starting with hydrocinnamic acid and each enantiomer assayed for inhibitory activity against carboxypeptidase A to find that the (R)-form is 674-fold more potent than its enantiomer. The finding that the (R)-form which belongs to the L-series is mostly responsible for the inhibitory activity accords with the explanation that the present inhibitor is a transition state analog inhibitor because, as such, its stereochemistry should belong to the same series as that of the substrate, i.e., the L-series. The gem-diol form of the inhibitor generated in situ mimics the transition state in the catalytic process.

  DOI：

  10.1016/s0957-4166(99)00421-8
• 作为产物：
  描述：

  2-benzyl-4-pentenoic acid 在 正丁基锂 、 草酰氯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 benzyl (S)-2-allyl-3-phenylpropanoate
  参考文献：
  名称：

  Stereochemistry in enzyme inhibition: synthesis and evaluation of enantiomerically pure 2-benzyl-3-formylpropanoic acids as inhibitors of carboxypeptidase A

  摘要：

  Both enantiomers of 2-benzyl-3-formylpropanoic acid were synthesized in five steps starting with hydrocinnamic acid and each enantiomer assayed for inhibitory activity against carboxypeptidase A to find that the (R)-form is 674-fold more potent than its enantiomer. The finding that the (R)-form which belongs to the L-series is mostly responsible for the inhibitory activity accords with the explanation that the present inhibitor is a transition state analog inhibitor because, as such, its stereochemistry should belong to the same series as that of the substrate, i.e., the L-series. The gem-diol form of the inhibitor generated in situ mimics the transition state in the catalytic process.

  DOI：

  10.1016/s0957-4166(99)00421-8

文献信息

• Renin-inhibitory oligopeptides, their preparation and use
  申请人：Sankyo Company, Limited

  公开号：US05364844A1

  公开（公告）日：1994-11-15

  Compounds of formula (I): ##STR1## A is a carbon-carbon bond or C.sub.1 -C.sub.3 alkylene; B is imino group or C.sub.1 -C.sub.2 alkylene; R.sup.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, heterocyclic or optionally substituted amino; R.sup.2 is optionally substituted phenyl or optionally substituted naphthyl; R.sup.3 is thiazolyl, isoxazolyl or imidazolyl; R.sup.4 is isopropyl or cyclohexyl; R.sup.5 and R.sup.6 are C.sub.1 -C.sub.4 alkyl, or, together with the carbon atom to which they are attached, C.sub.3 -C.sub.7 cycloalkyl; R.sup.7 is hydrogen, optionally substituted C.sub.1 -C.sub.6 alkyl group; and R.sup.8 is hydrogen or C.sub.1 -C.sub.4 alkyl. These compounds have renin-inhibitory and, hence, hypotensive activities. The invention also provides a method for the treatment or prophylaxis of hypertension induced by failures in the renin-angiotensin system.

  式(I)的化合物: A是碳-碳键或C.sub.1 -C.sub.3烷基; B是亚胺基或C.sub.1 -C.sub.2烷基; R.sup.1是C.sub.1 -C.sub.4烷基，C.sub.1 -C.sub.4烷氧基，杂环或可选择取代的氨基; R.sup.2是可选择取代的苯基或可选择取代的萘基; R.sup.3是噻唑基，异噁唑基或咪唑基; R.sup.4是异丙基或环己基; R.sup.5和R.sup.6是C.sub.1 -C.sub.4烷基，或者与其连接的碳原子一起是C.sub.3 -C.sub.7环烷基; R.sup.7是氢，可选择取代的C.sub.1 -C.sub.6烷基; R.sup.8是氢或C.sub.1 -C.sub.4烷基。这些化合物具有抑制肾素的作用，因此具有降压活性。本发明还提供了一种治疗或预防由于肾素-血管紧张素系统功能障碍引起的高血压的方法。
• Renin inhibitory oligopeptides, their preparation and use
  申请人：Sankyo Company Limited

  公开号：EP0326364B1

  公开（公告）日：1994-06-22
• US5364844A
  申请人：——

  公开号：US5364844A

  公开（公告）日：1994-11-15
• Stereochemistry in enzyme inhibition: synthesis and evaluation of enantiomerically pure 2-benzyl-3-formylpropanoic acids as inhibitors of carboxypeptidase A
  作者：Dong H. Kim、Suhman Chung

  DOI：10.1016/s0957-4166(99)00421-8

  日期：1999.9

  Both enantiomers of 2-benzyl-3-formylpropanoic acid were synthesized in five steps starting with hydrocinnamic acid and each enantiomer assayed for inhibitory activity against carboxypeptidase A to find that the (R)-form is 674-fold more potent than its enantiomer. The finding that the (R)-form which belongs to the L-series is mostly responsible for the inhibitory activity accords with the explanation that the present inhibitor is a transition state analog inhibitor because, as such, its stereochemistry should belong to the same series as that of the substrate, i.e., the L-series. The gem-diol form of the inhibitor generated in situ mimics the transition state in the catalytic process.