benzyl (S)-2-benzyl-3-formylpropanoate | 131288-27-2

• 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: benzyl (S)-2-benzyl-3-formylpropanoate
• 英文别名: benzyl (S)-2-benzyl-4-oxobutanoate；(3S)-3-Benzyloxycarbonyl-3-phenylmethylpropanal；benzyl (2S)-2-benzyl-4-oxobutanoate
• CAS: 131288-27-2
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: XUHMQQXARRXYRT-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (S)-2-benzyl-3-formylpropanoate 在 palladium on activated charcoal 氢气 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 potassium (S)-2-benzyl-3-formylpropanoate
  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 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.92h， 生成 benzyl (S)-2-benzyl-3-formylpropanoate
  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

• Heterocyclic peptide renin inhibitors
  申请人：Abbott Laboratories

  公开号：US05164388A1

  公开（公告）日：1992-11-17

  A renin inhibiting compound of the formula ##STR1## wherein X is N, O or CH; R.sub.1 is absent or a functional group; A and L are independently selected from absent, C.dbd.O, SO.sub.2 and CH.sub.2 ; D is C.dbd.O, SO.sub.2 or CH.sub.2 ; Y is N or CH; R.sub.2 is hydrogen, loweralkyl or substituted alkyl; Z is a functional group; R.sub.3 is loweralkyl or substituted alkyl; n is 0 or 1; and T is a mimic of the Leu-Val cleavage site of angiotensinogen; or a pharmaceutically acceptable salt, ester or prodrug thereof.

  公式##STR1##中的一种抑制肾素的化合物，其中X为N、O或CH；R.sub.1为空缺或为一个官能团；A和L分别从空缺、C.dbd.O、SO.sub.2和CH.sub.2中独立选择；D为C.dbd.O、SO.sub.2或CH.sub.2；Y为N或CH；R.sub.2为氢、较低烷基或取代烷基；Z为一个官能团；R.sub.3为较低烷基或取代烷基；n为0或1；T为血管紧张素原Leu-Val裂解位点的模拟物；或其药学上可接受的盐、酯或前药。
• Rhodium-Catalyzed Enantioselective Anti-Markovnikov Hydroformylation of α-Substituted Acryl Acid Derivatives
  作者：Shuailong Li、Zhuangxing Li、Cai You、Xiuxiu Li、Jiaxin Yang、Hui Lv、Xumu Zhang

  DOI：10.1021/acs.orglett.9b04624

  日期：2020.2.7

  Rhodium-catalyzed asymmetric anti-Markovnikov hydroformylation of α-substituted acrylates/acrylamides has been developed. By employing the Rh/(S,S)-DTBM-YanPhos complex, a series of β-chiral linear aldehydes were obtained in high yields (up to 94% yield) and high enantioselectivities (up to 96% ee). The utility of this methodology is demonstrated by a gram-scale reaction and a concise synthetic route

  已经开发出铑催化的α-取代的丙烯酸酯/丙烯酰胺的不对称抗马尔科夫尼科夫加氢甲酰化反应。通过使用Rh /（S，S）-DTBM-YanPhos络合物，可以高收率（最高94％收率）和高对映选择性（最高96％ee）获得一系列β-手性线性醛。该方法的实用性通过克级反应和简明的合成方法制备，证明了手性γ-丁内酯的合成。
• HETEROCYCLIC PEPTIDE RENIN INHIBITORS
  申请人：ABBOTT LABORATORIES

  公开号：EP0439556A1

  公开（公告）日：1991-08-07
• EP0439556A4
  申请人：——

  公开号：EP0439556A4

  公开（公告）日：1991-10-30
• US5164388A
  申请人：——

  公开号：US5164388A

  公开（公告）日：1992-11-17