(S)-1-phenylethyl acetoacetate | 132679-10-8

• 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: (S)-1-phenylethyl acetoacetate
• 英文别名: 1-phenylethyl acetoacetate；[(1S)-1-phenylethyl] 3-oxobutanoate
• CAS: 132679-10-8
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: GSBJXOIVIOYPOW-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (S)-1-phenylethyl acetoacetate 、 氨 生成 [(1S)-1-phenylethyl] (E)-3-aminobut-2-enoate
  参考文献：
  名称：

  YAMAGUTI, XISAO;KANNO, XIDEHO;XASEHGAVA, MASAITI;KATAOKA, KEHNITIRO;OKAMI+

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯基乙基乙酰乙酸酯 以36%的产率得到
  参考文献：
  名称：

  HUDLICKY, TOMAS;TSUNODA, TOSHIYA;GADAMASETTI, KUMAR G.;MURRY, JERRY A.;KE+, J. ORG. CHEM., 56,(1991) N1, C. 3619-3623

  摘要：

  DOI：

文献信息

• SUBSTITUTED HETEROCYCLIC COMPOUNDS AS ION CHANNEL MODULATORS
  申请人：Abelman Matthew

  公开号：US20100125091A1

  公开（公告）日：2010-05-20

  The present invention relates to sodium channel inhibitors of Formula (I): in which R 1 , R 2 , R 3 , R 4 , R 5 , X, Y, and Z are as defined herein, and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. The invention also relates to methods for the preparation of the compounds, and to pharmaceutical compositions containing such compounds.

  本发明涉及具有以下结构的钠通道抑制剂（I）：其中R1、R2、R3、R4、R5、X、Y和Z如本文所定义，并且其在治疗各种疾病状态中的使用，包括心血管疾病和糖尿病。该发明还涉及制备这些化合物的方法，以及含有这些化合物的药物组合物。
• Process for the enantioselective preparation of secondary alcohols by lipase-catalyzed solvolysis of the corresponding acetoacetic esters
  申请人：Popp Alfred

  公开号：US20050032182A1

  公开（公告）日：2005-02-10

  Process for the enantioselective preparation of secondary alcohols, wherein a racemic or enantiomerically enriched mixture of acetoacetic esters of chiral secondary alcohols is subjected to enantioselective enzymatic solvolysis in the presence of a nucleophile and a lipase capable of the solvolytic cleavage of an ester group.

  手性二级醇的对映选择性制备过程，其中手性二级醇的乙酰乙酸酯的混合物（消旋或对映富集）在核苷酸和一种能够溶解酯基的脂肪酶存在下，经过对映选择性酶促溶解反应。
• Structural Modifications of Nimodipine Lead to Novel PDE1 Inhibitors with Anti-pulmonary Fibrosis Effects
  作者：Meng-Xing Huang、Yi-Jing Tian、Chuan Han、Run-Duo Liu、Xi Xie、Yijun Yuan、Yi-Yi Yang、Zhe Li、Jianwen Chen、Hai-Bin Luo、Yinuo Wu

  DOI：10.1021/acs.jmedchem.2c00458

  日期：2022.6.23

  previous research demonstrated that phosphodiesterase-1 (PDE1) could work as a potential target against idiopathic pulmonary fibrosis. Nimodipine, a calcium antagonist commonly used to improve hypertension, was reported to have inhibition against PDE1. Herein, a series of nimodipine analogues were discovered as novel selective and potent PDE1 inhibitors after structural modifications. Compound 2g exhibited

  我们之前的研究表明，磷酸二酯酶 1 (PDE1) 可以作为对抗特发性肺纤维化的潜在靶点。据报道，尼莫地平是一种常用于改善高血压的钙拮抗剂，对 PDE1 有抑制作用。在此，一系列尼莫地平类似物被发现是经过结构修饰后的新型选择性和有效的 PDE1 抑制剂。化合物2g对 PDE1C 表现出优异的抑制活性 (IC 50 = 10 nM)，对除 PDE4 之外的其他 PDE 具有高选择性，并且具有较弱的钙通道拮抗活性。复方2g给药在博莱霉素诱导的肺纤维化大鼠模型中表现出显着的治疗作用，并阻止了TGF-β1诱导的肌成纤维细胞分化。发现PDE1B和PDE1C的表达增加并集中在纤维化病灶。化合物2g增加了肺纤维化大鼠肺中 3',5'-环磷酸腺苷 (cAMP) 和 3',5'-环磷酸鸟苷 (cGMP) 的水平, 支持了抗纤维化作用的事实。2g均通过cAMP和cGMP的调节。
• Verfahren zur enantioselektiven Herstellung von sekundären Alkoholen durch lipasenkatalysierte Solvolyse der korrespondierenden Acetessigester
  申请人：Consortium für elektrochemische Industrie GmbH

  公开号：EP1505156A1

  公开（公告）日：2005-02-09

  Verfahren zur enantioselektiven Herstellung von sekundären Alkoholen, dadurch gekennzeichnet, dass ein racemisches oder enantiomerenangereichertes Gemisch von Acetessigsäureestern chiraler sekundärer Alkohole einer enantioselektiven enzymatischen Solvolyse in Gegenwart eines Nucleophils und einer zur solvolytischen Spaltung einer Estergruppe befähigten Lipase unterworfen wird.

  一种对映体选择性制备仲醇的工艺，其特征在于将手性仲醇的外消旋或对映体富集的乙酰乙酸酯混合物在亲核剂和能溶解裂解酯基的脂肪酶存在下进行对映体选择性酶解。
• Yeast-mediated resolution of .beta.-keto esters of prochiral alcohols
  作者：Tomas Hudlicky、Toshiya Tsunoda、Kumar G. Gadamasetti、Jerry A. Murry、Gary E. Keck

  DOI：10.1021/jo00011a031

  日期：1991.5

  Several racemic alcohols were converted to their beta-keto esters with diketene, and the resulting compounds were subjected to kinetic resolution by means of bakers' yeast. The unreacted keto esters were separated from the reduced hydroxy esters by chromatography, and the products were analyzed for levels of enantiomeric excess. Chiral shift reagents, Mosher esters, and optical rotation of the enantiomers of the alcohols were the criteria used to determine the optical integrity of the resolved alcohols after hydrolysis of the esters. Absolute stereochemistry was determined for the resolution products of all the substrates. Some rationale is advanced to account for the observed levels of enantiomeric excess and for the apparent diastereospecificity of the enzymatic resolution. The utility of this process as means of resolution of prochiral alcohols as well as an application of such resolution to the preparation of both enantiomers of a pyrrolizidine alkaloid synthon are indicated.