N-(trifluoroacetyl)-L-phenylalanine allyl ester | 133230-43-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(trifluoroacetyl)-L-phenylalanine allyl ester
• 英文别名: prop-2-enyl (2S)-3-phenyl-2-[(2,2,2-trifluoroacetyl)amino]propanoate
• CAS: 133230-43-0
• 化学式: C₁₄H₁₄F₃NO₃
• 分子量: 301.265
• InChiKey: LFIKWJXQAURBSQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(trifluoroacetyl)-L-phenylalanine allyl ester 在 光气 、 barium dihydroxide 、 ammonium hydroxide 、 偶氮二甲酸二异丙酯 、 bis(cyclohexanyl)borane 、 双氧水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 75.58h， 生成 α-benzylprolinamide
  参考文献：
  名称：

  Synthesis of .alpha.-benzyl .gamma.-lactam, .alpha.-benzyl .delta.-lactam, and .alpha.-benzylproline derivatives as conformationally restricted analogs of phenylalaninamide

  摘要：

  The ready availability of N-(trifluoroacetyl)-alpha-allylphenylalaninamide (4) via a dehydration/hetero-Cope rearrangement/ammonolysis sequence starting with N-(trifluoroacetyl)phenylalanine allyl ester made it an attractive intermediate for elaboration into C-alpha to N- or C-alpha to N'bridged products as conformationally restricted phenylalaninamide analogues. Oxidative one-carbon degradation of the side-chain olefin followed by acid-catalyzed silane reduction afforded C-alpha to N'-bridged gamma-lactam. Hydroboration/oxidation of the side-chain olefin provided an intermediate that could be cyclized selectively either to a delta-lactam or a proline analogue depending on choice of dehydrating conditions. For preparation of a target dipeptide containing the alpha-substituted proline moiety, a preferred route involved N-deprotection of 4 and coupling to Boc-Asp(OBn)-OH to give a dipeptide intermediate, which similarly could be elaborated selectively to either the alpha-benzyl delta-lactam analogue or the alpha-benzylproline analogue.

  DOI：

  10.1021/jo00012a022
• 作为产物：
  描述：

  L-苯丙氨酸 在 对甲苯磺酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 N-(trifluoroacetyl)-L-phenylalanine allyl ester
  参考文献：
  名称：

  Synthesis of .alpha.-benzyl .gamma.-lactam, .alpha.-benzyl .delta.-lactam, and .alpha.-benzylproline derivatives as conformationally restricted analogs of phenylalaninamide

  摘要：

  The ready availability of N-(trifluoroacetyl)-alpha-allylphenylalaninamide (4) via a dehydration/hetero-Cope rearrangement/ammonolysis sequence starting with N-(trifluoroacetyl)phenylalanine allyl ester made it an attractive intermediate for elaboration into C-alpha to N- or C-alpha to N'bridged products as conformationally restricted phenylalaninamide analogues. Oxidative one-carbon degradation of the side-chain olefin followed by acid-catalyzed silane reduction afforded C-alpha to N'-bridged gamma-lactam. Hydroboration/oxidation of the side-chain olefin provided an intermediate that could be cyclized selectively either to a delta-lactam or a proline analogue depending on choice of dehydrating conditions. For preparation of a target dipeptide containing the alpha-substituted proline moiety, a preferred route involved N-deprotection of 4 and coupling to Boc-Asp(OBn)-OH to give a dipeptide intermediate, which similarly could be elaborated selectively to either the alpha-benzyl delta-lactam analogue or the alpha-benzylproline analogue.

  DOI：

  10.1021/jo00012a022

文献信息

• Derivatives of tetrapeptides as CCK agonists
  申请人：Abbott Laboratories

  公开号：US05270302A1

  公开（公告）日：1993-12-14

  Selective and potent Type-A CCK receptor agonists of formula (I): X--Y--Z--Q (I) or a pharmaceutically acceptable salt thereof, wherein, X is selected from ##STR1## Y is selected from ##STR2## Z is ##STR3## and Q is ##STR4## or pharmaceutically-acceptable salts thereof, useful in the treatment of gastrointestinal disorders (including gallbladder disorders), central nervous system disorders, insulin-related disorders and pain, as well as in appetite regulation.

  公式（I）的选择性和有效的Type-A CCK受体激动剂为：X--Y--Z--Q（I）或其药学上可接受的盐，其中，X选自##STR1##，Y选自##STR2##，Z为##STR3##，Q为##STR4##或其药学上可接受的盐，可用于治疗胃肠道疾病（包括胆囊疾病）、中枢神经系统疾病、胰岛素相关疾病和疼痛，以及食欲调节。
• Production of N-acyl compounds
  申请人：Braun Max

  公开号：US20060217533A1

  公开（公告）日：2006-09-28

  A process for producing a compound containing an acylated nitrogen atom in which the adduct compound formed from an N-protonated cation and a chloride, bromide or iodide anion or the free nitrogen base is reacted with an acyl halide, preferably an acyl chloride, in the presence of an acid that drives off the released hydrogen chloride (HCl), hydrogen bromide (HBr) or hydrogen iodide (HI).

  一种生产含有酰化氮原子的化合物的工艺，其中由 N-质子化阳离子和氯化物、溴化物或碘化物阴离子或游离氮基形成的加合物与酰基卤化物（最好是酰基氯化物）在一种酸的存在下反应，该酸能驱除释放出的氯化氢（HCl）、溴化氢（HBr）或碘化氢（HI）。
• HOLLADAY, M. W.;NADZAN, A. M., J. ORG. CHEM., 56,(1991) N2, C. 3900-3905
  作者：HOLLADAY, M. W.、NADZAN, A. M.

  DOI：——

  日期：——
• US5270302A
  申请人：——

  公开号：US5270302A

  公开（公告）日：1993-12-14
• [EN] DERIVATIVES OF TETRAPEPTIDES AS CCK AGONISTS
  申请人：ABBOTT LABORATORIES

  公开号：WO1991019733A1

  公开（公告）日：1991-12-26

  (EN) Selective and potent Type-A CCK receptor agonists of formula (I): X-Y-Z-Q, or a pharmaceutically acceptable salt thereof, wherein, X is selected from (a) and (b); Y is selected from (c) and (d); Z is (e); and Q is (f), or pharmaceutically-acceptable salts thereof, useful in the treatment of gastrointestinal disorders (including gallbladder disorders), central nervous system disorders, insuline-related disorders and pain, as well as in appetite regulation.(FR) Agonistes sélectifs et puissants de récepteurs de cholécystokinine du type (A), et répondant à la formule: X-Y-Z-Q, ou l'un de leurs sels pharmaceutiquement acceptables, dans laquelle X est sélectionné parmi (a) et (b); Y est sélectionné parmi (c) et (d); Z représente (e); et Q représente (f); ou leurs sels pharmaceutiquement acceptables, utiles au traitement des troubles gastro-intestinaux (par exemple les troubles de la vésicule biliaire), des troubles du système nerveux central, des troubles associés à l'insuline et de la douleur, ainsi qu'à la régulation de l'appétit.