3-(N-tert-butyloxycarbonylamino)-4-iodo benzylbutyrate | 247217-25-0

• 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: 3-(N-tert-butyloxycarbonylamino)-4-iodo benzylbutyrate
• 英文别名: Benzyl 4-iodo-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 247217-25-0
• 化学式: C₁₆H₂₂INO₄
• 分子量: 419.259
• InChiKey: AZOOJSICMDXGFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(N-tert-butyloxycarbonylamino)-4-iodo benzylbutyrate 在 sodium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 3-(N-fluorenylmethoxycarbonylamino)-4-cyano benzylbutyrate
  参考文献：
  名称：

  Synthesis and conformation of dipeptide taste ligands containinghomo-β-amino acid residues

  摘要：

  The synthesis and conformational properties of a series of dipeptide taste ligands, differing from the commercial sweetener aspartame by the presence of a methylene group between the C-alpha and the C' carbon atoms (as in homo-beta-residues) in either the L-Asp or the L-Phe residues, are described. Homo-beta-residues such as homo-beta-aspartic acid, homo-beta-phenylglycine and homo-beta-phenylalanine, obtained by homologation of the corresponding proteinogenic alpha-amino acids, have been used in the solution peptide synthesis of the following aspartame analogues in protected and unprotected forms: NH2-homo-beta-(L or D)-Asp-L-Phe-OMe, NH2-L-Asp-homo-beta-L-Phg-OMe and NH2-L-Asp-homo-beta-L-Phe-OMe. Lengthening of the peptide skeleton at the L-Asp site results in a drastic loss of sweetness with the production of tasteless compounds; on the other hand, lengthening of the skeleton at the C-terminal L-Phe site partially mantains the sweet taste in both NH2-L-Asp-homo-beta-L-Phe-OMe and NH2-L-Asp-homo-beta-L-Phg-OMe. The solution conformation of the synthesized dipeptide taste ligands was investigated by NMR and circular dichroism techniques. The analysis of NMR data combined with restrained molecular dynamics calculations shows that all peptides are fairly flexible and they do not assume a preferred conformation in DMSO and methanol. The peptides containing homo-beta-L-Phe and homo-beta-L-Phg do adopt a discrete number of conformations among which mainly extended and 'L-shaped' conformation are represented. The circular dichroism spectra are consistent with the NMR results, indicating a significant flexibility for these compounds. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199907)12:7<577::aid-poc159>3.0.co;2-f
• 作为产物：
  描述：

  3-(N-tert-butyloxycarbonylamino)-4-hydroxy benzylbutyrate 在 咪唑 、 diphenylphosphinopolystyrene 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到3-(N-tert-butyloxycarbonylamino)-4-iodo benzylbutyrate
  参考文献：
  名称：

  Synthesis and conformation of dipeptide taste ligands containinghomo-β-amino acid residues

  摘要：

  The synthesis and conformational properties of a series of dipeptide taste ligands, differing from the commercial sweetener aspartame by the presence of a methylene group between the C-alpha and the C' carbon atoms (as in homo-beta-residues) in either the L-Asp or the L-Phe residues, are described. Homo-beta-residues such as homo-beta-aspartic acid, homo-beta-phenylglycine and homo-beta-phenylalanine, obtained by homologation of the corresponding proteinogenic alpha-amino acids, have been used in the solution peptide synthesis of the following aspartame analogues in protected and unprotected forms: NH2-homo-beta-(L or D)-Asp-L-Phe-OMe, NH2-L-Asp-homo-beta-L-Phg-OMe and NH2-L-Asp-homo-beta-L-Phe-OMe. Lengthening of the peptide skeleton at the L-Asp site results in a drastic loss of sweetness with the production of tasteless compounds; on the other hand, lengthening of the skeleton at the C-terminal L-Phe site partially mantains the sweet taste in both NH2-L-Asp-homo-beta-L-Phe-OMe and NH2-L-Asp-homo-beta-L-Phg-OMe. The solution conformation of the synthesized dipeptide taste ligands was investigated by NMR and circular dichroism techniques. The analysis of NMR data combined with restrained molecular dynamics calculations shows that all peptides are fairly flexible and they do not assume a preferred conformation in DMSO and methanol. The peptides containing homo-beta-L-Phe and homo-beta-L-Phg do adopt a discrete number of conformations among which mainly extended and 'L-shaped' conformation are represented. The circular dichroism spectra are consistent with the NMR results, indicating a significant flexibility for these compounds. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199907)12:7<577::aid-poc159>3.0.co;2-f

文献信息

• [EN] 1, 3-DISUBSTITUTED AZETIDINE DERIVATIVES FOR USE AS CCR-3 RECEPTOR ANTAGONISTS IN THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISEASES<br/>[FR] DERIVES D'AZETIDINE 1, 3-DISUBSTITUES A UTILISER EN TANT QU'ANTAGONISTES DU RECEPTEUR CCR3 DANS LE TRAITEMENT DE MALADIES INFLAMMATOIRES ET ALLERGIQUES
  申请人：NOVARTIS AG

  公开号：WO2005026113A1

  公开（公告）日：2005-03-24

  Compounds of formula Ia or Ib in free or salt form, wherein Ar, X1, X2, m, R1, Q, Y, R2 and R3 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by CCR-3, for example an inflammatory or allergic condition, particularly an inflammatory or obstructive airways disease. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

  公式Ia或Ib的化合物，无论是自由形式还是盐形式，其中Ar、X1、X2、m、R1、Q、Y、R2和R3的含义如规范中所示，可用于治疗由CCR-3介导的疾病，例如炎症或过敏症状，特别是炎症或阻塞性气道疾病。还描述了含有这些化合物的药物组合物以及制备这些化合物的方法。
• N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as ccr33 receptor antagonists
  申请人：——

  公开号：US20040087621A1

  公开（公告）日：2004-05-06

  Compounds of formula (I) in free or salt form, where Ar 1 is phenyl substituted by one or more substituents selected from halogen, cyano, nitro, and C 1 -C 8 -alkyl optionally substituted by cyano or halogen, Ar 2 is phenyl optionally which is unsubstituted or substituted by one or more substituents selected from halogen, cyano, hydroxy, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkoxy or C 1 -C 8 -alkoxycarbonyl, R 1 is C 1 -C 8 -alkyl substituted by hydroxy, C 1 -C 8 -alkoxy, acyloxy, —N(R 2 )R 3 , halogen, carboxy, C 1 -C 8 -alkoxycarbonyl, phenyl-C 1 -C 8 -alkoxycarbonyl, -CON(R 4 )R 5 or by a monovalent cyclic organic group, R 2 and R?3 are each independently hydrogen or C 1 -C 8 -alkyl, or R 2 is hydrogen and R 3 is acyl or SO 2 R 6 , or R 2 and R 3 together with the nitrogen atom to which they are attached denote a 5- or 6-membered heterocyclic group, R 4 and R 5 are each independently hydrogen, C 1 -C 8 -alkyl optionally substituted by hydroxy or phenyl, or phenyl optionally substituted by C 1 -C 8 -alkyl, halogen, cyano or C 1 -C 8 -alkoxy, or R 4 and R 5 together with the nitrogen atom to which they are attached denote a 5- or 6-membered heterocyclic group, R?6 is C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, or phenyl optionally substituted by C 1 -C 8 -alkyl, and n is 1, 2, 3 or 4. The compounds are useful as pharmaceuticals.

  式（I）的化合物，其自由或盐形式，其中Ar1为苯基，取代基选自卤素，氰基，硝基和C1-C8烷基，所述C1-C8烷基可以选择取代氰基或卤素；Ar2为苯基，可以选择不取代或取代基选自卤素，氰基，羟基，硝基，C1-C8烷基，C1-C8卤代烷基，C1-C8烷氧基或C1-C8烷氧羰基；R1为C1-C8烷基，取代基选自羟基，C1-C8烷氧基，酰氧基，-N（R2）R3，卤素，羧基，C1-C8烷氧羰基，苯基-C1-C8烷氧羰基，-CON（R4）R5或单价环状有机基团；R2和R3各自独立地为氢或C1-C8烷基，或R2为氢，R3为酰基或SO2R6，或R2和R3与它们所连接的氮原子一起表示5-或6-成员杂环基团；R4和R5各自独立地为氢，C1-C8烷基，可以选择取代羟基或苯基，或苯基，可以选择取代C1-C8烷基，卤素，氰基或C1-C8烷氧基，或R4和R5与它们所连接的氮原子一起表示5-或6-成员杂环基团；R6为C1-C8烷基，C1-C8卤代烷基或苯基，可以选择取代C1-C8烷基；n为1、2、3或4。该化合物可用于制药。
• Azetidine derivatives as ccr-3 receptor antagonists
  申请人：Le Grand Mark Darren

  公开号：US20050222118A1

  公开（公告）日：2005-10-06

  Compounds of formula I in free or salt form, wherein Ar, X, Y, R 1 , R 2 , R 3 , R 5 , m, n, p and q have the meanings as indicated in the specification, are useful for treating conditions mediated by CCR3. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

  公式I的化合物，无论是自由形式还是盐形式，其中Ar、X、Y、R1、R2、R3、R5、m、n、p和q的含义如规范所示，对于治疗由CCR3介导的疾病是有用的。还描述了包含这些化合物的制药组合物和制备这些化合物的过程。
• 1,3 Disubstituted azetidine derivatives for use as ccr-3 receptor antagonists in the treatment of inflammatory and allergic diseases
  申请人：Le Grand Mark Darren

  公开号：US20070043013A1

  公开（公告）日：2007-02-22

  Compounds of formula Ia or Ib in free or salt form, wherein Ar, X 1 , X 2 , m, R 1 , Q, Y, R 2 and R 3 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by CCR-3, for example an inflammatory or allergic condition, particularly an inflammatory or obstructive airways disease. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

  公式Ia或Ib的化合物，无论是自由形式还是盐形式，其中Ar、X1、X2、m、R1、Q、Y、R2和R3的含义如规范中所示，用于治疗通过CCR-3介导的疾病，例如炎症或过敏性疾病，特别是炎症或阻塞性呼吸道疾病。还描述了含有这些化合物的药物组合物和制备这些化合物的过程。
• N-(4-ARYLOXYPIPERIDIN-1-YLALKYL) CINNAMIC AMIDES AS CCR3-3 RECEPTOR ANTAGONISTS
  申请人：Novartis AG

  公开号：EP1330436A1

  公开（公告）日：2003-07-30