phenyl 6-benzamidohexanoate | 21951-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl 6-benzamidohexanoate
• CAS: 21951-46-2
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: PLYIHJQSXYENMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氨基己酸 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 potassium fluoride 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 35.0h， 生成 phenyl 6-benzamidohexanoate
  参考文献：
  名称：

  Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

  摘要：

  N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.

  DOI：

  10.1021/acs.orglett.5b03061

文献信息

• [EN] PROCESS FOR DIRECT AMIDATION OF AMINES VIA RH(I)-CATALYZED ADDITION OF BOROXINES<br/>[FR] PROCÉDÉ D'AMIDATION DIRECTE D'AMINES PAR AJOUT DE BOROXINES CATALYSÉ AU RH(I)
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2017044043A1

  公开（公告）日：2017-03-16

  This invention relates to a process for making an amide by directly reacting a ferf-butyloxycarbonyl or carboxybenzyl N substituted amine with a boroxine derivative in the presence of a rhodium(l) catalyst, in the presence of a solvent an optionally in the presence of a base. The process provides means to react protected amines to amides using th boroganic reagent without the deprotection of an amine such that it can be directly converted from protected form in on step, and results in good yields in amide formation even for sterically hindered amines. Potassium fluoride is the preferre base in the reaction run in dioxane. Typical rhodium catalysts that can be used include rhodium(l) complex monomer and dimers such as chloro(1,5-cyclooctadiene) rhodium(l) dimer ("[CI(cod)Rh]2") or bis(1,5-cyclooctadiene)rhodium(l trifluoromethanesulfonate ("(cod)2Rh(OTf)").

  这项发明涉及一种通过在铑（Ⅰ）催化剂存在下，在溶剂的存在下和/或在碱的存在下，直接将ferf-丁氧羰基或羧基苄基N-取代胺与硼氧化物衍生物反应，从而制备酰胺的方法。该过程提供了一种反应受保护胺制备酰胺的手段，使用硼有机试剂而无需去保护胺，使得它可以直接从受保护形式转化为酰胺，即使对于立体位阻胺，也能在酰胺形成中获得良好产率。在二氧六环中运行的反应中，氟化钾是首选碱。可用的典型铑催化剂包括铑（Ⅰ）配合物单体和二聚体，如氯代（1,5-环辛二烯）铑（Ⅰ）二聚体（"[CI(cod)Rh]2"）或双（1,5-环辛二烯）铑（Ⅰ）三氟甲磺酸盐（"(cod)2Rh(OTf)"）。
• Preparation of esters
  申请人：THE ASSOCIATED OCTEL COMPANY LIMITED

  公开号：EP0922695A1

  公开（公告）日：1999-06-16

  A process for preparing a phenol ester of formula I (wherein R1 is a linear or branched alkyl or alkenyl group optionally interrupted by an -O- or -NH- group and optionally substituted by an oxo group and L is a group of formula in which R2 is an alkyl group or alkylene chain and Y is a group -CO2-M+, SO3-M+ or PO4-M+ (wherein M is a cation)) comprising the step of reacting a substituted phenol corresponding to L with either (1) a carboxylic acid corresponding to R1CO- in the presence of a chlorinating agent or (2) an acyl chloride corresponding to R1CO- in the presence of a tertiary amine or tertiary amide catalyst.

  一种制备式 I 苯酚酯的工艺 (其中 R1 是任选被-O-或-NH-基团打断并任选被氧代基团取代的直链或支链烷基或烯基，L 是式中的基团 其中 R2 是烷基或亚烷基链，Y 是基团-CO2-M+、SO3-M+ 或 PO4-M+（其中 M 是阳离子）），包括以下步骤：使与 L 相对应的取代苯酚与(1)与 R1CO- 相对应的羧酸在氯化剂存在下反应，或(2)与 R1CO- 相对应的酰基氯在叔胺或叔酰胺催化剂存在下反应。