N-Acetyl-DL-β-<3,4-dihydroxy-phenyl>-alanin | 40332-26-1

• 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-Acetyl-DL-β-<3,4-dihydroxy-phenyl>-alanin
• 英文别名: N-Acetyl-3',4'-dihydroxy-phenyl-alanin；N-acetyl-dopa；2-acetamido-3-(3,4-dihydroxyphenyl)propanoic Acid
• CAS: 40332-26-1
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: RGCLHVKCJVVHLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Acetyl-DL-β-<3,4-dihydroxy-phenyl>-alanin 、 四丁基氢氧化铵 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  手性硫脲盐：在NMR合成，表征和应用对映体的手性含氧阴离子-discrimination †往最‡

  摘要：

  从相对便宜且容易获得的手性胺开始合成手性硫脲和官能化的手性硫脲盐： （S）-甲基苄胺 和松香衍生 （+）-脱氢松香胺。通过硫原子上的烷基化反应将离域的正电荷引入硫脲官能团，可实现动态的旋转异构过程：绕离域的CN和CS键的旋转受阻。因此，可以识别出四种不同的旋转异构体/同分异构体：syn - syn，syn - anti，anti - syn和anti - anti。广泛的1 H和13 C NMR研究表明，在氢键受体溶剂（例如全氘化二甲基亚砜）中，syn – syn构象是优选的。另一方面，当使用非极性溶剂时，例如CDCl 3，的混合物顺式-顺式和顺-反异构体是可检测的，用过量的后者。除此之外，在S-丁基-N的情况下，N′-双（脱氢松香基）硫脲基乙酸乙酯CDCl 3，1 H NMR光谱显示，阴离子和阳离子之间的强分叉氢键导致整体刚性，而在NMR时间尺度上没有观察到阻碍旋转的迹象。这表明这些新的

  DOI：

  10.1039/c2nj40632b

文献信息

• Synthesis of Tripodal Catechol Derivatives Having an Adamantyl Basic Framework for Functionalizing Surfaces
  申请人：Maison Wolfgang

  公开号：US20130245269A1

  公开（公告）日：2013-09-19

  The present invention describes tripodal catechol derivatives with an adamantyl basic framework for the functionalisation of surfaces, methods for their production and use. The remaining fourth bridgehead position is easily suitable to be further functionalised via so-called click reactions, by way of example with biomolecules, dyes, radiomarkers, polyethylene glycol or active agents. The compounds according to the present invention have the general formula X-Ad[(CH 2 ) n —YZ] 3 , wherein A stands for the adamantyl skeleton, X stands for a group —(CH 2 ) p —R 5 , wherein p=0 to 10 and R 5 is selected from —H, —NH 2 , —NO 2 , —OH, —SH, —O—NH 2 , —NH—NH 2 , —N═C═S—, —N═C═O—, —CH═CH 2 , —C≡CH, —COOH, —(C═O)H, —(C═O)R 6 Y stands for —CH 2 —, —CH═CH—, —O—, —S—, —S—S—, —NH—, —O—NH—, —NH—O—, —HC═N—O—, —O—N═CH—, —NR 1 —, -aryl-, -heteroaryl-, —(C═O)—, —O—(C═O)—, —(C═O)—O—, —NH—(C═O)—, —(C═O)—NH—, —NR 1 —(C═O)—, —(C═O)—NR 1 —, —NH—(C═O)—NH—, —NH—(C═S)—NH—, R 1 stands for an alkyl group, R 6 for an alkyl, alkenyl, alkynyl, aryl or heteroaryl group, and Z stands for a catechol derivative. The production of the compounds occurs by reacting a compound X-Ad[(CH 2 ) n —Y′] 3 with a reagent Y″Z to the corresponding compound X-Ad[(CH 2 ) n —YZ] 3 and subsequently purifying the reaction product. Y′ and Y″ are hereby precursors of Y. The compounds according to formula (I) according to the present invention are suitable to be used in a method to functionalise surfaces. The X group of the compounds according to the present invention is suitable to be optionally coupled to an effector, for example, by means of click chemistry.

  本发明描述了具有金刚烷基框架的三脚脚脚酚衍生物，用于功能化表面，以及它们的生产和使用方法。剩余的第四桥头位易于通过所谓的点击反应进一步功能化，例如与生物分子、染料、放射标记物、聚乙二醇或活性剂等。根据本发明的化合物具有一般公式X-Ad[(CH2)n—YZ]3，其中A代表金刚烷骨架，X代表一个基团—(CH2)p—R5，其中p=0到10，R5选自—H、—NH2、—NO2、—OH、—SH、—O—NH2、—NH—NH2、—N═C═S—、—N═C═O—、—CH═CH2、—C≡CH、—COOH、—(C═O)H、—(C═O)R6，Y代表—CH2—、—CH═CH—、—O—、—S—、—S—S—、—NH—、—O—NH—、—NH—O—、—HC═N—O—、—O—N═CH—、—NR1—、-芳基-、-杂环基-、—(C═O)—、—O—(C═O)—、—(C═O)—O—、—NH—(C═O)—、—(C═O)—NH—、—NR1—(C═O)—、—(C═O)—NR1—、—NH—(C═O)—NH—、—NH—(C═S)—NH—，R1代表烷基基团，R6代表烷基、烯基、炔基、芳基或杂环基，Z代表一个邻苯二酚衍生物。化合物的制备通过将化合物X-Ad[(CH2)n—Y′]3与试剂Y″Z反应形成相应的化合物X-Ad[(CH2)n—YZ]3，然后纯化反应产物。Y′和Y″是Y的前体。根据本发明的公式(I)的化合物适用于用于功能化表面的方法中。根据本发明的化合物的X基团适用于可选择地与效应物耦合，例如通过点击化学方法。
• Synthesis of Trivalent Flexible Frameworks with Ligands Comprising Catechol Units for Functionalizing Surfaces
  申请人：Maison Wolfgang

  公开号：US20130245270A1

  公开（公告）日：2013-09-19

  The present invention describes tripodal catechol derivatives with a flexible basic framework for the functionalisation of surfaces, and methods for their production and use. The central atom of the flexible framework is hereby a tertiary aliphatic carbon atom. The remaining fourth bridgehead position is easily suitable to be further functionalised via so-called click reactions, e.g. with biomolecules, dyes, radiomarkers, polyethylene glycol or active agents. The compounds according to the present invention have the general formula X—C[(CH 2 ) n —YZ] 3 , wherein X stands for a group —(CH 2 ) p —R 5 , wherein p=0 to 10 and R 5 is selected from —H, —NH 2 , —NO 2 , —OH, —SH, —O—NH 2 , —NH—NH 2 , —N═C═S—, —N═C═O—, —CH═CH 2 , —C≡CH, —COOH, —(C═O)H, —(C═O)R 6 Y stands for —CH 2 —, —CH═CH—, —C≡C—, —O—, —S—, —S—S—, —NH—, —O—NH—, —NH—O—, —HC═N—O—, —O—N═CH—, —NR 1 —, -Aryl-, -Heteroaryl-, —(C═O)—, —O—(C═O)—, —(C═O)—O—, —NH—(C═O)—, —(C═O)—NH—, —NR 1 —(C═O)—, —(C═O)—NR 1 —, —NH—(C═O)—NH—, —NH—(C═S)—NH—, R 1 stands for an aryl group, R 6 for an alkyl, alkenyl, alkynyl, aryl or heteroaryl group, and Z stands for a catechol derivative. The production of the compounds occurs by reacting a compound X—C[(CH 2 ) n —Y′] 3 with a reagent Y″Z to the corresponding compound X—C[(CH 2 ) n —YZ] 3 and subsequent purification of the reaction product. Y′ and Y″ are hereby precursors of Y. The compounds according to formula (I) according to the present invention are suitable to be used in a method to functionalize surfaces. The X group of the compounds according to the present invention is suitable to be optionally coupled to an effector, for example, by means of click chemistry.

  本发明描述了具有灵活基础结构的三脚猫二酚衍生物，用于表面功能化的方法及其生产和使用方法。灵活框架的中心原子是三级脂肪碳原子。剩余的第四个桥头位置易于通过所谓的点击反应进一步功能化，例如与生物分子、染料、放射性标记物、聚乙二醇或活性剂等进行反应。本发明中的化合物具有一般式X—C[(CH2)n—YZ]3，其中X代表一个群体—(CH2)p—R5，其中p=0至10，R5选自—H、—NH2、—NO2、—OH、—SH、—O—NH2、—NH—NH2、—N═C═S—、—N═C═O—、—CH═CH2、—C≡CH、—COOH、—(C═O)H、—(C═O)R6；Y代表—CH2—、—CH═CH—、—C≡C—、—O—、—S—、—S—S—、—NH—、—O—NH—、—NH—O—、—HC═N—O—、—O—N═CH—、—NR1—、-芳基-、-杂芳基-、—(C═O)—、—O—(C═O)—、—(C═O)—O—、—NH—(C═O)—、—(C═O)—NH—、—NR1—(C═O)—、—(C═O)—NR1—、—NH—(C═O)—NH—、—NH—(C═S)—NH—，其中R1代表芳基，R6代表烷基、烯基、炔基、芳基或杂芳基，Z代表二酚衍生物。该化合物的生产是通过将化合物X—C[(CH2)n—Y']3与试剂Y"Z反应得到相应的化合物X—C[(CH2)n—YZ]3，然后纯化反应产物。Y'和Y"是Y的前体。根据本发明的公式（I）中的化合物适用于用于表面功能化的方法。本发明中化合物的X基团适用于通过点击化学手段可选地与效应物耦合。
• Process and kit for dyeing hair
  申请人：Bristol-Myers Squibb Company

  公开号：EP0658339A1

  公开（公告）日：1995-06-21

  A process for dyeing hair by preparing and applying to the hair an aqueous reaction medium comprising a dopa species, a reactive direct dye and an oxidant, said aqueous reaction medium optionally containing at least one hair dyeing agent selected from primary intermediates and couplers and also containing a buffer to maintain the pH in the range from 6 to 10 during the reaction, and removing said aqueous reaction medium from the hair within about one hour following its preparation.

  一种染发工艺，通过制备一种水性反应介质并将其涂抹在头发上，该反应介质由多巴物、活性直接染料和氧化剂组成，所述水性反应介质可选择含有至少一种选自初级中间体和偶联剂的染发剂，还含有一种缓冲剂，用于在反应过程中将 pH 值保持在 6-10 之间，并在制备后约一小时内从头发上清除所述水性反应介质。
• Topical composition comprising N-acetylaldosamines or N-acetylamino acids
  申请人：Yu, Ruey J., Dr.

  公开号：EP1639994A2

  公开（公告）日：2006-03-29

  Compositions comprising N-acetyl-aldosamines, N-acetylamino acids, and related N-acetyl compounds are useful to alleviate or improve various cosmetic conditions and dermatological disorders, including changes or damage to skin, nail and hair associated with intrinsic aging and/or extrinsic aging, as well as changes or damage caused by extrinsic factors. N-acetyl-aldosamines, N-acetylamino acids, and related N-acetyl composition may further comprise a cosmetic, pharmaceutical or other topical agent to enhance or create synergetic effects.

  包含 N-乙酰-醛胺，N-乙酰基氨基酸和相关 N-乙酰基化合物的组合物可用于缓解或改善各种美容状况和皮肤病，包括与内在老化和/或外在老化相关的皮肤、指甲和头发的变化或损伤，以及由外在因素引起的变化或损伤。N-acetyl-aldosamines, N-acetylamino acids 和相关的 N-acetyl 组合物可进一步包含化妆品、药物或其他外用制剂，以增强或产生协同效应。
• Topical composition comprising n-acetylaldosamines or n-acetylamino acids
  申请人：Yu, Ruey J.

  公开号：EP2080504A2

  公开（公告）日：2009-07-22

  Compositions comprising N-acetyl-aldosamines, N-acetylamino acids, and related N-acetyl compounds are useful to alleviate or improve various cosmetic conditions and dermatological disorders, including changes or damage to skin, nail and hair associated with intrinsic aging and/or extrinsic aging, as well as changes or damage caused by extrinsic factors. N-acetyl-aldosamines, N-acetylamino acids, and related N-acetyl composition may further comprise a cosmetic, pharmaceutical or other topical agent to enhance or create synergetic effects.

  包含 N-乙酰-醛胺，N-乙酰基氨基酸和相关 N-乙酰基化合物的组合物可用于缓解或改善各种美容状况和皮肤病，包括与内在老化和/或外在老化相关的皮肤、指甲和头发的变化或损伤，以及由外在因素引起的变化或损伤。N-acetyl-aldosamines, N-acetylamino acids 和相关的 N-acetyl 组合物可进一步包含化妆品、药物或其他外用制剂，以增强或产生协同效应。