N-(t-butyloxycarbonyl)-4-(1-naphthyl)-L-phenylalanine methyl ester | 137255-89-1

• 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-(t-butyloxycarbonyl)-4-(1-naphthyl)-L-phenylalanine methyl ester
• 英文别名: N-[(1,1-Dimethylethoxy)carbonyl]-4-(1-naphthalenyl)-L-phenylalanine methyl ester；methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-naphthalen-1-ylphenyl)propanoate
• CAS: 137255-89-1
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: URFUEIGCCAZEGV-QFIPXVFZSA-N

物化性质

• 沸点：
  562.2±50.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  N-(t-butyloxycarbonyl)-4-(1-naphthyl)-L-phenylalanine methyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以93%的产率得到(S)-4-(1-naphthalenyl)phenylalanine methyl ester hydrochloride salt
  参考文献：
  名称：

  A simple asymmetric synthesis of 4-arylphenylalanines via palladium-catalyzed cross coupling reaction of arylboronic acids with tyrosine triflate

  摘要：

  DOI：

  10.1021/jo00027a066
• 作为产物：
  描述：

  Boc-L-酪氨酸甲酯 在 四(三苯基膦)钯 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 N-(t-butyloxycarbonyl)-4-(1-naphthyl)-L-phenylalanine methyl ester
  参考文献：
  名称：

  A simple asymmetric synthesis of 4-arylphenylalanines via palladium-catalyzed cross coupling reaction of arylboronic acids with tyrosine triflate

  摘要：

  DOI：

  10.1021/jo00027a066

文献信息

• Production method for biarylalanine
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20040024229A1

  公开（公告）日：2004-02-05

  There is provided a production method for producing a biarylalanine compound of formula (4): 1 wherein R 1 represents a amino protective group and R 2 represents an amino protective group or a hydrogen atom, R 3 is a carboxy protective group, or the like, and R 4 is a substituted or unsubstituted aryl or heteroaryl group, characterized by reacting an aromatic amino acid of formula (1) 2 wherein X is a halogen atom or a trifluoromethanesulfonyloxy group, and R 1 , R 2 and R 3 has the same meaning as defined above, with an organic boron compound of formula (2): 3 wherein R 4 has the same meaning as defined above, and Q 1 and Q 2 are the same or different and each is a hydroxy group, an alkoxy group having 1 to 4 carbon atom(s), in the presence of nickel catalyst and a base.

  提供一种生产生产式（4）的联苯丙氨酸化合物的生产方法： 其中R1代表氨基保护基，R2代表氨基保护基或氢原子，R3是羧基保护基等，R4是取代或未取代的芳基或杂芳基，其特征在于将式（1）的芳香族氨基酸： 其中X是卤素原子或三氟甲磺氧基团，R1、R2和R3的含义与上述定义相同，与式（2）的有机硼化合物反应： 其中R4的含义与上述定义相同，Q1和Q2相同或不同，每个都是羟基、具有1至4个碳原子的烷氧基，在镍催化剂和碱的存在下。
• An Efficient Synthesis of 4-Aryl and 4-Vinylphenylalanines by Stille Cross-Coupling Reaction
  作者：Enrico Morera、Giorgio Ortar

  DOI：10.1055/s-0030-1260179

  日期：——

  The palladium-catalyzed reaction of N-Boc-4-trimethyl-stannyl-L-phenylalanine methyl ester (1) with a variety of aryl and vinyl iodides and triflates (2) affords the corresponding 4-aryl and 4-vinylphenylalanines 3 in synthetically useful yields.

  在钯催化下，N-叔丁氧羰基-4-三甲基锡-L-苯丙氨酸甲酯（1）与多种芳基和乙烯基碘化物和三酸盐（2）发生反应，生成相应的 4-芳基和 4-乙烯基苯丙氨酸 3，合成产率高。
• Process for preparing a biaryl compound
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20040158093A1

  公开（公告）日：2004-08-12

  A process for preparing an optically active biaryl compound the formula (4): 1 wherein R*, R 2 , R 3 , n 1 , n 2 and * are as defined hereinafter, which comprises reacting an aromatic sulfonic acid ester compound of the formula (1): 2 wherein R 1 is a substituted or unsubstituted alkyl or aryl group, R 2 is the same or different and represents a fluorine atom, a cyano group, a nitro group, a substituted or unsubstituted linear or branched alkyl group, etc., R* is the same or different and represents a substituent having at least one asymmetric carbon, or the substituents on the adjacent carbon atoms of the benzene ring may be bound each other and taken together with the benzene ring to form a fused polycyclic aromatic ring, and provided that R 1 is not a trifluoromethyl group, a nonafluorobutyl group or a pentafluorophenyl group, with an organic boron compound of the formula (2): 3 wherein R 3 is a substituted or unsubstituted aryl or heteroaryl group, and Q 1 and Q 2 are the same or different and each is a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, etc., at 70° C. or below in the presence of a nickel catalyst and a base.

  一种制备光学活性双芳基化合物的方法，其化学式为（4）：1，其中R*，R2，R3，n1，n2和*的定义如下，包括将化学式（1）的芳香磺酸酯化合物与化学式（2）的有机硼化合物在镍催化剂和碱存在下，在70°C以下反应，其中：化学式（1）中，R1为取代或未取代的烷基或芳基基团，R2相同或不同，表示氟原子、氰基、硝基、取代或未取代的直链或支链烷基等；R*相同或不同，表示具有至少一个不对称碳的取代基，或相邻苯环碳原子上的取代基可以彼此结合并与苯环一起形成螺环多环芳香环。但R1不是三氟甲基基团、九氟丁基基团或五氟苯基团；化学式（2）中，R3为取代或未取代的芳基或杂环芳基团，Q1和Q2相同或不同，分别为羟基、具有1到4个碳原子的烷氧基等。
• Intermediate for preparing a biaryl compound
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2161254A1

  公开（公告）日：2010-03-10

  An optically active compound of formula (la'): wherein R10 is a substituted or unsubstituted alkyl or aryl group, R11 is a substituted or unsubstituted alkoxycarbonyl group, R12 is a hydrogen atom, R13 is a C1-C4 alkyl group, n11, n12 and n13 are each independently 0 or 1, the carbon atom marked with * is an asymmetric carbon atom, provided that R10 is not a trifluoromethyl group, a nonafluorobutyl group or a pentafluorophenyl group; and a process for preparing the same.

  式(la')的光学活性化合物： 其中 R10 是取代或未取代的烷基或芳基、 R11 是取代或未取代的烷氧羰基 R12 是氢原子 R13 是 C1-C4 烷基、 n11、n12 和 n13 各自独立地为 0 或 1、 标有 * 的碳原子是不对称碳原子、 条件是 R10 不是三氟甲基、无氟丁基或五氟苯基；以及制备该物质的工艺。
• PROCESS FOR THE PREPARATION OF BIARYL COMPOUNDS
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1481967B1

  公开（公告）日：2011-05-04