L-Phenylalanine, 2-iodo-, phenylmethyl ester | 1011302-62-7

• 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: L-Phenylalanine, 2-iodo-, phenylmethyl ester
• 英文别名: benzyl (2S)-2-amino-3-(2-iodophenyl)propanoate
• CAS: 1011302-62-7
• 化学式: C₁₆H₁₆INO₂
• 分子量: 381.213
• InChiKey: UDGLQVQTIYLLLW-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-Phenylalanine, 2-iodo-, phenylmethyl ester 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 N-乙基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以94%的产率得到S-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-iodo-phenyl)-propionic acid benzyl ester
  参考文献：
  名称：

  Synthesis of bis‐Phenylalanine, A Novel Eight‐Membered Cyclic Dipeptide

  摘要：

  Cyclic eight-membered ring lactams have been prepared which are formally analogs of Phe-Ala or Ala-Phe dipeptides joined together on their side chains. These are termed bis-phenylalanines because they are phenylalanine with respect to both of the residues in which the phenyl ring is shared between the two. The key synthetic step was the Negishi coupling of Boc-beta-I-Ala methyl ester with a suitably protected 2'-I phenylalanine.

  DOI：

  10.1080/00397910701771090
• 作为产物：
  描述：

  S-Boc-(2-iodo-phenyl)-phenylalanine benzyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以100%的产率得到L-Phenylalanine, 2-iodo-, phenylmethyl ester
  参考文献：
  名称：

  Synthesis of bis‐Phenylalanine, A Novel Eight‐Membered Cyclic Dipeptide

  摘要：

  Cyclic eight-membered ring lactams have been prepared which are formally analogs of Phe-Ala or Ala-Phe dipeptides joined together on their side chains. These are termed bis-phenylalanines because they are phenylalanine with respect to both of the residues in which the phenyl ring is shared between the two. The key synthetic step was the Negishi coupling of Boc-beta-I-Ala methyl ester with a suitably protected 2'-I phenylalanine.

  DOI：

  10.1080/00397910701771090

文献信息

• Process for the preparation of enantiomerically enriched indoline-2-carboxylic acid
  申请人：DSM IP Assets B.V.

  公开号：EP1676838A1

  公开（公告）日：2006-07-05

  The present invention relates to a process for the preparation of an enantiomerically enriched optionally substituted indoline-2-carboxylic acid or a salt thereof, said process comprising subjecting an enantiomerically enriched chiral 2-amino-3-(2-X-substituted aryl)-propionic acid or 2-yl-substituted-amino -3-(2-X-substituted aryl)-propionic acid or a salt thereof, wherein X is a leaving group, to cyclisation, preferably at a temperature of below about 140°C, and in case of the yl-substituted compound, removing said yl-substituent by hydrolysis either prior to or after said cyclisation.

  本发明涉及一种制备对映体富集的可选择取代的吲哚啉-2-羧酸或其盐的过程，该过程包括将对映体富集的手性2-氨基-3-(2-X-取代芳基)-丙酸或2-基取代氨基-3-(2-X-取代芳基)-丙酸或其盐，其中X是一个离去基团，经过环化，优选在约140°C以下的温度下进行，对于基取代化合物，可在环化之前或之后通过水解去除该基取代基团。
• Process for the Preparation of Enantiomerically Enriched Indoline-2-Carboxylic Acid
  申请人：De Vries Andreas Hendrikus Maria

  公开号：US20090043112A1

  公开（公告）日：2009-02-12

  The present invention relates to a process for the preparation of an enantiomerically enriched optionally substituted indoline-2-carboxylic acid or a salt thereof, wherein an enantiomerically enriched chiral ortho-X-substituted phenylalanine compound, wherein X is a leaving group, is subjected to cyclisation, preferably at a temperature of below about 140° C., upon formation of the enantiomerically enriched indoline-2-carboxylic acid compound.

  本发明涉及一种制备对映富集的可选择取代的吲哚-2-羧酸或其盐的过程，其中将对映富集的手性ortho-X-取代苯丙氨酸化合物（其中X是离去基团）进行环化，首选在约140℃以下的温度下进行，形成对映富集的吲哚-2-羧酸化合物。
• PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED INDOLINE-2-CARBOXYLIC ACID
  申请人：DSM IP Assets B.V.

  公开号：EP1833789A1

  公开（公告）日：2007-09-19
• METHOD FOR PRODUCING OPTICALLY ACTIVE PHENYLALANINE COMPOUNDS FROM CINNAMIC ACID DERIVATIVES EMPLOYING A PHENYLALANINE AMMONIA LYASE DERIVED FROM IDIOMARINA LOIHIENSIS
  申请人：DSM IP Assets B.V.

  公开号：EP2069518A1

  公开（公告）日：2009-06-17
• US7732621B2
  申请人：——

  公开号：US7732621B2

  公开（公告）日：2010-06-08