(N-carbobenzoxyaminomethyl)methylphosphinic chloride | 154370-40-8

• 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: (N-carbobenzoxyaminomethyl)methylphosphinic chloride
• 英文别名: benzyl N-[[chloro(methyl)phosphoryl]methyl]carbamate
• CAS: 154370-40-8
• 化学式: C₁₀H₁₃ClNO₃P
• 分子量: 261.645
• InChiKey: MMJRCDFOYHPGMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-苯甘氨酸甲酯 盐酸盐 、 (N-carbobenzoxyaminomethyl)methylphosphinic chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-<(N-carbobenzoxyaminomethyl)methyl>phosphinoyl-phenylalanine-methylester
  参考文献：
  名称：

  Peptides containing the novel methylphosphinamide transition-state isostere

  摘要：

  A convenient route towards the synthesis of peptides containing the methylphosphinamide moiety as a novel transition-state isostere of the amide bond hydrolysis is described. The key step being the coupling of a methylphosphinic chloride with an amino acid or peptide protected at the C-terminus. A proper choice of the amino protecting group appeared to be essential.

  DOI：

  10.1016/s0040-4020(01)80258-1
• 作为产物：
  描述：

  N-benzyloxycarbonylaminomethyl(P-methyl)phosphinic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (N-carbobenzoxyaminomethyl)methylphosphinic chloride
  参考文献：
  名称：

  Peptides containing the novel methylphosphinamide transition-state isostere

  摘要：

  A convenient route towards the synthesis of peptides containing the methylphosphinamide moiety as a novel transition-state isostere of the amide bond hydrolysis is described. The key step being the coupling of a methylphosphinic chloride with an amino acid or peptide protected at the C-terminus. A proper choice of the amino protecting group appeared to be essential.

  DOI：

  10.1016/s0040-4020(01)80258-1

文献信息

• [EN] FAR SUPERIOR OXIDATION CATALYSTS BASED ON MACROCYCLIC COMPOUNDS<br/>[FR] CATALYSEURS D'OXYDATION NETTEMENT SUPÉRIEURS À BASE DE COMPOSÉS MACROCYCLIQUES
  申请人：UNIV CARNEGIE MELLON

  公开号：WO2017053564A1

  公开（公告）日：2017-03-30

  An especially robust compound and its derivative metal complexes that are approximately one hundred-fold superior in catalytic performance to the previously invented TAML analogs is provided having the formula (I) wherein Y1, Y2, Y3 and Y4 are oxidation resistant groups which are the same or different and which form 5- or 6-membered rings with a metal, M, when bound to D; at least one Y incorporates a group that is significantly more stable towards nucleophilic attack than the organic amides of TAML activators; D is a metal complexing donor atom, preferably N; each X is a position for addition of a labile Lewis acidic substituent such as (i) H, deuterium, (ii) Li, Na, K, alkali metals, (iii) alkaline earth metals, transition metals, rare earth metals, which may be bound to one or more than one D, (iv) or is unoccupied with the resulting negative charge being balanced by a nonbonded counteraction; at least one Y may contain a site that is labile to acid dissociation, providing a mechanism for shortening complex lifetime. The new complexes deliver catalytic performances that promise to revolutionize multiple oxidation technology spaces including water purification.

  提供了一种特别强大的化合物及其衍生金属配合物，其催化性能大约比先前发明的TAML类似物优越一百倍，其化学式为（I），其中Y1、Y2、Y3和Y4是抗氧化的基团，可以相同也可以不同，并且与金属M结合时形成5-或6-成员环；至少一个Y包含一个对亲核攻击更稳定的基团，比TAML活化剂的有机酰胺更稳定；D是金属络合给体原子，优选为N；每个X是用于添加易失去的Lewis酸性取代基的位置，例如（i）H、氘，（ii）Li、Na、K、碱金属，（iii）碱土金属、过渡金属、稀土金属，可以与一个或多个D结合，（iv）或者未被占据，由非键合的对应作用平衡产生的负电荷；至少一个Y可能包含一个易于酸解离的位点，提供缩短配合物寿命的机制。这些新配合物提供了催化性能，有望彻底改变多种氧化技术领域，包括水净化。
• Far superior oxidation catalysts based on macrocyclic compounds
  申请人：Carnegie Mellon University

  公开号：US10926248B2

  公开（公告）日：2021-02-23

  An especially robust compound and its derivative metal complexes that are approximately one hundred-fold superior in catalytic performance to the previously invented TAML analogs is provided having the formula: wherein Y1, Y2, Y3 and Y4 are oxidation resistant groups which are the same or different and which form 5- or 6-membered rings with a metal, M, when bound to D; at least one Y incorporates a group that is significantly more stable towards nucleophilic attack than the organic amides of TAML activators; D is a metal complexing donor atom, preferably N; each X is a position for addition of a labile Lewis acidic substituent such as (i) H, deuterium, (ii) Li, Na, K, alkali metals, (iii) alkaline earth metals, transition metals, rare earth metals, which may be bound to one or more than one D, (iv) or is unoccupied with the resulting negative charge being balanced by a nonbonded countercation; at least one Y may contain a site that is labile to acid dissociation, providing a mechanism for shortening complex lifetime. The new complexes deliver catalytic performances that promise to revolutionize multiple oxidation technology spaces including water purification.

  一种特别强效的化合物及其衍生物金属配合物的催化性能比之前发明的 TAML 类似物高出约 100 倍，其分子式为 其中 Y1、Y2、Y3 和 Y4 是相同或不同的抗氧化基团，在与 D 结合时与金属 M 形成 5 或 6 元环；至少有一个 Y 含有比 TAML 活化剂的有机酰胺对亲核攻击更稳定的基团；D 是金属络合供体原子，最好是 N；每个 X 都是添加易受路易斯酸性取代基的位置，如 (i) H、氘，(ii) Li、Na、K、碱金属，(iii) 碱土金属、过渡金属、稀土金属，这些取代基可与一个或多个 D 结合，(iv) 或未被占用，由此产生的负电荷由非键反离子平衡；至少一个 Y 可包含一个易受酸解离的位点，为缩短络合物寿命提供了机制。新复合物具有催化性能，有望彻底改变包括水净化在内的多个氧化技术领域。
• OXIDATION CATALYSTS BASED ON MACROCYCLIC COMPOUNDS
  申请人：Carnegie Mellon University

  公开号：EP3353157B1

  公开（公告）日：2021-11-24
• FAR SUPERIOR OXIDATION CATALYSTS BASED ON MACROCYCLIC COMPOUNDS
  申请人：Carnegie Mellon University

  公开号：EP3353157A1

  公开（公告）日：2018-08-01