2-benzyloxycarbonyloxyimino-2-phenylacetonitrile | 59577-42-3

• 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: 2-benzyloxycarbonyloxyimino-2-phenylacetonitrile
• 英文别名: benzyl [[cyano(phenyl)methylidene]amino] carbonate
• CAS: 59577-42-3
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: KOZNRINGOBVQEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  71.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzyloxycarbonyloxyimino-2-phenylacetonitrile 在 三乙烯二胺 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 72.0h， 生成 Z-ΔAba-Gly-OBzl
  参考文献：
  名称：

  Studies on 2-Aziridinecarboxylic Acid. VII. Formation of Dehydroamino Acid PeptidesviaIsomerization of Peptides Containing 2-Aziridinecarboxylic Acid by Tertiary Amines

  摘要：

  含有 1-(α-氨基酰基)-2-氮丙啶羧酸的肽经叔胺、三乙胺或 1,4-二氮杂双环[2.2.2]辛烷（Dabco）处理后异构化成相应的脱氢氨基酸肽。用叔胺处理苄氧羰基-2-氮丙啶羧酸衍生物也可制备脱氢海因衍生物。

  DOI：

  10.1246/bcsj.55.3232
• 作为产物：
  描述：

  2-羟亚氨基-2-苯乙腈 、 氯甲酸苄酯 生成 2-benzyloxycarbonyloxyimino-2-phenylacetonitrile
  参考文献：
  名称：

  Peptides. VI. Some Oxime Carbonates as Novelt-Butoxycarbonylating Reagents

  摘要：

  几种肟的叔丁氧羰基衍生物是通过相应的肟基碳酸氯制备的。其中，二乙基（叔丁氧羰氧亚氨基）丙二酸酯和2-（叔丁氧羰氧亚氨基）-2-苯基乙腈被用于在不同条件下制备叔丁氧羰氨基酸。结果总结在一个表格中。

  DOI：

  10.1246/bcsj.50.718

文献信息

• Studies on 2-Aziridinecarboxylic Acid. VIII. Total Synthesis of Actinomycin D and Its Serine Analogue<i>via</i>Ring-opening Reaction of 1-Benzyloxycarbonyl-2-aziridinecarboxylic Acid Moiety
  作者：Kiichiro Nakajima、Takumi Tanaka、Masahiro Neya、Kenji Okawa

  DOI：10.1246/bcsj.55.3237

  日期：1982.10

  Direct synthesis of peptides containing 1-benzyloxycarbonyl-2-aziridinecarboxylic acid were carried out by the reaction of β-hydroxy-α-amino acid peptides with DEAD–TPP reagents, and key O-peptide intermediates of actinomycin D synthesis were prepared via a ring-opening reaction of the aziridine with N-protected dipeptide. Peptide lactone was prepared by the DCC–HOBt method, and the subsequent debenzyl procedure and oxydation procedure gave the title compounds in good yields.

  通过β-羟基-α-氨基酸肽与DEAD-TPP试剂的反应，直接合成了含有1-苄氧羰基-2-氮丙啶羧酸的肽，并通过氮丙啶与N-保护二肽的开环反应，制备了放线菌素D合成的关键O肽中间体。用 DCC-HOBt 法制备了肽内酯，随后的去苄基程序和氧化程序以良好的收率得到了标题化合物。
• Synthesis of<i>α</i>-Aminophosphonic Octapeptide, Phe–Gly–Ser–Leu–Ala^P–Phl–Leu–Pro, an Analog with Partial Sequence of<i>erb</i>B-2 Gene Product
  作者：Kaoru Inami、Tadashi Teshima、Hideaki Miyashita、Tetsuo Shiba

  DOI：10.1246/bcsj.68.942

  日期：1995.3

  A chemical synthesis was performed of an octapeptide with a phosphonic ester linkage, which corresponds to a variation of the partial sequence of a gene product of erb B-2. The phosphonic ester linkage was successfully prepared through a coupling reaction of magnesium salt of the hydroxypeptide with phosphonochloridate, without damage of the peptide bond. The free aminophosphonic peptide as the final product gave a single peak on the ODS column, and a reasonable ratio of the component amino acids. The reaction series exploited here might be useful as a general procedure for preparation of the phosphonic peptide.

  对具有膦酸酯键的八肽进行了化学合成，其对应于erb B-2基因产物的部分序列的变体。通过羟基肽的镁盐与膦酰氯的偶联反应成功制备了膦酸酯键，且未破坏肽键。作为最终产物的游离氨基膦肽在ODS柱上显示出单峰，并且组分氨基酸的比例合理。这里采用的反应系列可能可用作制备膦酸肽的一般程序。
• Peptide, process for preparation thereof and use thereof
  申请人：Fujisawa Pharmaceutical Company, Ltd.

  公开号：US04725582A1

  公开（公告）日：1988-02-16

  The invention concerns peptides, having the pharmaceutical property of enhancing the immune response, having the structure: ##STR1## wherein R.sup.1 is alkanoyl, R.sub.b.sup.1 is hydrogen, methyl, isopropyl, hydroxymethyl, protected hydroxymethyl or benzyl, R.sup.2 is hydrogen, carboxy, protected carboxy or a group of the formula: ##STR2## wherein R.sub.a.sup.2 is mono- or di-carboxy (or protected carboxy) lower alkyl or ar(carboxy or protected carboxy) lower alkyl whose aryl moiety is substituted by hydroxy or not substituted, R.sub.b.sup.2 is hydrogen or lower alkyl, R.sup.p is hydrogen, carboxy or protected carboxy, R.sup.q is carboxy, protected carboxy or a group of the formula ##STR3## wherein R.sub.a.sup.2 and R.sub.b.sup.2 are each as defined above, R.sup.r is hydrogen or amino protective group, m is an integer 1 to 3, and n is an integer 1.

  本发明涉及一种具有增强免疫反应药物性质的肽，其结构为：##STR1## 其中，R.sup.1是脂肪酰基，R.sub.b.sup.1是氢、甲基、异丙基、羟甲基、保护羟甲基或苄基，R.sup.2是氢、羧基、保护羧基或式：##STR2## 其中，R.sub.a.sup.2是单或双羧基（或保护羧基）较低烷基或芳（羧基或保护羧基）较低烷基，其芳基部分被羟基取代或未取代，R.sub.b.sup.2是氢或较低烷基，R.sup.p是氢、羧基或保护羧基，R.sup.q是羧基、保护羧基或式：##STR3## 其中，R.sub.a.sup.2和R.sub.b.sup.2的含义与上述相同，R.sup.r是氢或氨基保护基，m是1至3的整数，n是1。
• Carbonic acid esters, and the preparation thereof and their use
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04010178A1

  公开（公告）日：1977-03-01

  Carbonic acid esters of the formula substituent(s) substituents(s) R'.sub.1 OCOOR'.sub.2 wherein R'.sub.1 is lower alkyl which may have substituent)s) selected from the group of halogen, lower alkoxy and aryloxy, or ar(lower)-alkyl which may have substituents)s) selected from the group of lower alkoxy, halogen, nitro and cyano, and R'.sub.2 is benzotriazolyl which may have halogen; or a group represented by the formula: ##STR1## wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl; provided that when R'.sub.2 is a group represented by the formula: ##STR2## wherein Y' and Z' are each cyano, nitro, carbamoyl or esterified carboxy, R'.sub.1 is ar(lower) alkyl having substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano. A process for the protection of amino and/or imino groups in compounds containing them by reacting them with the aforementioned esters is also disclosed.

  化学式为R'.sub.1 OCOOR'.sub.2，其中R'.sub.1为低级烷基，可以具有取自卤素、低级烷氧基和芳基氧基的取代基，或为芳基(低级)-烷基，可以具有取自低级烷氧基、卤素、硝基和氰基的取代基；R'.sub.2为苯并三唑基，可以具有卤素；或为公式所示的基团：##STR1## 其中Y'和Z'均为氰基、硝基、氨基甲酰基、酯化羧基、低级烷酰基、芳酰基或二取代氨基甲酰基；但当R'.sub.2为公式所示的基团：##STR2## 其中Y'和Z'均为氰基、硝基、氨基甲酰基或酯化羧基时，R'.sub.1为芳基(低级)烷基，具有取自低级烷氧基、卤素、硝基和氰基的取代基。还公开了一种通过与上述酯反应来保护含有氨基和/或亚氨基基团的化合物的方法。
• Oxime carbonates
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04014915A1

  公开（公告）日：1977-03-29

  Novel carbonic acid esters are disclosed which are useful in a process for introducing esterified carboxy-type protective groups on amino and/or imino groups in amino and/or imino group - containing compounds for the temporary protection of said amino and/or imino groups. Additionally, processes for preparing said esters are also disclosed.

  本发明揭示了一种新型碳酸酯，其可用于在氨基和/或亚氨基含有化合物中引入酯化羧基型保护基的过程中，对所述氨基和/或亚氨基进行临时保护。此外，本发明还揭示了制备所述酯的过程。