(R)-2-N-tert-butoxycarbonylamino-2-phenylethanenitrile

• 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: (R)-2-N-tert-butoxycarbonylamino-2-phenylethanenitrile
• 英文别名: (R)-2-N-tert-butoxycabonylamino-2-phenylethanenitrile；tert-butyl (R)-(cyano(phenyl)methyl)carbamate；tert-butyl (cyano(phenyl)methyl)carbamate；(R)-2-tert-butyloxycarbonylamino-2-phenylacetonitrile；(R)-(Cyano-phenyl-methyl)-carbamic acid tert-butyl ester；tert-butyl N-[(R)-cyano(phenyl)methyl]carbamate
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: UWMFDFGRVUUNOU-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-N-tert-butoxycarbonylamino-2-phenylethanenitrile 在 盐酸 、 水 作用下， 以 水 为溶剂， 反应 3.0h， 生成 左旋苯甘氨酸
  参考文献：
  名称：

  Enantioselective Hydrocyanation of N-Protected Aldimines

  摘要：

  Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly](2)[(S)-binap]/C6H5OLi system or a bimetallic complex [Li{Ru[(S)-phgly](2)[(S)-binap]}]Cl affords the amino nitriles in 92-99% ee. The reaction is carried out in tert-C4H9OCH3 with a substrate-to-catalyst molar ratio in the range of 500-5000 at -20 to 0 degrees C. Primary, secondary, and tertiary alkyl imines as well as the aryl and heteroaryl substrates are smoothly cyanated to produce the desired products in high yield.

  DOI：

  10.1021/ol203408w
• 作为产物：
  描述：

  (R)-(-)-2-(tert-butoxycarbonylamino)-2-phenylacetamide 在 三氟甲磺酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.38h， 以84%的产率得到(R)-2-N-tert-butoxycarbonylamino-2-phenylethanenitrile
  参考文献：
  名称：

  A Practical Method for the Preparation of Nitriles from Primary Amides Under Non-Acidic Conditions

  摘要：

  为了建立一种温和的将伯酰胺转化为腈的方法，采用了各种羧酰胺与三氟甲磺酸酐和三乙胺（作为脱水剂）处理，从而以84-95%的产率得到了所需的腈类化合物。

  DOI：

  10.1055/s-1999-3695

文献信息

• A convenient new procedure for converting primary amides into nitriles
  作者：Chun-Wei Kuo、Jia-Liang Zhu、Jen-Dar Wu、Cheng-Ming Chu、Ching-Fa Yao、Kak-Shan Shia

  DOI：10.1039/b614061k

  日期：——

  An operationally simple and high-yielding procedure has been developed for the conversion of primary amides to the corresponding nitriles, using ethyl dichlorophosphate/DBU as the mild dehydrating agent.

  使用二氯磷酸乙酯/ DBU作为温和的脱水剂，已开发出一种操作简单且产率高的程序，可将伯酰胺转化为相应的腈。
• Preparation of nitriles from primary amides under Swern oxidation conditions
  作者：Noriyuki Nakajima、Makoto Ubukata

  DOI：10.1016/s0040-4039(97)00316-x

  日期：1997.3

  In order to establish a mild conversion method of primary amides to nitriles, various types of carboxamides were treated under Swern oxidation conditions, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain desired nitriles in 75–96% yields.

  为了建立伯酰胺向腈的温和转化方法，在Swern氧化条件下处理了各种类型的羧酰胺（COCl）2 -DMSO和Et 3 N作为脱水剂，以75-96％的收率获得了所需的腈。 。
• Nitrile derivatives that inhibit cathepsin K
  申请人：——

  公开号：US20010008901A1

  公开（公告）日：2001-07-19

  Compounds of the formula: 1 wherein R 1 to R 7 and Y are as defined in the specification, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof, are useful for treating diseases associated with cystein proteases, such as osteoporosis, osteoarthritis, rheumatoid arthritis, tumor metastasis, glomerulonephritis, atherosclerosis, myocardial infarction, angina pectoris, instable angina pectoris, stroke, plaque rupture, transient ischemic attacks, amaurosis fugax, peripheral arterial occlusive disease, restenosis after angioplasty and stent placement, abdominal aortic aneurysm formation, inflammation, autoimmune disease, malaria, ocular fundus tissue cytopathy and respiratory disease.

  该公式化合物：其中R1到R7和Y如规范中定义，并且其药用盐和/或药用酯是用于治疗与半胱氨酸蛋白酶相关的疾病，如骨质疏松症、骨关节炎、类风湿性关节炎、肿瘤转移、肾小球肾炎、动脉粥样硬化、心肌梗死、心绞痛、不稳定性心绞痛、中风、斑块破裂、短暂性缺血性发作、瞬间性视网膜动脉阻塞、外周动脉闭塞性疾病、血管成形术和支架植入术后再狭窄、腹主动脉瘤形成、炎症、自身免疫疾病、疟疾、眼底组织细胞病变和呼吸道疾病的有用化合物。
• Asymmetric Strecker Reactions Catalyzed by Thiourea Phosphonium and Ammonium Salts
  作者：Hongyu Wang、Kaiye Wang、Yanfei Ren、Na Li、Bo Tang、Gang Zhao

  DOI：10.1002/adsc.201700029

  日期：2017.6.6

  The application of asymmetric phase‐transfer catalysis to the Strecker reaction of ketimines was realized utilizing bifunctional thiourea‐phosphonium salts. The asymmetric Strecker reaction of aldimines was also realized utilizing quaternary ammonium salts derived from amino acids.

  利用双功能硫脲-phosph盐实现了不对称相转移催化在酮亚胺的Strecker反应中的应用。还利用衍生自氨基酸的季铵盐实现了亚胺的不对称Strecker反应。
• A Simple Method for the Synthesis of Nitriles from Primary Amides Under Neutral Conditions
  作者：D. Subhas Bose、K. Sugnana Sunder

  DOI：10.1080/00397919908085896

  日期：1999.12.1

  Abstract 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) is a very useful reagent for the preparation of nitriles in good yields under neutral conditions.

  摘要 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐 (EDCI) 是一种非常有用的试剂，可在中性条件下以良好的收率制备腈。