5-(Triphenyl-λ⁵-phosphanylidene)-pentanenitrile | 117834-01-2

• 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: 5-(Triphenyl-λ⁵-phosphanylidene)-pentanenitrile
• 英文别名: 5-(Triphenyl-lambda5-phosphanylidene)pentanenitrile；5-(triphenyl-λ5-phosphanylidene)pentanenitrile
• CAS: 117834-01-2
• 化学式: C₂₃H₂₂NP
• 分子量: 343.408
• InChiKey: UJQANVWIUKNDOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde 、 5-(Triphenyl-λ⁵-phosphanylidene)-pentanenitrile 以 四氢呋喃 、 正己烷 为溶剂， 以78%的产率得到(Z)-(R)-N-Cbz-2,2-dimethyl-4-(5-cyano-1-pentenyl)oxazolidine
  参考文献：
  名称：

  Synthesis of chiral vinylglycines

  摘要：

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.

  DOI：

  10.1021/jo00013a023
• 作为产物：
  描述：

  5-溴戊腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 1.5h， 生成 5-(Triphenyl-λ⁵-phosphanylidene)-pentanenitrile
  参考文献：
  名称：

  Synthesis of chiral vinylglycines

  摘要：

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.

  DOI：

  10.1021/jo00013a023

文献信息

• [EN] NOVEL CYCLOSPORIN DERIVATIVES AND USES THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS DE CYCLOSPORINE ET LEURS UTILISATIONS
  申请人：S&T GLOBAL INC

  公开号：WO2017200984A1

  公开（公告）日：2017-11-23

  A compound of the Formula (I) is disclosed: (I) or pharmaceutically acceptable salt thereof, wherein the symbols are as defined in the specification. Also described are a pharmaceutical composition comprising the same and a method for treating or preventing viral infections, inflammation, dry eye, central nervous disorders, cardiovascular diseases, cancer, obesity, diabetes, muscular dystrophy, lung, and liver, and kindey diseases, and hair loss using the same.

  公开了化合物的公式（I）：（I）或其药学上可接受的盐，其中符号如规范中定义。还描述了包含相同化合物的药物组合物，以及使用该药物组合物治疗或预防病毒感染、炎症、干眼症、中枢神经障碍、心血管疾病、癌症、肥胖症、糖尿病、肌肉萎缩症、肺部和肝脏疾病、肾脏疾病和脱发的方法。
• Leukotriene receptor antagonists. 4. Synthesis and leukotriene D4/E4 receptor antagonist activity of 4-(alkyl)acetophenone derivatives
  作者：D. Mark Gapinski、Carlos R. Roman、Lynn E. Rinkema、Jerome H. Fleisch

  DOI：10.1021/jm00396a027

  日期：1988.1

  Analogues of the leukotriene D4/E4 receptor antagonist LY171883 (1a) were synthesized in which the tetrazole was linked to the hydroxyacetophenone moiety by an all-methylene carbon chain. A key step in the synthesis involved a Wittig olefin-forming reaction between 3-methoxy-2-propylbenzaldehyde and the ylide derived from (4-carboxybutyl)triphenylphosphonium bromide to form the desired carbon chain

  合成了白三烯D4 / E4受体拮抗剂LY171883（1a）的类似物，其中四唑通过全亚甲基碳链连接到羟基苯乙酮部分。合成中的关键步骤涉及3-甲氧基-2-丙基苯甲醛与衍生自（4-羧基丁基）三苯基溴化的内鎓盐之间形成Wittig烯烃的反应，以形成所需的碳链。使用区域选择性的弗里斯重排来形成邻羟基苯乙酮。将四唑与苯乙酮被四个和五个亚甲基隔开的化合物与相应的衍生物进行了比较，在该衍生物中，氧原子将四唑链连接到芳环上，具有拮抗LTD4-或LTE4诱导的分离物收缩的能力。豚鼠回肠。与1a相比，“ carba” 类似物7a显示出几乎相同的LTD4拮抗剂活性。这两种化合物的LTE4拮抗剂活性也相同。在较短的链系列中，“ carba”类似物7b显示出增强的LTD4拮抗剂活性，而LTE4拮抗剂活性则高出约10倍。这些结果表明，与豚鼠回肠中的LTD4或LTE4受体位点缔合时，对位于1a和1b乙酰基的氧原子不是很重要。
• Enantiospecific synthesis of D-α, ω-diaminoalkanoic acids
  作者：Pierre L. Beaulieu、Peter W. Schiller

  DOI：10.1016/s0040-4039(00)87823-5

  日期：——

  An enantiospecific synthesis of D-Nω-Boc-α, ω-diaminoalkanoic acids starting from L-serine is described.

  DN的映体特异性合成ω -Boc-α，从L-丝氨酸开始ω-diaminoalkanoic酸进行说明。
• A Facile Aldol-Isomerization Route to 3-Alkyldihydropyridinone with a Chiral Azocine Ring
  作者：Masako Nakagawa、Yasuhiro Torisawa、Than Soe、Chiaki Katoh、Yumiko Motohashi、Atsushi Nishida、Tohru Hino

  DOI：10.3987/com-97-s(n)88

  日期：——
• BEAULIEU, PIERRE L.;SCHILLER, PETER W., TETRAHEDRON LETT., 29,(1988) N 17, 2019-2022
  作者：BEAULIEU, PIERRE L.、SCHILLER, PETER W.

  DOI：——

  日期：——