3,5-dibenzyloxylbenzoyl chloride | 28917-44-4

• 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: 3,5-dibenzyloxylbenzoyl chloride
• 英文别名: 3,5-dibenzyloxybenzoyl chloride；3,5-Bis(benzyloxy)benzoyl chloride；3,5-bis(phenylmethoxy)benzoyl chloride
• CAS: 28917-44-4
• 化学式: C₂₁H₁₇ClO₃
• 分子量: 352.817
• InChiKey: GWIBCCZNAYLLCD-UHFFFAOYSA-N

物化性质

• 沸点：
  511.6±40.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dibenzyloxylbenzoyl chloride 在 N-乙基吗啉 、 吡啶 、 1,3-bis-(1-adamantyl)imidazolinium tetrafluoroborate 、 二甲基硫 、 三氟化硼乙醚 、 palladium diacetate 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 对二甲苯 为溶剂， 反应 27.0h， 生成 (E)-4-(3,5-dihydroxystyryl)phenyl pivalate
  参考文献：
  名称：

  A new synthesis of 4′-resveratrol esters and evaluation of the potential for anti-depressant activity

  摘要：

  The 4'-ester analog of the disease preventative resveratrol 1 (RV), 4'-acetyl-RV 2 along with 4'-pivaloate 13 and benzoate 14 RV were synthesized. The previously developed palladium catalyzed decarbonylative Heck coupling was used to assemble the stilbene core together with 3,5-dibenzyl protected phenol intermediates that allowed for efficient coupling and deprotection using boron trifiuoride etherate. Studies with Long-Evans rats were performed to establish safety, toxicity, and behavioral parameters. In addition, the Porsalt forced-swim test was used to demonstrate anti-depressant activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.046
• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 氯化亚砜 、 硫酸 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 3,5-dibenzyloxylbenzoyl chloride
  参考文献：
  名称：

  A new synthesis of 4′-resveratrol esters and evaluation of the potential for anti-depressant activity

  摘要：

  The 4'-ester analog of the disease preventative resveratrol 1 (RV), 4'-acetyl-RV 2 along with 4'-pivaloate 13 and benzoate 14 RV were synthesized. The previously developed palladium catalyzed decarbonylative Heck coupling was used to assemble the stilbene core together with 3,5-dibenzyl protected phenol intermediates that allowed for efficient coupling and deprotection using boron trifiuoride etherate. Studies with Long-Evans rats were performed to establish safety, toxicity, and behavioral parameters. In addition, the Porsalt forced-swim test was used to demonstrate anti-depressant activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.046

文献信息

• Trisubstituted carbocyclic cyclophilin binding compounds and their use
  申请人：——

  公开号：US20020165275A1

  公开（公告）日：2002-11-07

  The present invention relates to novel, non-peptidic small organic compounds having an affinity for cyclophilin (CyP)-type immunophilin proteins, and to pharmaceutical compositions comprising one or more of the said compounds. The invention further relates to the uses of these compounds and compositions for binding CyP-type proteins, inhibiting their peptidyl-prolyl isomerase activity, and for research, development, and therapeutic applications in a variety of medical disorders.

  本发明涉及一种新型的非肽类小有机化合物，其具有与环肽亚精蛋白（CyP）型免疫蛋白亲和力，并且涉及包含所述化合物中的一个或多个的药物组合物。该发明还涉及这些化合物和组合物用于结合CyP型蛋白，抑制其肽基脯氨酸异构酶活性，并在各种医学疾病的研究、开发和治疗应用中的用途。
• Dicarbonyl chelates from 1-cymantrenylalkylamides with the dendrite structure: formation, photochromism, and kinetics of dark reaction with carbon monoxide
  作者：S. Kelbysheva、L. N. Telegina、O. V. Abramova、T. V. Strelkova、N. S. Ikonnikov、A. N. Rodionov、M. G. Ezernitskaya、B. V. Lokshin、N. M. Loim

  DOI：10.1007/s11172-015-1203-0

  日期：2015.11

  leads to the formation of six-membered dicarbonyl chelates with the Mn—O bond which are stable in solutions. The chelates in the reversed dark reaction with carbon monoxide give the starting tricarbonyl complexes. The formation of the chelates and their dark reaction are accompanied by the reversible change of color by the compounds. The rate determining step of the thermal reaction of chelates with

  具有氨基甲基和 1-氨基乙基花环烃的树枝状结构的羧酰胺的光解导致形成六元二羰基螯合物，其具有在溶液中稳定的 Mn-O 键。与一氧化碳的反向暗反应中的螯合物得到起始的三羰基配合物。螯合物的形成和它们的暗反应伴随着化合物的可逆颜色变化。螯合物与 CO 热反应的速率决定步骤是螯合开环，配体取代通过 SN1 机制。证明了在许多伞花烃衍生物中进行无溶剂光诱导配体交换反应的可能性。
• Synthesis and characterisation of water-soluble poly(aryl ether) dendrimers for encapsulation of biomimetic active site analogues †
  作者：Michael J. Hannon、Paul C. Mayers、Paul C. Taylor

  DOI：10.1039/b002026p

  日期：——

  Synthetic strategies to incorporate active site analogues of metalloenzymes at the core of water-soluble dendritic structures are explored. Synthesis of water-soluble aryl ether dendrimers containing tripyridyl metal-binding sites is successful when a convergent, but not a divergent, strategy is employed.

  探讨了将金属酶的活性位点类似物融入水溶性树状结构核心的合成策略。当采用聚合而非发散策略时，成功合成了包含三吡啶金属结合位点的水溶性芳基醚树状聚合物。
• Synthesis of Alternating Polystyrene/Poly(ethyleneoxide) Branched Polymacromonomers
  作者：Valadoula Deimede、Joannis K. Kallitsis

  DOI：10.1002/1521-3765(20020118)8:2<467::aid-chem467>3.0.co;2-1

  日期：2002.1.18

  5-bis(benzyloxy)benzoyl chloride. Polycondensation of the alpha-dicarboxy PS with the alpha-dihydroxy PEO in solution or in bulk resulted in alternating PS/PEO polymacromonomers, which were effectively purified from the unreacted macromonomers and characterized by using 1H NMR, GPC, thermal analysis, and optical microscopy. Light-scattering measurements in organic solvents like THF or dioxane have shown that

  通过α-二羧基官能化的聚苯乙烯和α-二羟基官能化的聚环氧乙烷的缩聚反应，获得了新设计的PS / PEO交替支化的大分子单体。4- [3,5-双（甲氧基羰基）苯氧基甲基]苄基溴被用作原子转移自由基聚合（ATRP）引发剂，用于合成α-二羧基官能化的聚苯乙烯。这些大分子单体具有低的多分散性，分子量在7000至100,000之间，这已通过凝胶渗透色谱法（GPC）和1H NMR证实。通过用3,5-双（苄氧基）苯甲酰氯处理单官能化的PEO，合成了α-二羟基官能化的聚环氧乙烷（PEO）。溶液或本体中α-二羧基PS与α-二羟基PEO的缩聚导致交替出现PS / PEO聚大分子单体，从未反应的大分子单体中有效纯化得到的化合物，并通过1 H NMR，GPC，热分析和光学显微镜进行表征。在有机溶剂（如THF或二恶烷）中进行的光散射测量表明，这些聚大分子单体形成稳定的胶束。
• Solid-Phase Synthesis Using (Allyloxy)carbonyl(Alloc) Chemistry of a Putative Heptapeptide Intermediate in Vancomycin Biosynthesis Containing m-Chloro-3-hydroxytyrosine
  作者：Ernst Freund、Francesca Vitali、Anthony Linden、John A. Robinson

  DOI：10.1002/1522-2675(20000906)83:9<2572::aid-hlca2572>3.0.co;2-x

  日期：2000.9.6

  convenient method for the solid-phase synthesis of putative linear heptapeptide intermediates in vancomycin biosynthesis is described, in particular, the heptapeptide D-Leu-Cyt-L-Asn-Hpg-Hpg-Cyt′-Dhpg (Cyt=(2R,3R)-m-chloro-3-hydroxytyrosine, Hpg=(R)-2-(p-hydroxyphenyl)glycine, Cyt′=(2S,3R)-m-chloro-3-hydroxytyrosine and Dhpg=(S)-2-(3,5-dihydroxyphenyl)glycine). The synthesis was performed on chlorotrityl resin

  描述了一种在万古霉素生物合成中固相合成假定的线性七肽中间体的简便方法，特别是七肽 D-Leu-Cyt-L-Asn-Hpg-Hpg-Cyt'-Dhpg (Cyt=(2R,3R )-m-chloro-3-hydroxytyrosine, Hpg=(R)-2-(p-hydroxyphenyl)glycine, Cyt'=(2S,3R)-m-chloro-3-hydroxytyrosine and Dhpg=(S)-2- (3,5-二羟基苯基)甘氨酸)。该合成是在氯三苯甲基树脂上进行的，并在肽链组装过程中使用（烯丙氧基）羰基保护基团进行临时 N（α）保护。