3-methoxybiphenyl-4-yl isothiocyanate | 1304028-65-6

• 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-methoxybiphenyl-4-yl isothiocyanate
• 英文别名: 4-(3-methoxy)biphenyl isothiocyanate；[4-phenyl-(2-methoxyphenyl)]isothiocyanate；1-Isothiocyanato-2-methoxy-4-phenylbenzene
• CAS: 1304028-65-6
• 化学式: C₁₄H₁₁NOS
• 分子量: 241.313
• InChiKey: NZMWSNIJUPSXRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxybiphenyl-4-yl isothiocyanate 、 阿奇霉素 A 在 三乙胺 作用下， 以 乙腈 为溶剂， 以41%的产率得到9a,11-O-{N'-[4-(3-methoxy)biphenyl]carbonimidoyl}-9-deoxo-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Novel 9a,11-bridged azalides: One-pot synthesis of N′-substituted 2-imino-1,3-oxazolidines condensed to an azalide aglycone

  摘要：

  An efficient one-pot method for the synthesis of novel 9a,11-bridged 15-membered 9a-aza-9-deoxo-9a-homoerythromycin A and its 6-O-methyl analogue has been developed. The novel bicyclic azalide scaffold is characterized by an N'-substituted-2-imino-1,3-oxazolidine moiety bound to a macrolactone ring between positions 9a and 11. Removal of the cladinose sugar from the starting compounds allows easy preparation of a small series of such bicyclic 3-keto and 3,6-hemiketal azalide derivatives. A mechanism for the formation of N'-substituted-2-imino-1,3-oxazolidines is discussed. Antibacterial properties of the prepared compounds were evaluated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.061

文献信息

• Novel Tandem Reaction for the Synthesis of N′-Substituted 2-Imino-1,3-oxazolidines from Vicinal (sec- or tert-)Amino Alcohol of Desosamine
  作者：Ines Vujasinović、Zorica Marušić Ištuk、Samra Kapić、Mirjana Bukvić Krajačić、Antun Hutinec、Ivica Đilović、Dubravka Matković-Čalogović、Goran Kragol

  DOI：10.1002/ejoc.201001707

  日期：2011.5

  2-imino-1, 3-oxazolidine structures. The yields of both one-pot methods are comparable to the yield of the sequential reaction. A small library of a new class of desosamine-modified 14- and 15-membered macrolides was prepared to demonstrate the variety of substituents that can be easily introduced and thus enable a huge variation of the physicochemical and hence biological properties of these new molecules

  两种一锅法，顺序和串联，用于从脱糖胺的连位（仲或叔）-氨基醇通过中间烷基-、芳基-、杂芳基制备 N'-取代的 2-亚氨基-1, 3-恶唑烷-，和杂烷基硫脲部分被描述。特别有趣的是连位叔氨基醇的新型一锅串联反应，包括脱烷基化、硫脲形成和最终环化以产生 2-亚氨基-1, 3-恶唑烷结构。两种一锅法的产率与顺序反应的产率相当。制备了一类新的脱糖胺修饰的 14 元和 15 元大环内酯类的小型文库，以证明可以轻松引入的各种取代基，从而使这些新分子的物理化学和生物学特性发生巨大变化。
• US6153634A
  申请人：——

  公开号：US6153634A

  公开（公告）日：2000-11-28
• Novel 9a,11-bridged azalides: One-pot synthesis of N′-substituted 2-imino-1,3-oxazolidines condensed to an azalide aglycone
  作者：Zorica Marušić Ištuk、Ana Čikoš、Dubravka Gembarovski、Gorjana Lazarevski、Ivica Đilović、Dubravka Matković-Čalogović、Goran Kragol

  DOI：10.1016/j.bmc.2010.10.061

  日期：2011.1

  An efficient one-pot method for the synthesis of novel 9a,11-bridged 15-membered 9a-aza-9-deoxo-9a-homoerythromycin A and its 6-O-methyl analogue has been developed. The novel bicyclic azalide scaffold is characterized by an N'-substituted-2-imino-1,3-oxazolidine moiety bound to a macrolactone ring between positions 9a and 11. Removal of the cladinose sugar from the starting compounds allows easy preparation of a small series of such bicyclic 3-keto and 3,6-hemiketal azalide derivatives. A mechanism for the formation of N'-substituted-2-imino-1,3-oxazolidines is discussed. Antibacterial properties of the prepared compounds were evaluated. (C) 2010 Elsevier Ltd. All rights reserved.