4-t-butylazetidin-2-one | 97033-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4-t-butylazetidin-2-one
• 英文别名: 4(S)-tert-butylazetidine-2-one；4-Tert-butylazetidin-2-one
• CAS: 97033-11-9
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: HNRJYXLAARIKIU-UHFFFAOYSA-N

物化性质

• 沸点：
  240.1±9.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(4-methoxybenzyloamino)-3,3-dimethylbutyronitrile 在 ammonium cerium(IV) nitrate 、 potassium tert-butylate 、 氨 、 sodium 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 3.5h， 生成 4-t-butylazetidin-2-one
  参考文献：
  名称：

  Shirai, Masashi; Nishiwaki, Tarozaemon, Journal of Chemical Research, Miniprint, 1990, # 9, p. 2018 - 2031

  摘要：

  DOI：

文献信息

• Azetidinone derivatives for the treatment of HCMV infections
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US06242439B1

  公开（公告）日：2001-06-05

  A compound of formula I wherein R1 is hydrogen, methyl, ethyl, methoxy or methylthio; R2 and R3 each independently is hydrogen or lower alkyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy or benzyloxy; R5 is lower alkyl, lower cycloalkyl, (CH2)mC(O)OR6 wherein m is the integer 1 or 2 and R6 is lower alkyl, phenyl optionally substituted; optionally Het or Het(lower alkyl); or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with C(O)O-benzyl or with phenyl optionally substituted with C(O)OR7 wherein R7 is lower alkyl or (lower alkyl)phenyl; and Z is lower alkyl or optionally substituted phenyl or Het; with the proviso that when Z is (CH2)p-(Het), then R2 and R3 each is hydrogen; or a therapeutically acceptable acid addition salt thereof which compound is useful in the treatment of HCMV infections.

  式I的化合物中，其中R1为氢、甲基、乙基、甲氧基或甲硫基；R2和R3各自独立地为氢或较低的烷基；R4为氢、较低的烷基、甲氧基、乙氧基或苄氧基；R5为较低的烷基、较低的环烷基、(CH2)mC(O)OR6，其中m是整数1或2，R6为较低的烷基、苯基可选择地取代；可选择地为Het或Het(较低的烷基)；或者R4和R5与它们连接的氮原子一起形成一个含氮环，该环可选择地取代为C(O)O-苄基或苯基，该苯基可选择地取代为C(O)OR7，其中R7为较低的烷基或(较低的烷基)苯基；Z为较低的烷基或可选择地取代的苯基或Het；但是当Z为(CH2)p-(Het)时，那么R2和R3各自为氢；或其治疗上可接受的酸盐，该化合物在HCMV感染的治疗中有用。
• Synthesis of 4-substituted 2-azetidinones
  作者：Duy H. Hua、Akhilkumar Verma

  DOI：10.1016/s0040-4039(00)89144-3

  日期：1985.1

  4-Substituted 2-azetidinones were obtained in excellent yields from the reaction of various cuprates with 4-acetoxy-2-azetidinone.

  从各种铜酸盐与4-乙酰氧基-2-氮杂环丁酮的反应中，以优异的产率获得了4-取代的2-氮杂环丁酮。
• SMALL MOLECULES THAT COVALENTLY MODIFY TRANSTHYRETIN
  申请人：Kelly Jeffery W.

  公开号：US20120270938A1

  公开（公告）日：2012-10-25

  A family of covalent kinetic stabilizer compounds that selectively and covalently react with the prominent plasma protein transthyretin in preference to more than 4000 other human plasma proteins is disclosed. A contemplated compound corresponds in structure to Formula I, below, where the various substituents are defined within, and reacts chemoselectively with one or two of four Lys-15 ε-amino groups within the transthyretin tetramer. The crystal structure confirms the binding orientation of the compound substructure and the conjugating amide bond. A covalent transthyretin kinetic stabilizer exhibits superior amyloid inhibition potency, compared to a non-covalent counterpart, and inhibits cytotoxicity associated with amyloidogenesis.

  本文介绍了一类共价动力稳定剂化合物家族，它们选择性地、共价地与突出的血浆蛋白转甲状腺素结合，而不是其他4000多种人类血浆蛋白。一种可考虑的化合物对应于以下的结构式I，其中各取代基在内部定义，并与转甲状腺素四聚体中的一个或两个Lys-15 ε-氨基基团发生化学选择性反应。晶体结构证实了化合物亚结构和结合酰胺键的结合方向。与非共价对应物相比，共价转甲状腺素动力稳定剂表现出优越的淀粉样抑制效能，并抑制与淀粉样生成相关的细胞毒性。
• Small Molecules That Covalently Modify Transthyretin
  申请人：Kelly Jeffery W.

  公开号：US20140336254A1

  公开（公告）日：2014-11-13

  A family of covalent kinetic stabilizer compounds that selectively and covalently react with the prominent plasma protein transthyretin in preference to more than 4000 other human plasma proteins is disclosed. A contemplated compound corresponds in structure to Formula I, below, where the various substituents are defined within, and reacts chemoselectively with one or two of four Lys-15 ε-amino groups within the transthyretin tetramer. The crystal structure confirms the binding orientation of the compound substructure and the conjugating amide bond. A covalent transthyretin kinetic stabilizer exhibits superior amyloid inhibition potency, compared to a non-covalent counterpart, and inhibits cytotoxicity associated with amyloidogenesis.

  本发明揭示了一种共价动力稳定剂化合物家族，它们选择性地和共价地与显著的血浆蛋白转甲状腺素反应，而不是其他4000多种人类血浆蛋白。考虑到的化合物对应于以下公式I的结构，其中各种取代基在内部定义，并与转甲状腺素四聚体内的四个Lys-15 ε-氨基基团之一或两个发生化学选择性反应。晶体结构证实了化合物亚结构和结合酰胺键的结合方向。与非共价对应物相比，共价转甲状腺素动力稳定剂表现出优越的淀粉样抑制效力，并抑制与淀粉样生成相关的细胞毒性。
• SHIRAI, MASASHI;NISHIWAKI, TAROZAEMON, J. CHEM. RES. (S),(1990) N, C. 270
  作者：SHIRAI, MASASHI、NISHIWAKI, TAROZAEMON

  DOI：——

  日期：——