4-(4-Methoxy-phenoxy)-butan-2-one | 32352-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-Methoxy-phenoxy)-butan-2-one
• 英文别名: 4-(4-Methoxyphenoxy)butan-2-one
• CAS: 32352-97-9
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: COQFRNATNHCYQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4-(4-Methoxy-phenoxy)-butan-2-one 、 (1S,2S)-N-(trifluoroacetyl)norpseudoephedrine trimethylsilyl ether 、 烯丙基三甲基硅烷 在 三氟甲磺酸 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,2,2-Trifluoro-N-((1S,2S)-2-{(R)-1-[2-(4-methoxy-phenoxy)-ethyl]-1-methyl-but-3-enyloxy}-1-methyl-2-phenyl-ethyl)-acetamide 、 2,2,2-Trifluoro-N-((1S,2S)-2-{(S)-1-[2-(4-methoxy-phenoxy)-ethyl]-1-methyl-but-3-enyloxy}-1-methyl-2-phenyl-ethyl)-acetamide
  参考文献：
  名称：

  Synthesis of Enantiopure Homoallylic Alcohols

  摘要：

  A highly selective asymmetric domino allylation of aliphatic ketones is described. When methyl ketones 1a-g, the chiral trimethylsilyl ether 2, and allylsilane 3 react in the presence of catalytic amounts of trifluoromethanesulfonic acid, the homoallylic ethers 4a-g are produced with up to 24:1 diastereoselectivity and 89% yield. Cleavage of the obtained tertiary homoallylic ethers C using lithium or sodium in liquid ammonia gives the homoallytic alcohols 5 in 75 to 95% yield and up to 92% ee. Even ethyl methyl ketone 1a, the most difficult example, showed a stereoselectivity of 9:1 at -78 degrees C and 24:1 at -109 degrees C. In addition, the allylation of protected hydroxyalkyl methyl ketones 7a-j was investigated to give the corresponding homoallylic ethers 8a-j with a diastereoselectivity of up to >24:1 and 98% yield. In contrast, ethyl alkyl ketones 1h-j have a low selectivity.

  DOI：

  10.1002/(sici)1521-3765(19980904)4:9<1862::aid-chem1862>3.0.co;2-c

文献信息

• Compositions and methods for treating cardiovascular disease
  申请人：Genentech, Inc.

  公开号：US11034725B2

  公开（公告）日：2021-06-15

  The invention provides PCSK9 inhibitors, compositions comprising the PCSK9 inhibitors, and methods of identifying and using the PCSK9 inhibitors.

  本发明提供了 PCSK9 抑制剂、包含 PCSK9 抑制剂的组合物以及鉴定和使用 PCSK9 抑制剂的方法。
• MPASSI, MICHEL;GUILLAUMET, GERALD;COUDERT, GERHARD;TISSIER, MADELEINE;JUI+, CAN. J. CHEM., 67,(1989) N, C. 1132-1138
  作者：MPASSI, MICHEL、GUILLAUMET, GERALD、COUDERT, GERHARD、TISSIER, MADELEINE、JUI+

  DOI：——

  日期：——
• GLUCOSYLCERAMIDE SYNTHASE INHIBITION FOR THE TREATMENT OF COLLAPSING GLOMERULOPATHY AND OTHER GLOMERULAR DISEASE
  申请人：Genzyme Corporation

  公开号：EP2320886B1

  公开（公告）日：2017-06-28
• COMPOSITIONS AND METHODS FOR TREATING CARDIOVASCULAR DISEASE
  申请人：Genentech, Inc.

  公开号：US20200283478A1

  公开（公告）日：2020-09-10

  The invention provides PCSK9 inhibitors, compositions comprising the PCSK9 inhibitors, and methods of identifying and using the PCSK9 inhibitors.
• Synthesis of Enantiopure Homoallylic Alcohols
  作者：Lutz F. Tietze、Kai Schiemann、Christoph Wegner、Christian Wulff

  DOI：10.1002/(sici)1521-3765(19980904)4:9<1862::aid-chem1862>3.0.co;2-c

  日期：1998.9.4

  A highly selective asymmetric domino allylation of aliphatic ketones is described. When methyl ketones 1a-g, the chiral trimethylsilyl ether 2, and allylsilane 3 react in the presence of catalytic amounts of trifluoromethanesulfonic acid, the homoallylic ethers 4a-g are produced with up to 24:1 diastereoselectivity and 89% yield. Cleavage of the obtained tertiary homoallylic ethers C using lithium or sodium in liquid ammonia gives the homoallytic alcohols 5 in 75 to 95% yield and up to 92% ee. Even ethyl methyl ketone 1a, the most difficult example, showed a stereoselectivity of 9:1 at -78 degrees C and 24:1 at -109 degrees C. In addition, the allylation of protected hydroxyalkyl methyl ketones 7a-j was investigated to give the corresponding homoallylic ethers 8a-j with a diastereoselectivity of up to >24:1 and 98% yield. In contrast, ethyl alkyl ketones 1h-j have a low selectivity.