(4S)-3-<(2E)-3-(4-methoxyphenyl)propenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one | 154006-98-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4S)-3-<(2E)-3-(4-methoxyphenyl)propenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]-1,3-oxazolidin-2-one；(4S)-4-benzyl-3-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 154006-98-1
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: KMGXFHWBLRJLHY-KQPPXVQYSA-N

物化性质

• 沸点：
  491.9±47.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-3-<(2E)-3-(4-methoxyphenyl)propenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one 在 lithium hydroxide 、 氯化亚砜 、 manganese triacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 苯 为溶剂， 反应 18.25h， 生成 propan-2-yl (2R,3R)-3-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-2-(4-methoxyphenyl)-5-methyl-2,3-dihydrofuran-4-carboxylate
  参考文献：
  名称：

  Asymmetric Mn(III)-based radical synthesis of functionalized 2,3-dihydrofurans

  摘要：

  The oxidative radical addition of alkyl acetoacetates to p-methoxycinnamoyl oxazolidinones promoted by Mn(III) has been studied. It only gives trans-disubstituted 2,3-dihydrofurans, with d.r. ranging from 2:1 to 9:1, depending on the substituent of the chiral auxiliary. After chromatographic separation of the two diastereomers, the oxazolidinone can be removed to afford enantiopure dihydrofuranyl esters in good overall yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01729-9
• 作为产物：
  描述：

  反式-4-甲氧基肉桂酸 、 (S)-4-苄基-2-唑烷酮 在 草酰氯 、 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以2.93 g的产率得到(4S)-3-<(2E)-3-(4-methoxyphenyl)propenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  PIPERAZINE DERIVATIVE

  摘要：

  公开号：

  EP3333165B1

文献信息

• Asymmetric double aldol reaction of chiral acetyloxazolidinone
  作者：Hiroshi Furuno、Tadashi Inoue、Atsushi Abiko

  DOI：10.1016/s0040-4039(02)02021-x

  日期：2002.11

  Treatment of chiral oxazolidinone with Bu2BOTf (2.5 equiv.) and Et3N (3.0 equiv.) quantitatively produced the doubly borylated enolate, which afforded the double aldol products with high diastereoselectivity after reaction with aldehydes.

  用Bu 2 BOTf（2.5当量）和Et 3 N（3.0当量）处理手性恶唑烷酮可定量生成双硼化烯醇酸酯，与醛反应后，该双羟醛酸酯产物具有高非对映选择性。
• Piperazine derivative
  申请人：Astellas Pharma Inc.

  公开号：US10301286B2

  公开（公告）日：2019-05-28

  To provide a compound which can be used as an MC4 receptor agonist. The present inventors have investigated MC4 receptor agonists, and have found that a piperazine derivative has an action related to the agonists, thereby completing the present invention. That is, the piperazine derivative of the present invention has an MC4 receptor agonistic action, and can be used as an agent for preventing or treating bladder and/or urinary tract diseases, in particular, underactive bladder, hypotonic bladder, acontractile bladder, detrusor underactivity, neurogenic bladder, urethral relaxation failure, detrusor-external urethral sphincter dyssynergia, and voiding dysfunctions in benign prostatic hyperplasia.

  提供一种可用作 MC4 受体激动剂的化合物。 本发明者对 MC4 受体激动剂进行了研究，发现一种哌嗪衍生物具有与激动剂相关的作用，从而完成了本发明。也就是说，本发明的哌嗪衍生物具有 MC4 受体激动剂的作用，可用作预防或治疗膀胱和/或尿路疾病的药物，特别是膀胱功能减退症、本发明的哌嗪衍生物具有 MC4 受体激动作用，可用作预防或治疗膀胱和/或尿路疾病的药物，特别是低张性膀胱、收缩性膀胱、逼尿肌活动不足、神经源性膀胱、尿道松弛衰竭、逼尿肌-外尿道括约肌功能障碍以及良性前列腺增生症的排尿功能障碍。
• Rueck, Karola; Kunz, Horst, Synthesis, 1993, # 10, p. 1018 - 1028
  作者：Rueck, Karola、Kunz, Horst

  DOI：——

  日期：——
• NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (−)-cytoxazone and droxidopa
  作者：Shyla George、Srinivasarao V. Narina、Arumugam Sudalai

  DOI：10.1016/j.tetlet.2006.12.109

  日期：2007.2

  The NaIO4-mediated asymmetric bromohydroxylation of alpha,beta-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral alpha-bromo-beta-hydroxy carboxamides. Excellent yields (77-90%) and diastereoselectivities (up to 10:1) along with exclusive control over regio- as well as anti-selectivity are the main features with a good scope of substrates. The method has successfully been applied in the enantioselective syntheses of two biologically important molecules, viz (-)-cytoxazone and L-threo-DOPS (droxidopa). (c) 2007 Elsevier Ltd. All rights reserved.
• US7390826B2
  申请人：——

  公开号：US7390826B2

  公开（公告）日：2008-06-24