(4S,5R)-4-methyl-3-(4-methylpentanoyl)-5-phenyl-oxazolidin-2-one | 168540-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-4-methyl-3-(4-methylpentanoyl)-5-phenyl-oxazolidin-2-one
• 英文别名: (4S,5R)-3-(4-methylpentanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on；(4S,5R)-3-(1-oxo-4-methylpentyl)-4-methyl-5-phenyl-2-oxazolidinone；(4S,5R)-4-methyl-3-(4-methylpentanoyl)-5-phenyl-1,3-oxazolidin-2-one
• CAS: 168540-62-3
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: YMFUBEFDXJOXRZ-WFASDCNBSA-N

物化性质

• 沸点：
  423.0±34.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-methyl-3-(4-methylpentanoyl)-5-phenyl-oxazolidin-2-one 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 N-羟基-7-氮杂苯并三氮唑 、 Hoveyda-Grubbs catalyst second generation 、 tetra-n-propylammonium perruthenate. 、 双氧水 、 三甲基铝 、 四氯化钛 、 N-甲基吗啉氧化物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 94.58h， 生成 (+)-丁苯那嗪
  参考文献：
  名称：

  A Ring-Closing Metathesis-Based Approach to the Synthesis of (+)-Tetrabenazine

  摘要：

  A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-alpha-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.

  DOI：

  10.1021/ol301612q
• 作为产物：
  描述：

  去甲麻黄碱 在 三甲基乙酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 (4S,5R)-4-methyl-3-(4-methylpentanoyl)-5-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  A Ring-Closing Metathesis-Based Approach to the Synthesis of (+)-Tetrabenazine

  摘要：

  A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-alpha-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.

  DOI：

  10.1021/ol301612q

文献信息

• A Synthetic Library of Cell-Permeable Molecules
  作者：Kazunori Koide、Joshua M. Finkelstein、Zachary Ball、Gregory L. Verdine

  DOI：10.1021/ja0023377

  日期：2001.1.1

  FK506-binding protein (AP1867) attached to 320 substituted tetrahydrooxazepines (THOXs). The THOX components were generated by a combination of liquid- and solid-phase procedures employing sequential Mitsonobu displacements to join two structurally diversified olefin-containing monomers, followed by ruthenium-mediated olefin metathesis to effect closure of the seven-membered ring. The 320 resin-bound THOX ligands

  已证明诱导或稳定大分子结合的小分子是多种生物过程的有用效应物。迄今为止，这种二聚化化学诱导剂的所有例子都涉及到充分表征的蛋白质的已知配体。这种方法的通用性可以通过发现靶向已知大分子的异二聚化剂或在没有预先确定的大分子靶点的筛选中产生新的生物反应的异源二聚化剂来扩大。为此，我们报告了合成异二聚体的多元化文库的构建，该文库由以 FK506 结合蛋白 (AP1867) 为目标的不变配体组成，该蛋白与 320 取代的四氢氧氮杂 (THOX) 相连。THOX 组分是通过液相和固相程序的组合产生的，采用连续的 Mitsonobu 置换来加入两种结构多样化的含烯烃单体，然后是钌介导的烯烃复分解，以实现七元环的闭合。320 个树脂结合的 THOX 配体与 AP1867 平行偶联，产物从树脂中释放出来，以足够的产率和纯度产生候选异二聚体，可直接用于生物测试。测试了 25 种候选异源二聚体的代表性小组通过人纤
• Sulfoximine and suldodiimine matrix metalloproteinase inhibitors
  申请人：Florida State University

  公开号：US05470834A1

  公开（公告）日：1995-11-28

  Novel sulfoximine and sulfodiimine matrix metalloproteinase inhibitors of the formula, ##STR1## wherein: R.sup.1 is selected from the group consisting of lower-alkyl, hydroxy lower-alkyl, amino lower-alkyl, carbamoyl lower-alkyl, lower-alkyl carbonyl, lower-alkyoxyalkyl, aralkyl and heteroaralkyl; X is NH or O; R.sup.2 is selected from the group consisting of hydrogen, lower-alkyl and aralkyl; R.sup.3 is selected from the group consisting of hydrogen, lower-alkyl, amino lower-alkyl, guanyl lower-alkyl, aralkyl and heteroaralkyl; and R.sup.4 is selected from the group consisting of lower alkyl, aralkyl and --CH(R.sup.5)--C(O)NH.sub.2, wherein R.sup.5 is selected from the group consisting of hydrogen, lower-alkyl, amino lower-alkyl, guanyl lower-alkyl, imidazoylalkyl, hydroxymethyl, 1-hydroxyethyl, mercapto lower-alkyl, and methylthio lower-alkyl; useful for modulating physiological functions or treating diseases and disease conditions associated with matrix metalloproteinase modulation.

  新型的磺酰亚胺和磺二亚胺基基质金属蛋白酶抑制剂的化学式为：##STR1## 其中：R1选自以下组成的群体：低碳基、羟基低碳基、氨基低碳基、氨基甲酰低碳基、低碳基酰基、低碳氧基烷基、芳基烷基和杂芳基烷基；X为NH或O；R2选自以下组成的群体：氢、低碳基和芳基烷基；R3选自以下组成的群体：氢、低碳基、氨基低碳基、鸟氨酸基低碳基、芳基烷基和杂芳基烷基；R4选自以下组成的群体：低碳基、芳基烷基和--CH(R5)--C(O)NH2，其中R5选自以下组成的群体：氢、低碳基、氨基低碳基、鸟氨酸基低碳基、咪唑基烷基、羟甲基、1-羟基乙基、巯基低碳基和甲硫基低碳基；用于调节生理功能或治疗与基质金属蛋白酶调节相关的疾病和疾病状况。
• A Modular Synthetic Approach toward Exhaustively Stereodiversified Ligand Libraries
  作者：Tiffany Malinky Gierasch、Milan Chytil、Mary T. Didiuk、Julie Y. Park、Jeffrey J. Urban、Steven P. Nolan、Gregory L. Verdine

  DOI：10.1021/ol006560k

  日期：2000.12.1

  This report describes a modular approach to the synthesis of stereodiversified natural product like libraries. Monomers 2 and 3 were coupled in parallel by silyl tethered olefin metathesis to generate all 16 stereoisomers of cis-enediols 1. All 16 stereoisomers were incorporated into chimerae having flanking peptidic segments. These chimerae exhibited a broad range of hydrophobicities, raising the possibility that stereochemical variation might be used to tune the pharmacologic properties of small molecules.
• US5470834A
  申请人：——

  公开号：US5470834A

  公开（公告）日：1995-11-28
• A Ring-Closing Metathesis-Based Approach to the Synthesis of (+)-Tetrabenazine
  作者：Manuel Johannes、Karl-Heinz Altmann

  DOI：10.1021/ol301612q

  日期：2012.7.20

  A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-alpha-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.