(3S,6R)-3,6-二异丙基-4-甲基-2,5-吗啉二酮 | 812788-12-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (3S,6R)-3,6-二异丙基-4-甲基-2,5-吗啉二酮
• 英文名称: (3S,6R)-3,6-diisopropyl-4-methyl-2,5-morpholinedione
• 英文别名: 1,4-perhydrooxazine-2,5-dione I；10700-97-3；(3S)-3r,6t-diisopropyl-4-methyl-morpholine-2,5-dione；(3S)-3r,6t-Diisopropyl-4-methyl-morpholin-2,5-dion；(3s,6r)-3,6-Di(propan-2-yl)-4-methyl-morpholine-2,5-dione；(3S,6R)-4-methyl-3,6-di(propan-2-yl)morpholine-2,5-dione
• CAS: 812788-12-8
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: ZVVKRSSQGWOPIS-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苄氧羰基-N-甲基-L-缬氨酸 在 palladium on activated charcoal 2-氯-1-甲基吡啶碘化物 、 氢气 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 (3S,6R)-3,6-二异丙基-4-甲基-2,5-吗啉二酮
  参考文献：
  名称：

  化学介体：Depsilairdin（一种含有新氨基酸的倍半萜二肽）的显着结构和宿主选择性。

  摘要：

  描述了Depsilairdin的化学结构测定，Depsilairdin是一种由植物病原真菌Leptosphaeriamaculans / Phoma lingam产生的高度选择性的植物毒素。为了阐明异常的化学结构，结合使用了NMR光谱数据和X射线晶体学。绝对构型是通过化学降解和（3S，6R）-3,6-二异丙基-2,5-吗啉二酮及其（3R，6S）和（3R，6R）立体异构体的合成而建立的。与真菌病原体相似，十足抑素仅在芥菜芥末叶片上引起强烈损害，而对相关物种未造成强烈损害。[结构：见文字]

  DOI：

  10.1021/ol0478786

文献信息

• Cook; Cox; Farmer, Journal of the Chemical Society, 1949, p. 1027
  作者：Cook、Cox、Farmer

  DOI：——

  日期：——
• Induced production of depsipeptides by co-culturing Fusarium tricinctum and Fusarium begoniae
  作者：Jian-ping Wang、Wenhan Lin、Victor Wray、Daowan Lai、Peter Proksch

  DOI：10.1016/j.tetlet.2013.03.005

  日期：2013.5

  A co-culture of Fusarium tricinctum and Fusarium begoniae induced the production of two new linear depsipeptides, subenniatins A and B (1-2), which were not detected when either of the two fungi was cultured alone. The structures of the new compounds were unambiguously determined by analysis of 1D, 2D NMR, and mass spectra, as well as by chemical transformation. Complex NMR spectra were observed for compounds 1 and 2, which were attributed to the presence of rotamers as revealed by 1D NOE and ROESY measurements. Structurally, compounds 1 and 2 are biogenetic building blocks of the cytotoxic enniatins B, B1, A1, and A, which are the major metabolites of F. tricinctum when this fungus is cultured alone. Compounds 1 and 2 were found to be inactive in cytotoxic and antibacterial assays. (C) 2013 Elsevier Ltd. All rights reserved.
• Chemical Mediators:  The Remarkable Structure and Host-Selectivity of Depsilairdin, a Sesquiterpenic Depsipeptide Containing a New Amino Acid
  作者：M. Soledade C. Pedras、Paulos B. Chumala、J. Wilson Quail

  DOI：10.1021/ol0478786

  日期：2004.11.1

  used a combination of NMR spectral data and X-ray crystallography. The absolute configuration was established using chemical degradation and synthesis of (3S,6R)-3,6-diisopropyl-2,5-morpholinedione and its (3R,6S) and (3R,6R) stereoisomers. Similar to the fungal pathogen, depsilairdin caused strong lesions only on brown mustard leaves but not on related species. [structure: see text]

  描述了Depsilairdin的化学结构测定，Depsilairdin是一种由植物病原真菌Leptosphaeriamaculans / Phoma lingam产生的高度选择性的植物毒素。为了阐明异常的化学结构，结合使用了NMR光谱数据和X射线晶体学。绝对构型是通过化学降解和（3S，6R）-3,6-二异丙基-2,5-吗啉二酮及其（3R，6S）和（3R，6R）立体异构体的合成而建立的。与真菌病原体相似，十足抑素仅在芥菜芥末叶片上引起强烈损害，而对相关物种未造成强烈损害。[结构：见文字]