(S)-benzyl 2-hydroxy-3-methylbut-3-enoate | 157087-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-benzyl 2-hydroxy-3-methylbut-3-enoate
• 英文别名: benzyl (S)-2-hydroxy-3-methylbut-3-enoate；3-Butenoic acid, 2-hydroxy-3-methyl-, phenylmethyl ester, (2S)-；benzyl (2S)-2-hydroxy-3-methylbut-3-enoate
• CAS: 157087-28-0
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: MXMSZHZINWJGPQ-NSHDSACASA-N

物化性质

• 沸点：
  323.7±27.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-hydroxy-3-methylbut-3-enoate 在 10% palladium on active carbon 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 bis(acetylacetonate)oxovanadium 、 氢气 、 三乙胺 作用下， 以 甲醇 、 癸烷 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoic acid
  参考文献：
  名称：

  Bryant, Helen J.; Dardonville, Christophe Y.; Hodgkinson, Timothy J., Journal of the Chemical Society. Perkin transactions I, 1998, # 7, p. 1249 - 1255

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基甲基3-甲基丁-2-烯酸酯 在 AD-mix-α 、 甲基磺酰胺 、 camphor-10-sulfonic acid 、 碳酸氢钠 、 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 115.0h， 生成 (S)-benzyl 2-hydroxy-3-methylbut-3-enoate
  参考文献：
  名称：

  Bryant, Helen J.; Dardonville, Christophe Y.; Hodgkinson, Timothy J., Journal of the Chemical Society. Perkin transactions I, 1998, # 7, p. 1249 - 1255

  摘要：

  DOI：

文献信息

• Design and synthesis of a DNA-crosslinking azinomycin analogue
  作者：Maxwell A. Casely-Hayford、Klaus Pors、Colin H. James、Laurence H. Patterson、John A. Hartley、Mark Searcey

  DOI：10.1039/b508908e

  日期：——

  The azinomycins are potent antitumour antibiotics that are able to crosslink DNA, but are relatively unstable and unlikely to progress as therapeutic candidates. A prototype analogue 4 with more clinical potential has been designed and synthesised and incorporates the epoxide function of the azinomycins and a nitrogen mustard. Two further analogues 5 and 6 that can alkylate DNA but cannot crosslink the duplex have also been synthesised. Compound 4 crosslinks DNA efficiently at nM concentrations. Compounds 4–6 were submitted to the NCI 60 cell line screen and have similar antitumour activity, although 4 is slightly less active than the non-crosslinking compounds. These observations will be important in the design of further azinomycin analogues with antitumour activity.

  氮霉素是一种能交联 DNA 的强效抗肿瘤抗生素，但相对不稳定，不太可能成为治疗候选药物。我们设计并合成了一种更有临床潜力的类似物原型 4，它结合了氮唑霉素的环氧化物功能和氮芥。此外，还合成了能烷基化 DNA 但不能交联双链的另两种类似物 5 和 6。化合物 4 在 nM 浓度下可有效交联 DNA。化合物 4-6 已提交给 NCI 60 细胞系筛选，具有相似的抗肿瘤活性，但化合物 4 的活性略低于非交联化合物。这些观察结果对于设计更多具有抗肿瘤活性的氮霉素类似物非常重要。
• Azinomycin bisepoxides containing rigid aromatic linkers: synthesis, cytotoxicity and DNA interstrand cross-linking activity
  作者：Matthew J. Finerty、John P. Bingham、John A. Hartley、Michael Shipman

  DOI：10.1016/j.tetlet.2009.03.123

  日期：2009.7

  bisepoxides containing rigid linkers is achieved through two different strategies. Double copper-mediated C–N bond formation under Buchwald-type conditions can be realised but yields are poor with fully intact epoxide substrates. The bisepoxides are made in improved yields through the simultaneous formation of two amide bonds. Bioassays reveal that 5, containing a 1,3-diaminobenzene linker, is a potent in

  一系列包含刚性接头的阿奇霉素双环氧化物的合成是通过两种不同的策略实现的。在布赫瓦尔德型条件下，可以实现双铜介导的C–N键的形成，但使用完整的环氧底物，收率很低。通过同时形成两个酰胺键可以提高收率。生物测定表明，含有1，3-二氨基苯连接基的5是一种有效的体外DNA链间交联剂，在NCI 60-人类癌细胞组中具有明显的细胞毒性（GI 50  = 0.15μM）。
• Exploration of the Molecular Origin of the Azinomycin Epoxide: Timing of the Biosynthesis Revealed
  作者：Vasudha Sharma、Gilbert T. Kelly、Coran M. H. Watanabe

  DOI：10.1021/ol8018852

  日期：2008.11.6

  Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.
• Synthesis of Functional “Top-Half” Partial Structures of Azinomycin A and B
  作者：Robert S. Coleman、Mark T. Tierney、Sarah B. Cortright、Daniel J. Carper

  DOI：10.1021/jo7014888

  日期：2007.9.1

  [GRAPHICS]The design and synthesis of a detailed series of functional "top-half" substructures of azinomycin A and B is described.
• Chemical synthesis and cytotoxicity of some azinomycin analogues devoid of the 1-azabicyclo[3.1.0]hexane subunit
  作者：Timothy J. Hodgkinson、Lloyd R. Kelland、Michael Shipman、Franck Suzenet

  DOI：10.1016/s0960-894x(99)00663-0

  日期：2000.2

  A series of compounds related to the left-hand domain of the azinomycins have been made and evaluated for cytotoxic activity against a small panel of human tumour cell lines. The epoxide ring is shown to be essential for biological activity. Cytotoxicity is also shown to be sensitive to changes in the substitution pattern on the aromatic ring and the amide group. (C) 2000 Elsevier Science Ltd. All rights reserved.