(2E,4E,6E)-2-methylocta-2,4,6-trienal | 922185-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,4E,6E)-2-methylocta-2,4,6-trienal
• CAS: 922185-77-1
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: YOISLVMRMNQQLL-DTPQUVBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,4E,6E)-2-methylocta-2,4,6-trienal 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 36.0h， 生成 2-hydroxy-4-[(1E,3E,5E,7E)-3-methylnona-1,3,5,7-tetraen-1-yl]-2-pyranone
  参考文献：
  名称：

  Syntheses of Conjugated Pyrones for the Enzymatic Assay of Lovastatin Nonaketide Synthase, an Iterative Polyketide Synthase

  摘要：

  Lovastatin nonaketide synthase (LovB, LNKS) is an iterative type I polyketide synthase (PKS) from Aspergillus terreus that produces dihydromonacolin L (2), the biosynthetic precursor of lovastatin (1), from acetyl CoA, malonyl CoA, and S-adenosylmethionine (SAM) if the accessory protein LovC is present. In the absence of LovC, LNKS forms the conjugated pyrones 3 and 4 as truncated PKS products. Short syntheses of these pyrones provide material for the assay of LNKS activity by HPLC and radioisotope dilution analysis.

  DOI：

  10.1021/ol062763i
• 作为产物：
  描述：

  (E,E)-2,4-己二烯醛 在 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 65.0h， 生成 (2E,4E,6E)-2-methylocta-2,4,6-trienal
  参考文献：
  名称：

  Syntheses of Conjugated Pyrones for the Enzymatic Assay of Lovastatin Nonaketide Synthase, an Iterative Polyketide Synthase

  摘要：

  Lovastatin nonaketide synthase (LovB, LNKS) is an iterative type I polyketide synthase (PKS) from Aspergillus terreus that produces dihydromonacolin L (2), the biosynthetic precursor of lovastatin (1), from acetyl CoA, malonyl CoA, and S-adenosylmethionine (SAM) if the accessory protein LovC is present. In the absence of LovC, LNKS forms the conjugated pyrones 3 and 4 as truncated PKS products. Short syntheses of these pyrones provide material for the assay of LNKS activity by HPLC and radioisotope dilution analysis.

  DOI：

  10.1021/ol062763i

文献信息

• A Selective 3-Acylation of Tetramic Acids and the First Synthesis of Ravenic Acid
  作者：Andrea Schlenk、Randi Diestel、Florenz Sasse、Rainer Schobert

  DOI：10.1002/chem.200902544

  日期：2010.2.22

  3‐Acyltetramic acids, including delicate 3‐oligoenoyl derivatives, such as the Penicillium metabolite ravenic acid, were prepared in two high‐yielding steps. Reaction of tetramic acids with the ylide Ph3PCCO afforded exclusively the corresponding 3‐acylylidenetetramic acids. These were amenable to Wittig olefinations with aliphatic, aromatic, saturated and unsaturated aldehydes after deprotonation

  3-Acyltetramic acid，包括易碎的3-oligoenoyl衍生物，例如青霉代谢产物鼠尾草酸，是通过两个高产率步骤制备的。丁二酸与叶立德Ph 3 PCCO的反应仅提供了相应的3-酰亚乙基四丁酸。这些在用KO t Bu去质子化之后适合于用脂族，芳族，饱和和不饱和醛进行的维蒂希（Wittig）烯化。由于其简单性，对pH敏感基团的选择性和耐受性，该方法优于Jones和Yoshii建立的酰化方案。它也适用于3-酰基电子酸的合成。新的3-寡烯酰基四酸显示出结构依赖性的抗微生物和细胞毒性活性。
• Syntheses of Conjugated Pyrones for the Enzymatic Assay of Lovastatin Nonaketide Synthase, an Iterative Polyketide Synthase
  作者：Douglas A. Burr、Xuan B. Chen、John C. Vederas

  DOI：10.1021/ol062763i

  日期：2007.1.1

  Lovastatin nonaketide synthase (LovB, LNKS) is an iterative type I polyketide synthase (PKS) from Aspergillus terreus that produces dihydromonacolin L (2), the biosynthetic precursor of lovastatin (1), from acetyl CoA, malonyl CoA, and S-adenosylmethionine (SAM) if the accessory protein LovC is present. In the absence of LovC, LNKS forms the conjugated pyrones 3 and 4 as truncated PKS products. Short syntheses of these pyrones provide material for the assay of LNKS activity by HPLC and radioisotope dilution analysis.