(2E,4E,6E)-8-(Diethoxy-phosphoryl)-4,6-dimethyl-octa-2,4,6-trienoic acid methyl ester | 403706-87-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4E,6E)-8-(Diethoxy-phosphoryl)-4,6-dimethyl-octa-2,4,6-trienoic acid methyl ester
• 英文别名: methyl (2E,4E,6E)-8-diethoxyphosphoryl-4,6-dimethylocta-2,4,6-trienoate
• CAS: 403706-87-6
• 化学式: C₁₅H₂₅O₅P
• 分子量: 316.334
• InChiKey: FIKXVEUSHXQNGE-FANUIOHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R,7S,E)-5,7-bis(tert-butyldimethylsilyloxy)-2-methyloct-2-enal 、 (2E,4E,6E)-8-(Diethoxy-phosphoryl)-4,6-dimethyl-octa-2,4,6-trienoic acid methyl ester 在 lithium diisopropyl amide 作用下， 以 异丙醚 为溶剂， 以96%的产率得到2,4,6,8,10-Hexadecapentaenoic acid,13,15-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,6,10-trimethyl-, methylester, (2E,6E,8E,10E,13R,15S)-
  参考文献：
  名称：

  通过全合成确定Mycolactone C的结构。

  摘要：

  [结构：见正文]通过全合成，已确定Mycolactone C为C12'-脱氧Mycolactones A和B的Z-Delta4'5'-和E-Delta4'5'-几何异构体的大约1：1混合物。

  DOI：

  10.1021/ol0479996
• 作为产物：
  描述：

  (E)-4-((tert-butyldimethylsilyl)oxy)-2-methylbut-2-enal 在 pyridine-SO3 complex 、 四丁基氟化铵 、 三溴化磷 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 生成 (2E,4E,6E)-8-(Diethoxy-phosphoryl)-4,6-dimethyl-octa-2,4,6-trienoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of the Mycolactones

  摘要：

  [GRAPHICS]The first total synthesis of the mycolactones is reported. This work unambiguously confirms our earlier relative and absolute stereochemical assignment of the mycolactones.

  DOI：

  10.1021/ol0172828

文献信息

• Synthesis and Structure of Two New Mycolactones Isolated from <i>M. ulcerans</i> subsp. <i>shinshuense</i>
  作者：Sudhir M. Hande、Yuko Kazumi、W. George Lai、Katrina L. Jackson、Shinji Maeda、Yoshito Kishi

  DOI：10.1021/ol302072b

  日期：2012.9.7

  Two new mycolactones, mycolactones S1 and S2, were isolated from culture agar of Mycobacterium ulcerans subsp. shinshuense. Their structures were established in a three-step procedure: (1) probable structures were speculated from MS analysis; (2) candidates were synthesized; (3) HPLC profiles were established for identification of the natural products. Newly isolated mycolactones correspond to the "oxidized forms" of mycolactone NB, the causative toxin of Buruli ulcer, isolated from Mycobacterium ulcerans.
• Total Synthesis of the Mycolactones
  作者：Fengbin Song、Steve Fidanze、Andrew B. Benowitz、Yoshito Kishi

  DOI：10.1021/ol0172828

  日期：2002.2.1

  [GRAPHICS]The first total synthesis of the mycolactones is reported. This work unambiguously confirms our earlier relative and absolute stereochemical assignment of the mycolactones.
• Structure Determination of Mycolactone C via Total Synthesis
  作者：Ted C. Judd、Alexander Bischoff、Yoshito Kishi、Sarojini Adusumilli、Pamela L. C. Small

  DOI：10.1021/ol0479996

  日期：2004.12.1

  [structure: see text] By total synthesis, mycolactone C has been established as an approximately 1:1 mixture of Z-Delta4'5'- and E-Delta4'5'-geometric isomers of C12'-deoxymycolactones A and B.

  [结构：见正文]通过全合成，已确定Mycolactone C为C12'-脱氧Mycolactones A和B的Z-Delta4'5'-和E-Delta4'5'-几何异构体的大约1：1混合物。