3-hydroxy-2-methyleneoct-7-enoic acid methyl ester | 239079-29-9

• 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: 3-hydroxy-2-methyleneoct-7-enoic acid methyl ester
• 英文别名: Methyl 3-hydroxy-2-methylene-7-octenoate；methyl 3-hydroxy-2-methylideneoct-7-enoate
• CAS: 239079-29-9
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: RQGCWAMIBNPZPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-hydroxy-2-methyleneoct-7-enoic acid methyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到methyl 6-hydroxy-cyclohex-1-enecarboxylate
  参考文献：
  名称：

  Intramolecular Morita–Baylis–Hillman adducts via sequential MBH and ring-closing-metathesis reactions

  摘要：

  Using a tandem Morita-Baylis-Hiliman (MBH) and ring-closing-metathesis (RCM) sequence, an alternative high yielding method for the construction of intramolecular Morita-Baylis-Hillman (IMBH) mono- and bicyclic functionalized cycloalkenols is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.066
• 作为产物：
  描述：

  5-己烯醛 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 以71%的产率得到3-hydroxy-2-methyleneoct-7-enoic acid methyl ester
  参考文献：
  名称：

  直接，高度收敛的路线稠合至大中环的α-亚甲基-γ-内酯

  摘要：

  描述了合成α-亚甲基内酯顺式或反式稠合至较大环的一般方法。方便的方法源自链长相同或不同的两个ω-不饱和醛。

  DOI：

  10.1016/s0040-4039(99)00781-9

文献信息

• Synthesis of <i>cis</i>-Fused Carbo-Bicycles by Domino Enyne Cross-Metathesis/Intramolecular Diels−Alder Reaction
  作者：Stefan Mix、Siegfried Blechert

  DOI：10.1021/ol050508c

  日期：2005.5.1

  A sequential combination of Ru-catalyzed enyne cross-metathesis (EYCM) and intramolecular Diels-Alder reaction (IMDA) is described. Different terminal alkynes and alpha,omega-dienes obtained by a Baylis-Hillman reaction were transformed into substituted cis-hexahydro-1H-indenes and cis-hexahydro-2H-naphthalin-1-ones.

  描述了Ru催化的烯炔跨复分解（EYCM）和分子内Diels-Alder反应（IMDA）的顺序组合。通过Baylis-Hillman反应获得的不同的末端炔烃和α，ω-二烯被转化为取代的顺式-六氢-1H-茚和顺式-六氢-2H-萘-1-酮。
• Tandem Development of Aqueous Indium Chemistry and Ring-Closing Metathesis as a General Route to Fused-Ring α-Methylene-γ-butyrolactones
  作者：José Méndez-Andino、Leo??A. Paquette

  DOI：10.1002/1615-4169(200206)344:3/4<303::aid-adsc303>3.0.co;2-j

  日期：2002.6

  reaction into a functionalized allylic bromide. Merger of the two building blocks is subsequently accomplished in aqueous solution with powdered indium metal serving as the initiator. Once the lactone ring is crafted, the end products are generated by application of ring-closing metathesis. The central issues surrounding this final step are the effects of the stereochemical disposition of the side chains

  报告了针对顺式或反式融合到较大环的α-亚甲基内酯的一般合成的程序。该协议源于两个链长相同或不同的 ω-不饱和醛。其中之一最初通过 Baylis-Hillman 反应转化为功能化的烯丙基溴化物。随后在水溶液中以粉状铟金属作为引发剂，实现两个结构单元的合并。内酯环制成后，通过应用闭环复分解生成最终产品。围绕这最后一步的核心问题是侧链的立体化学布置的影响、环应变的后果以及双键的位置对环化效率的影响。
• Intramolecular Morita–Baylis–Hillman adducts via sequential MBH and ring-closing-metathesis reactions
  作者：Marie E. Krafft、Eun-Ho Song、Ryan J. Davoile

  DOI：10.1016/j.tetlet.2005.07.066

  日期：2005.9

  Using a tandem Morita-Baylis-Hiliman (MBH) and ring-closing-metathesis (RCM) sequence, an alternative high yielding method for the construction of intramolecular Morita-Baylis-Hillman (IMBH) mono- and bicyclic functionalized cycloalkenols is reported. (c) 2005 Elsevier Ltd. All rights reserved.
• A direct, highly convergent route to α-methylene-γ-lactones fused to medium and large rings
  作者：Leo A. Paquette、José Méndez-Andino

  DOI：10.1016/s0040-4039(99)00781-9

  日期：1999.6

  A general procedure for the synthesis of α-methylene lactones cis- or trans-fused to larger rings is described. The convenient approach originates with two ω-unsaturated aldehydes of the same or different chain length.

  描述了合成α-亚甲基内酯顺式或反式稠合至较大环的一般方法。方便的方法源自链长相同或不同的两个ω-不饱和醛。