(2E)-4-(Methoxymethoxy)-3-methyl-2-buten-1-OL | 109788-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E)-4-(Methoxymethoxy)-3-methyl-2-buten-1-OL
• 英文别名: (E)-4-(methoxymethoxy)-3-methylbut-2-en-1-ol
• CAS: 109788-40-1
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: PUTFYWYLILXXEU-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-4-(Methoxymethoxy)-3-methyl-2-buten-1-OL 在 六甲基磷酰三胺 、 N-氯代丁二酰亚胺 、 二甲基硫 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of the upper spirotetronic acid fragment of kijanolide

  摘要：

  DOI：

  10.1021/jo00227a040
• 作为产物：
  描述：

  梨醇酯 在 叔丁基过氧化氢 、 lithium hydroxide 、 selenium(IV) oxide 、 大茴香酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.0h， 生成 (2E)-4-(Methoxymethoxy)-3-methyl-2-buten-1-OL
  参考文献：
  名称：

  Exploration of conjugate addition routes to advanced tricyclic components of mangicol A

  摘要：

  Two synthetic approaches to the cytotoxic marine natural product known as mangicol A are described. The starting material common to both pathways is the cyclopentenonecarboxylate 11. The first tactic involves the 1,4-addition to 11 of the cuprate derivable from iodide 10, while the second proceeds via base-promoted conjugate addition of the regiospecifically generated enolate anion of 41. The first strategy proceeds by a series of efficient steps to tricyclic aldol 21 and subsequently to beta-diketone 7. The latter proved to be totally unresponsive to schemes aimed at introduction of a butenyl group. The second approach involves earlier introduction of this substituent as realized in stereo-controlled fashion via transition state 42. While further passage to 44 proved uneventful, this advanced intermediate and analogs thereof proved remarkably recalcitrant to cyclization in the precedented fashion. In no instance was generation of a suitable product realized. These studies serve to underscore the extent to which steric considerations can complicate matters and the extent to which they must be skirted. Finally, a direct enantioselective route to the side chain aldehyde 2 is detailed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.066

文献信息

• Enantioselective Total Syntheses of (−)-Caulamidine D and (−)-Isocaulamidine D and Their Absolute Configuration Reassignment
  作者：Haiyong Yu、Junhao Zhang、Dongxu Ma、Xiaotong Li、Tao Xu

  DOI：10.1021/jacs.3c08714

  日期：2023.10.18

  The first enantioselective total syntheses of (−)-caulamidine D (5) and (−)-isocaulamidine D (6) were accomplished. Their absolute configurations were unambiguously elucidated through X-ray crystallography. The isolated natural samples of both 5 and 6 are determined to be the TFA salts instead of the neutral forms. It took 16 steps (longest linear sequence) to divergently access both 5 and 6 following

  首次对映选择性全合成了 (-)-球脒 D ( 5 ) 和 (-)-异球脒 D ( 6 )。通过 X 射线晶体学明确阐明了它们的绝对构型。分离的天然样品5和6被确定为TFA盐而不是中性形式。遵循统一策略，需要 16 个步骤（最长的线性序列）才能分别访问第5 步和第 6 步。关键反应包括 (1) 开发和应用不对称 Meerwein-Eschenmoser-Claisen 重排来构建具有挑战性的 C10、C23 连续立体中心，以及 (2) 级联 6- exo -dig/6- exo -tet 胺/腈的应用环化反应。
• Exploration of conjugate addition routes to advanced tricyclic components of mangicol A
  作者：Stefan Pichlmair、Manuel de Lera Ruiz、Ivan Vilotijevic、Leo A. Paquette

  DOI：10.1016/j.tet.2006.03.066

  日期：2006.6

  Two synthetic approaches to the cytotoxic marine natural product known as mangicol A are described. The starting material common to both pathways is the cyclopentenonecarboxylate 11. The first tactic involves the 1,4-addition to 11 of the cuprate derivable from iodide 10, while the second proceeds via base-promoted conjugate addition of the regiospecifically generated enolate anion of 41. The first strategy proceeds by a series of efficient steps to tricyclic aldol 21 and subsequently to beta-diketone 7. The latter proved to be totally unresponsive to schemes aimed at introduction of a butenyl group. The second approach involves earlier introduction of this substituent as realized in stereo-controlled fashion via transition state 42. While further passage to 44 proved uneventful, this advanced intermediate and analogs thereof proved remarkably recalcitrant to cyclization in the precedented fashion. In no instance was generation of a suitable product realized. These studies serve to underscore the extent to which steric considerations can complicate matters and the extent to which they must be skirted. Finally, a direct enantioselective route to the side chain aldehyde 2 is detailed. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of the upper spirotetronic acid fragment of kijanolide
  作者：Kei Takeda、Shingo Yano、Masaaki Sato、Eiichi Yoshii

  DOI：10.1021/jo00227a040

  日期：1987.9