(S)-1-((4-methoxybenzyl)oxy)-4-methylpent-4-en-2-ol | 1315319-05-1

• 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)-1-((4-methoxybenzyl)oxy)-4-methylpent-4-en-2-ol
• 英文别名: (2S)-1-[(4-methoxyphenyl)methoxy]-4-methylpent-4-en-2-ol
• CAS: 1315319-05-1
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: FAKDGDAFAOYFCF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (S)-1-((4-methoxybenzyl)oxy)-4-methylpent-4-en-2-ol 在 Grubbs catalyst first generation 、 水 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 nujol 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.75h， 生成 (2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-methanol
  参考文献：
  名称：

  Stereoselective Synthesis of the C13-C28 Subunit of (-)-Laulimalide Utilizing an α-Chlorosulfide Intermediate

  摘要：

  A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An -chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively.

  DOI：

  10.1055/s-0033-1339493
• 作为产物：
  描述：

  4-甲氧基溴苄 在 titanium(IV) isopropylate 、 四氧化锇 、 S-1,1'-联-2-萘酚 、 四丁基碘化铵 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 nujol 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 73.25h， 生成 (S)-1-((4-methoxybenzyl)oxy)-4-methylpent-4-en-2-ol
  参考文献：
  名称：

  Stereoselective Synthesis of the C13-C28 Subunit of (-)-Laulimalide Utilizing an α-Chlorosulfide Intermediate

  摘要：

  A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An -chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively.

  DOI：

  10.1055/s-0033-1339493

文献信息

• Studies toward the Synthesis of an Oxazole-Based Analog of (−)-Zampanolide
  作者：Christian P. Bold、Cindy Klaus、Bernhard Pfeiffer、Jasmine Schürmann、Rafael Lombardi、Daniel Lucena-Agell、J. Fernando Díaz、Karl-Heinz Altmann

  DOI：10.1021/acs.orglett.1c00378

  日期：2021.3.19

  Studies are described toward the synthesis of an oxazole-based analog of (−)-zampanolide (2). Construction of (−)-dactylolide analog 22 was achieved via alcohol 5 and acid 4 through esterification and Horner–Wadsworth–Emmons (HWE)-based macrocyclization; however, attempts to attach (Z,E)-sorbamide to 22 proved unsuccessful. The C(8)–C(9) double bond of the macrocycle was prone to migration into conjugation

  已经描述了关于合成基于恶唑的（-）-扎曼醇化物（2）的类似物的研究。通过酯化作用和基于霍纳-沃兹沃斯-埃蒙斯（HWE）的大环化反应，通过醇5和酸4来构建（-）-缩水甘油类似物22。但是，尝试将（Z，E）-山梨酰胺连接到22上的尝试未成功。大环的C（8）–C（9）双键易于迁移至与恶唑环共轭，这通常可能会限制具有芳香族部分的扎曼醇化物类似物作为四氢吡喃替代品的用途。
• Enantioselective Total Synthesis of (−)-Zampanolide, a Potent Microtubule-Stabilizing Agent
  作者：Arun K. Ghosh、Xu Cheng

  DOI：10.1021/ol201626h

  日期：2011.8.5

  An enantioselective total synthesis of zampanolide has been accomplished using a novel DDQ/Brønsted acid promoted cyclization as the key reaction. The synthesis features cross-metathesis to construct the trisubstituted olefin and a ring-closing metathesis to form the macrolactone. The final N-acyl aminal formation was stereoselectively accomplished by an organocatalytic reaction.

  使用新型 DDQ/Brønsted 酸促进环化作为关键反应，完成了对映选择性全合成赞帕内酯。该合成具有交叉复分解以构建三取代烯烃和闭环复分解以形成大环内酯的特征。最终的N-酰基氨基形成是通过有机催化反应立体选择性地完成的。
• A Method for the Stereoselective Construction of the Hemiaminal Center in Zampanolides
  作者：Tobias M. Brütsch、Simone Berardozzi、Marlene L. Rothe、Mariano Redondo Horcajo、José Fernando Díaz、Karl-Heinz Altmann

  DOI：10.1021/acs.orglett.0c02974

  日期：2020.11.6

  involves the reaction of (Z,E)-sorbamide (3) with BINAL-H and subsequent amide transfer from a putative aluminum carboximidoate complex to the aldehyde moiety of a dactylolide precursor, such as 2 or 5. The method has enabled the efficient synthesis of 13-desmethylene-(−)-zampanolide (4), which was found to be an equipotent cell growth inhibitor as the natural product (−)-zampanolide (1).

  我们已经开发出一种新方法，用于立体选择性地建立Zampanolide型结构中的N-酰基半胱氨酸部分，该方法涉及（Z，E）-山梨酰胺（3）与BINAL-H的反应，以及随后从推定的羧酰亚胺铝中转移酰胺与一个Dactylolide前体的醛部分的复合物，如2或5。该方法使得能够有效合成13-去亚甲基-（-）-扎曼醇化物（4），发现它是天然产物（-）-扎曼醇化物（1）的一种等价细胞生长抑制剂。
• Total Synthesis of Potent Antitumor Macrolide (-)-Zampanolide: An Oxidative Intramolecular Cyclization-Based Strategy
  作者：Arun K. Ghosh、Xu Cheng、Ruoli Bai、Ernest Hamel

  DOI：10.1002/ejoc.201200286

  日期：2012.8

  enantioselective total synthesis of (-)-zampanolide, a macrolide marine natural product with high anti-cancer activity is described. For synthesis of the 4-methylene tetrahydropyran unit of (-)-zampanolide, initially, we relied upon an oxidative C-H activation of an alkenyl ether and intramolecular cyclization to provide the substituted tetrahydropyran ring. However, this strategy was unsuccessful

  详细描述了 (-)-zampanolide 的对映选择性全合成，这是一种具有高抗癌活性的大环内酯海洋天然产物。为了合成 (-)-zampanolide 的 4-亚甲基四氢吡喃单元，最初，我们依靠烯基醚的氧化 CH 活化和分子内环化来提供取代的四氢吡喃环。然而，这个策略并没有成功。随后，我们发现肉桂基醚对于成功的氧化分子内环化反应至关重要。该合成还具有交叉复分解反应以构建三取代烯烃，闭环复分解以形成高度官能化的大环内酯和手性磷酸促进 N-酰基氨基形成以立体选择性地提供 (-)-zampanolide 且收率良好.