2-[(2S)-2-p-methoxybenzyloxy-4-pentenyl]-1,3-dithiane | 322428-39-7

• 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: 2-[(2S)-2-p-methoxybenzyloxy-4-pentenyl]-1,3-dithiane
• 英文别名: 2-[(2S)-2-[(4-methoxyphenyl)methoxy]pent-4-enyl]-1,3-dithiane
• CAS: 322428-39-7
• 化学式: C₁₇H₂₄O₂S₂
• 分子量: 324.508
• InChiKey: KMFMMOFLVLNUSI-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2S)-2-p-methoxybenzyloxy-4-pentenyl]-1,3-dithiane 在 三氟化硼乙醚 、 水 、 calcium carbonate 、 碘甲烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 11.5h， 生成 4-[(3R,5S)-3-hydroxy-5-(p-methoxybenzyloxy)-7-octenoyl]-2-((E)-2-phenylethenyl)oxazole
  参考文献：
  名称：

  Total synthesis of (−)-hennoxazole A

  摘要：

  The antiviral marine natural product (-)-hennoxazole A was efficiently synthesized by a convergent approach. The stereoselective synthesis of the functionalized tetrahydropyran fragment was accomplished by the Mukaiyama aldol reaction, chelation-controlled 1,3-syn reduction, Wacker oxidation, and acid catalyzed intramolecular ketalization. The nonconjugated triene fragment was synthesized by S(N)2 displacement of an allylic bromide with vinyllithium and the CrCl2-mediated iodoolefination followed by palladium-catalyzed cross coupling with MeMgBr. The final steps include the fragment coupling using DEPC and oxazole synthesis via an oxidation/cyclodehydration process. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00593-2
• 作为产物：
  描述：

  (S)-2-allyloxirane 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-[(2S)-2-p-methoxybenzyloxy-4-pentenyl]-1,3-dithiane
  参考文献：
  名称：

  Total synthesis of the proposed structure of iriomoteolide-1a

  摘要：

  Full details of the total synthesis of the proposed structure of iriomoteolide-1a (1) are described. The key steps include (i) a Sakurai reaction between allylsilane 11 and aldehyde 10 that bears both a tertiary chiral center and vinyl iodide moiety (ii) an anti-aldol reaction to construct the C18/C19 chiral centers (iii) a B-alkyl Suzuki-Miyaura coupling reaction to assemble the C7-C23 fragment, and (iv) a macrocyclic ring-closing metathesis to complete the construction of the target molecule. Two different approaches to access penultimate precursor 2 are delineated. The NMR spectra of the synthetic iriomoteolide-1a (1) were found not to match those reported for the natural product bringing into question its true structural identity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.066

文献信息

• Total Synthesis of the Antiviral Marine Natural Product (−)-Hennoxazole A
  作者：Fumiaki Yokokawa、Toshinobu Asano、Takayuki Shioiri

  DOI：10.1021/ol000305i

  日期：2000.12.1

  [structure:see text] The marine natural product hennoxazole A was synthesized by a convergent approach. The diastereoselective Mukaiyama aldol reaction with beta-alkoxy aldehyde was used to construct the tetrahydropyran segment, and the preparation of the nonconjugated triene moiety was accomplished via S(N)2 displacement of allylic bromide with vinyllithium and Takai's iodoolefination followed by

  [结构：见正文]通过收敛方法合成了海洋天然产物己诺唑A。非对映选择性的Mukaiyama醛醇与β-烷氧基醛的反应被用于构建四氢吡喃链段，并通过乙烯基乙烯基锂的烯丙基溴的S（N）2置换和Takai的碘代烯烃反应，然后钯催化的交叉偶联来完成非共轭三烯部分的制备。与MeMgBr。最终步骤涉及使用DEPC的酰胺偶联和经由氧化/环脱水过程的恶唑合成。
• Total synthesis of the proposed structure of iriomoteolide-1a
  作者：Jun Xie、Yuelong Ma、David A. Horne

  DOI：10.1016/j.tet.2011.07.066

  日期：2011.9

  Full details of the total synthesis of the proposed structure of iriomoteolide-1a (1) are described. The key steps include (i) a Sakurai reaction between allylsilane 11 and aldehyde 10 that bears both a tertiary chiral center and vinyl iodide moiety (ii) an anti-aldol reaction to construct the C18/C19 chiral centers (iii) a B-alkyl Suzuki-Miyaura coupling reaction to assemble the C7-C23 fragment, and (iv) a macrocyclic ring-closing metathesis to complete the construction of the target molecule. Two different approaches to access penultimate precursor 2 are delineated. The NMR spectra of the synthetic iriomoteolide-1a (1) were found not to match those reported for the natural product bringing into question its true structural identity. (C) 2011 Elsevier Ltd. All rights reserved.
• Total synthesis of (−)-hennoxazole A
  作者：Fumiaki Yokokawa、Toshinobu Asano、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)00593-2

  日期：2001.7

  The antiviral marine natural product (-)-hennoxazole A was efficiently synthesized by a convergent approach. The stereoselective synthesis of the functionalized tetrahydropyran fragment was accomplished by the Mukaiyama aldol reaction, chelation-controlled 1,3-syn reduction, Wacker oxidation, and acid catalyzed intramolecular ketalization. The nonconjugated triene fragment was synthesized by S(N)2 displacement of an allylic bromide with vinyllithium and the CrCl2-mediated iodoolefination followed by palladium-catalyzed cross coupling with MeMgBr. The final steps include the fragment coupling using DEPC and oxazole synthesis via an oxidation/cyclodehydration process. (C) 2001 Elsevier Science Ltd. All rights reserved.