methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate | 954148-38-0

• 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: methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate
• 英文别名: methyl (1R,6S)-6-(phenylmethoxymethyl)cyclohex-3-ene-1-carboxylate
• CAS: 954148-38-0
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: NIKKLBZYQQAEKQ-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate 在 manganese(IV) oxide 、 selenium(IV) oxide 、 水 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 130.0h， 生成 (6S,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-ene-1,7-dione
  参考文献：
  名称：

  直接亚胺酰化：'Upenamide提议的结构的合成

  摘要：

  报道了两种提议的大环海洋天然产物'upenamide结构的合成。关键步骤是利用受保护的β-羟基酸直接亚胺酰化（DIA）来构建关键的三环ABC环系统。在最后一步使用Stille交叉偶联反应完成了大环化反应。

  DOI：

  10.1021/ol3030764
• 作为产物：
  描述：

  ((1R,6S)-6-(hydroxymethyl)cyclohex-3-en-1-yl)methyl acetate 在 lithium hydroxide 、 jones' reagent 、 magnesium oxide 、 乙酰氯 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 21.0h， 生成 methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate
  参考文献：
  名称：

  The First Synthesis of the ABC-Ring System of ‘Upenamide

  摘要：

  The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid 'upenamide (1) has been developed. All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective SeO2-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization-bicyclization procedure. Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (S)-malic acid derived building block.

  DOI：

  10.1021/ol701772d

文献信息

• Direct Imine Acylation: Synthesis of the Proposed Structures of ‘Upenamide
  作者：William P. Unsworth、Katherine A. Gallagher、Mickaël Jean、Jan Peter Schmidt、Louis J. Diorazio、Richard J. K. Taylor

  DOI：10.1021/ol3030764

  日期：2013.1.18

  The synthesis of the two proposed structures of macrocyclic marine natural product ‘upenamide is reported. The key step utilizes direct imine acylation (DIA) with a protected β-hydroxy acid to construct the key tricyclic ABC ring system. The macrocyclization was completed in the final step using a Stille cross-coupling reaction.

  报道了两种提议的大环海洋天然产物'upenamide结构的合成。关键步骤是利用受保护的β-羟基酸直接亚胺酰化（DIA）来构建关键的三环ABC环系统。在最后一步使用Stille交叉偶联反应完成了大环化反应。
• The First Synthesis of the ABC-Ring System of ‘Upenamide
  作者：Jan Peter Schmidt、Sandra Beltrán-Rodil、Rhona J. Cox、Graeme D. McAllister、Mark Reid、Richard J. K. Taylor

  DOI：10.1021/ol701772d

  日期：2007.9.1

  The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid 'upenamide (1) has been developed. All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective SeO2-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization-bicyclization procedure. Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (S)-malic acid derived building block.