(2R,4aS,8aS)-4a-hydroxy-2-methyl-3,4,4a,8a-tetrahydrobenzo-1(2H)-pyran-7 (8)-one | 1195113-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,4aS,8aS)-4a-hydroxy-2-methyl-3,4,4a,8a-tetrahydrobenzo-1(2H)-pyran-7 (8)-one
• 英文别名: (2R,4aS,8aS)-4a-hydroxy-2-methyl-3,4,4a,8a-tetrahydrobenzo-1(2H)-pyran-7(8H)-one；(2R,4aS,8aS)-4a-hydroxy-2-methyl-3,4,8,8a-tetrahydro-2H-chromen-7-one
• CAS: 1195113-91-7
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: SGNNVOMAMYNNEJ-JEZHCXPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (2R,4aS,8aS)-4a-hydroxy-2-methyl-3,4,4a,8a-tetrahydrobenzo-1(2H)-pyran-7 (8)-one 在 咪唑 、 4-二甲氨基吡啶 、 2-叠氮丙二酸二甲酯 、 cerium(III) chloride heptahydrate 、 Rh₂(OAc)4 、 sodium acetate 、 氟化氢吡啶 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 (+)-cephalosporolide B
  参考文献：
  名称：

  Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G

  摘要：

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.

  DOI：

  10.1021/ol402913m
• 作为产物：
  描述：

  (R)-4-(3-hydroxybutyl)-4-hydroxy-2,5-cyclohexadien-1-one 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以79%的产率得到(2R,4aS,8aS)-4a-hydroxy-2-methyl-3,4,4a,8a-tetrahydrobenzo-1(2H)-pyran-7 (8)-one
  参考文献：
  名称：

  十元内酯头孢菌素G及其C-3差向异构体的简明对映选择性合成

  摘要：

  一，二，三个选择性氧化是天然的十元内酯头孢菌素G及其C-3差向异构体的原子经济首次全合成的关键步骤（参见方案）。从天然酚（R）-杜鹃醇开始，仅需七个或八个步骤即可合成它们，其中包含最终靶标中存在的所有碳原子。

  DOI：

  10.1002/chem.200901735

文献信息

• Concise Enantioselective Synthesis of the Ten-Membered Lactone Cephalosporolide G and Its C-3 Epimer
  作者：Silvia Barradas、Antonio Urbano、M. Carmen Carreño

  DOI：10.1002/chem.200901735

  日期：2009.9.21

  One, two, three selective oxidations are the key steps in the atom‐economic first total synthesis of the natural ten‐membered lactone cephalosporolide G and its C‐3 epimer (see scheme). They have been synthesised in only seven or eight steps starting from the natural phenol (R)‐rhododendrol, which contains all the carbon atoms present in the final targets.

  一，二，三个选择性氧化是天然的十元内酯头孢菌素G及其C-3差向异构体的原子经济首次全合成的关键步骤（参见方案）。从天然酚（R）-杜鹃醇开始，仅需七个或八个步骤即可合成它们，其中包含最终靶标中存在的所有碳原子。
• Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G
  作者：Liyan Song、Yuan Liu、Rongbiao Tong

  DOI：10.1021/ol402913m

  日期：2013.11.15

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.