ethyl (5R)-5-hydroxy-3-oxo-7-phenylheptanoate | 132895-22-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl (5R)-5-hydroxy-3-oxo-7-phenylheptanoate
• CAS: 132895-22-8
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: DQVARVHVYFZVNC-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (5R)-5-hydroxy-3-oxo-7-phenylheptanoate 生成 (4S,6R)-4-hydroxy-6-(2-phenylethyl)oxan-2-one
  参考文献：
  名称：

  .BETA.-Hydroxy-.DELTA.-lactones as chiral building blocks involving 1,3-dihydroxyl functions. 1. New strategies for stereoselective construction of 2-methyl-3,5-dihydroxy esters.

  摘要：

  合成了四种可能的2-甲基-3,5-二羟基酯衍生物异构体，这些异构体是自然产物合成中的有用构件，采用了以C3羟基为导向的β-羟基-δ-内酯和β,δ-二羟基酯的立体选择性甲基化方法进行合成。

  DOI：

  10.1248/cpb.38.2890
• 作为产物：
  描述：

  (3R)-5-phenylpent-1-en-3-ol 在 咪唑 、 iron(III) chloride 、 四丁基氟化铵 、 双氧水 、 sodium hydroxide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 35.0h， 生成 ethyl (5R)-5-hydroxy-3-oxo-7-phenylheptanoate
  参考文献：
  名称：

  Concise Stereoselective Total Synthesis of (4R, 6R)-Lactone Moiety Analog of Mevinoline and Compactin

  摘要：

  A simple and highly efficient synthetic route has been developed for analogue of HMGCo A reductase inhibitor (1). The strategy utilizes S-Corey-Bakshi-Shibata (CBS) reduction, FeCl3-catalyzed C-H insertion of ethyl diazoacetate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2012.754470

文献信息

• Stereoselective Synthesis of a Mevinic Acid Analogue
  作者：Gowravaram Sabitha、K. Sudhakar、Ch. Srinivas、J. Yadav

  DOI：10.1055/s-2007-965904

  日期：2007.3

  An efficient and versatile synthetic method for the stereoselective synthesis of a mevinic acid analogue is described. This approach uses a combination of a Cosford protocol with a catecholborane-mediated stereoselective reduction of acyclic P-hydroxy ketones to syn-1,3-diols, as key steps.

  描述了一种用于立体选择性合成甲维酸类似物的有效且通用的合成方法。该方法将 Cosford 方案与儿茶酚硼烷介导的无环 P-羟基酮立体选择性还原为 syn-1,3-二醇相结合，作为关键步骤。
• Organocatalytic Asymmetric Peroxidation of γ,δ-Unsaturated β-Keto Esters—A Novel Route to Chiral Cycloperoxides
  作者：Mary C. Hennessy、Hirenkumar Gandhi、Timothy P. O’Sullivan

  DOI：10.3390/molecules28114317

  日期：——

  A methodology for the asymmetric peroxidation of γ,δ-unsaturated β-keto esters is presented. Using a cinchona-derived organocatalyst, the target δ-peroxy-β-keto esters were obtained in high enantiomeric ratios of up to 95:5. Additionally, these δ-peroxy esters can be readily reduced to chiral δ-hydroxy-β-keto esters without impacting the β-keto ester functionality. Importantly, this chemistry opens

  介绍了 γ,δ-不饱和 β-酮酯的不对称过氧化方法。使用金鸡纳衍生的有机催化剂，以高达 95:5 的高对映体比例获得了目标 δ-过氧-β-酮酯。此外，这些 δ-过氧酯可以很容易地还原为手性 δ-羟基-β-酮酯，而不会影响 β-酮酯的功能。重要的是，这种化学通过一种新的 P2O5 介导的相应 δ-过氧-β-羟基酯的环化，为手性 1,2-二氧戊环（许多生物活性天然产物中的常见基序）开辟了一条简洁的途径。
• Concise Stereoselective Total Synthesis of (4<i>R</i>, 6<i>R</i>)-Lactone Moiety Analog of Mevinoline and Compactin
  作者：D. Chandra Rao、D. Kumar Reddy、B. Chinnababu、V. Shekhar、Y. Venkateswarlu

  DOI：10.1080/00397911.2012.754470

  日期：2013.11.17

  A simple and highly efficient synthetic route has been developed for analogue of HMGCo A reductase inhibitor (1). The strategy utilizes S-Corey-Bakshi-Shibata (CBS) reduction, FeCl3-catalyzed C-H insertion of ethyl diazoacetate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]
• .BETA.-Hydroxy-.DELTA.-lactones as chiral building blocks involving 1,3-dihydroxyl functions. 1. New strategies for stereoselective construction of 2-methyl-3,5-dihydroxy esters.
  作者：Mineo FUKUI、Seiichi OKAMOTO、Tadafumi SANO、Tadashi NAKATA、Takeshi OISHI

  DOI：10.1248/cpb.38.2890

  日期：——

  Four possible isomers of 2-methyl-3, 5-dihydroxy ester derivatives, useful building blocks for natural product synthesis, were synthesized stereoselectively using C3-hydroxyl-directed methylation of β-hydroxy-δ-lactone and β, δ-dihydroxy ester.

  合成了四种可能的2-甲基-3,5-二羟基酯衍生物异构体，这些异构体是自然产物合成中的有用构件，采用了以C3羟基为导向的β-羟基-δ-内酯和β,δ-二羟基酯的立体选择性甲基化方法进行合成。