(3S,4R,5S)-3-butyl-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-2(3H)-furanone | 214210-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4R,5S)-3-butyl-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-2(3H)-furanone
• 英文别名: (3S,4R,5S)-3-butyl-4-(dimethyl(phenyl)silyl)-5-methyldihydrofuran-2(3H)-one；(3S,4R,5S)-3-butyl-4-[dimethyl(phenyl)silyl]-5-methyloxolan-2-one
• CAS: 214210-35-2
• 化学式: C₁₇H₂₆O₂Si
• 分子量: 290.478
• InChiKey: KPGAKVLDQFRUNF-IMJJTQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-3-butyl-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-2(3H)-furanone 在 过氧乙酸 、 sodium acetate 、 溶剂黄146 、 potassium bromide 作用下， 反应 2.0h， 以93%的产率得到blastmycinolactol
  参考文献：
  名称：

  有机合成中的碲：丁烯醇和丁醇化物的通用方法

  摘要：

  使用羟基-乙烯基碲化物以高对映体纯度制备了天然存在的丁醇化物（-）-blastmycinactactol，（+）-blastmycinone，（-）-NFX-2，（+）-anticincinone以及丁烯内酯Acaterin的四种立体异构体。作为起始原料。

  DOI：

  10.1016/j.tet.2012.07.088
• 作为产物：
  描述：

  methyl (E)-pent-3-enoate 在 AD-mix-α 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 241.0h， 生成 (3S,4R,5S)-3-butyl-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-2(3H)-furanone
  参考文献：
  名称：

  Brief syntheses of (+)-blastmycinone and related γ-lactones from an asymmetrically dihydroxylated carboxylic ester

  摘要：

  A method for synthesizing optically active trans,trans-configurated alpha,beta,gamma-substituted gamma-lactones is presented. Asymmetric hydroxylation of ester 8 with AD mix alpha (AD mix beta) and subsequent dehydration provided butenolide S-6 (R-6). Conjugate addition of Li-2(Me2PhSi)(2)Cu(CN) to S-6 followed by alkylation of the resulting enolate led to the stereopure silyllactones 9-11. They furnished the title compounds after oxidative removal of the Me2PhSi group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00687-5

文献信息

• Tellurium in organic synthesis: a general approach to buteno- and butanolides
  作者：Renan S. Ferrarini、Alcindo A. Dos Santos、João V. Comasseto

  DOI：10.1016/j.tet.2012.09.074

  日期：2012.12

  The naturally occurring butanolides (−)-blastmycinolactol, (+)-blastmycinone, (−)-NFX-2, (+)-antimycinone as well as the four stereoisomers of the butenolide Acaterin were prepared in high enantiomeric purity using hydroxy-vinyl tellurides as starting materials.

  使用羟基-乙烯基碲化物以高对映体纯度制备了天然存在的丁醇化物（-）-blastmycinactactol，（+）-blastmycinone，（-）-NFX-2，（+）-anticincinone以及丁烯内酯Acaterin的四种立体异构体。作为起始原料。
• Tellurium in organic synthesis: a new approach to trisubstituted γ-butyrolactones with trans–trans relative stereochemistry. Total enantioselective synthesis of (−)-Blastmycinolactol, (+)-Blastmycinone, (−)-NFX-2, and (+)-Antimycinone
  作者：Renan S. Ferrarini、Alcindo A. Dos Santos、João V. Comasseto

  DOI：10.1016/j.tetlet.2010.10.089

  日期：2010.12

  The total synthesis of (-)-Blastmycinolactol, (+)-Blastmycinone, (-)-NFX-2, and (+)-Antimycinone was accomplished in few steps in high yields and ee, starting from enantiomerically enriched (S)-Z-vinylic hydroxytellurides. (C) 2010 Published by Elsevier Ltd.
• Brief syntheses of (+)-blastmycinone and related γ-lactones from an asymmetrically dihydroxylated carboxylic ester
  作者：Thilo Berkenbusch、Reinhard Brückner

  DOI：10.1016/s0040-4020(98)00687-5

  日期：1998.9

  A method for synthesizing optically active trans,trans-configurated alpha,beta,gamma-substituted gamma-lactones is presented. Asymmetric hydroxylation of ester 8 with AD mix alpha (AD mix beta) and subsequent dehydration provided butenolide S-6 (R-6). Conjugate addition of Li-2(Me2PhSi)(2)Cu(CN) to S-6 followed by alkylation of the resulting enolate led to the stereopure silyllactones 9-11. They furnished the title compounds after oxidative removal of the Me2PhSi group. (C) 1998 Elsevier Science Ltd. All rights reserved.
• NHC–Cu(i) catalysed asymmetric conjugate silyl transfer to unsaturated lactones: application in kinetic resolution
  作者：Vittorio Pace、James P. Rae、Hassan Y. Harb、David J. Procter

  DOI：10.1039/c3cc42160k

  日期：——

  The scope of the asymmetric silyl transfer to unsaturated lactones utilising a C2-symmetric NHC–Cu(I) catalyst has been established and kinetic resolutions mediated by silyl transfer have been used to prepare enantiomerically enriched anti-4,5-disubstituted 5-membered lactones. The method has been exploited in an expedient synthesis of (+)-blastmycinone.

  利用 C2 对称 NHCâCu(I) 催化剂对不饱和内酯进行不对称硅基转移的范围已经确定，并利用硅基转移介导的动力学解析制备了对映体富集的反 4,5 二取代 5 元内酯。该方法已被用于 (+)-blastmycinone 的快速合成。