(3R,4R,5S)-3-n-hexyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one | 92017-12-4

• 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: (3R,4R,5S)-3-n-hexyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one
• 英文别名: (4S,5R)-3-hexyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone；(3R,4R,5S)-3-hexyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one；(3S,4R,5R)-3-hexyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one；(2R,3R,4S)-2-hexyl-3-hydroxy-4-methylbutyrolactone；(2R,3R,4S)-2-Hexyl-3-hydroxy-4-pentanolide；(-)-Antimycinolactol；(3R,4R,5S)-3-hexyl-4-hydroxy-5-methyloxolan-2-one
• CAS: 92017-12-4；137171-30-3；137624-86-3；137624-87-4；137171-29-0
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: WJMRPSHNKKDPJZ-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (3R,4R,5S)-3-n-hexyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one 、 异戊酰氯 在 吡啶 作用下， 以96%的产率得到L-阿拉伯酸,2,5-二脱氧-2-己基-,g-内酯,3-(3-甲基丁酸酯)
  参考文献：
  名称：

  使用铬卡宾络合物的新内酯合成

  摘要：

  使用Fischer铬卡宾络合物开发了一种新的内酯合成方法。内酯由在系链中带有羟基或甲硅烷氧基的炔烃与铬卡宾络合物的卡宾碳和一氧化碳一起形成。使用该程序，在短时间内由（S）-乳酸乙酯合成了（+）-blastmycinone和（+）-antimycinone 。

  DOI：

  10.1016/0040-4039(96)01338-x
• 作为产物：
  描述：

  methyl (E)-pent-3-enoate 在 过氧乙酸 、 AD-mix-α 、 sodium acetate 、 甲基磺酰氯 、 三乙胺 、 potassium bromide 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 叔丁醇 为溶剂， 反应 262.0h， 生成 (3R,4R,5S)-3-n-hexyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one
  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。
• Asymmetric Synthesis of α-Alkylidene-β-hydroxy-γ-butyrolactones via Enantioselective Tandem Michael–Aldol Reaction
  作者：Sung Il Lee、Jin Hee Jang、Geum-Sook Hwang、Do Hyun Ryu

  DOI：10.1021/jo302369q

  日期：2013.1.18

  A simple and efficient method for the asymmetric synthesis of α-alkylidene-β-hydroxy-γ-butyrolactones and related natural products was developed on the basis of the catalytic asymmetric tandem Michael–aldol reaction and simple transformations. The synthetic utility of this method was illustrated by the facile synthesis of trisubstituted γ-butyrolactone natural products.

  在催化不对称串联Michael-aldol反应和简单转化的基础上，开发了一种简单高效的不对称合成α-亚烷基-β-羟基-γ-丁内酯和相关天然产物的方法。三取代γ-丁内酯天然产物的简便合成说明了该方法的合成效用。
• Reaction of chiral titanium Z-enolates with chiral α-silyloxy aldehydes. Syntheses of NFX-2 and Antimycinone
  作者：Cristina Esteve、Mònica Ferreró、Pedro Romea、Fèlix Urpí、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(99)00987-9

  日期：1999.7

  Titanium-mediated aldol reactions of 1 and (S)-2-tert-butyldiphenylsilyloxy aldehydes (matched pair) afford syn Felkin diastereomers in excellent yield and absolute stereochemical control. Having established that chain length does not affect the yield of the titanium aldol reactions we have been able to achieve short, high yielding and enantioselective syntheses of NFX-2 and Antimycinone.

  钛介导的1和（S）-2-叔丁基二苯基甲硅烷氧基醛（匹配对）的醇醛缩合反应可提供出色的收率和绝对的立体化学控制的合成Felkin非对映异构体。确定链长不会影响钛醇醛缩合反应的收率，我们已经能够实现NFX-2和抗霉素的短，高收率和对映选择性合成。
• Highly stereoselective titanium-mediated aldol reactions from chiral α-silyloxy ketones. A reliable tool for the synthesis of natural products
  作者：Judit Esteve、Carme Jiménez、Joaquim Nebot、Javier Velasco、Pedro Romea、Fèlix Urpí

  DOI：10.1016/j.tet.2011.06.019

  日期：2011.8

  Chiral α-silyloxy ketones participate in highly stereoselective TiCl4-mediated aldol reactions that afford diastereomerically pure syn–syn adducts in high yield irrespective of the R1 and R2 substituents flanking the carbonyl or the silicon protecting group. Further manipulation of the resulting aldol adducts provide in a straightforward manner highly functionalized fragments that facilitate the synthesis

  手性α-甲硅烷氧基酮参与高度立体选择性的TiCl 4介导的醛醇缩合反应，无论羰基或硅保护基旁的R 1和R 2取代基如何，都能以高收率获得非对映体纯的syn - syn加合物。所得醛醇加合物的进一步处理以直接的方式提供了高度官能化的片段，其促进了天然产物的合成。
• Enantiospecific Synthesis of Trisubstituted Butyrolactone Natural Products and Their Analogs
  作者：Mukund P. Sibi、Jianliang Lu、Chelsy L. Talbacka

  DOI：10.1021/jo961171i

  日期：1996.1.1

  A general methodology for the synthesis of highly substituted butyrolactones in enantiomerically pure form has been developed. The application of this process in a highly efficient synthesis of lactone natural products blastmycinone (1), NFX-2 (2), antimycinone (3), and NFX-4 (4) and two lipid metabolites (5, 6) are described. Additionally, the total synthesis of 5-epi-blastmycinone (22), 5-epi-NFX-2

  已经开发出合成对映体纯形式的高度取代的丁内酯的通用方法。描述了该方法在高效合成内酯天然产物blastmycinone（1），NFX-2（2），antimycinone（3）和NFX-4（4）以及两种脂质代谢物（5，6）中的应用。另外，还描述了5-表胚芽孢霉素（22），5-表-NFX-2（21b），5-表-NFX-4（21c）和脂质代谢产物类似物（19、20）的总合成。目标分子的总产率是迄今为止文献中报道的最高。