(6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one | 397871-03-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one
• 英文别名: (6r)-6[(e,4r,6r)-4,6-Dihydroxy-10-phenyl-1-decenyl]-5,6-dihydro-2h-2-pyrone；(2R)-2-[(E,4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-2,3-dihydropyran-6-one
• CAS: 397871-03-3
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: OCGNKBVINPNQAB-ROZNDYPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one 在 对甲苯磺酸 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 5.0h， 以53.7%的产率得到(6R)-6-{3-[(4R,6R)-2,2-dimethyl-6-(4-phenylbutyl)-1,3-dioxan-4-yl]prop-1-1-enyl}-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Absolute Configuration of Two New 6-Alkylatedα-Pyrones (=2H-Pyran-2-ones) fromRavensara crassifolia

  摘要：

  The stem bark CH2Cl2 extract of Ravensara crassifolia showed antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum in a bioautographic TLC assay. Activity-guided fractionation afforded two new alpha -pyrones : (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one (1) and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one (2). Their structures and absolute configurations were established by NMR spectroscopy, chemical methods, and CD spectroscopy. The antifungal activity against C. cucumerinum was determined for both compounds.

  DOI：

  10.1002/1522-2675(20011114)84:11<3470::aid-hlca3470>3.0.co;2-k
• 作为产物：
  描述：

  6-苯基-1-己烯 在 咪唑 、 4-二甲氨基吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate 、 正丁基锂 、 18-冠醚-6 、 (R,R)-(salen)Co(III)(OAc) 、 三氟化硼乙醚 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 苯 为溶剂， 生成 (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  First stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one

  摘要：

  A stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one is reported. The strategy utilizes an iterative Jacobsen hydrolytic kinetic resolution, ring opening with a chiral propargylic synthon and a preferential (Z)-Wittig olefination reaction and lactonization as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.056

文献信息

• Stereoselective total synthesis of (+)-strictifolione and (6R)-6[(E,4R,6R)-4,6-dihydro-10-phenyl-1-decenyl)-5,6-dihydro-2H-2-pyrone
  作者：Biswanath Das、Boyapati Veeranjaneyulu、Penagaluri Balasubramanyam、Malampati Srilatha

  DOI：10.1016/j.tetasy.2010.11.003

  日期：2010.12

  The stereoselective total synthesis of two naturally occurring α-pyrone derivatives, (+)-strictifolione and (6R)-6[(E,4R,6R)-4,6-dihydroxy-10-phenyl-1-decanyl]-5,6-dihydro-2H-2-pyrone has been accomplished involving the Sharpless kinetic resolution and olefin cross-metathesis as the key reactions.

  两种天然存在的α-吡喃酮衍生物，（+）-strictifolione和（6 R）-6 [（E，4 R，6 R）-4,6-二羟基-10-苯基-1-癸基]的立体选择性全合成已经完成了-5,6-二氢-2 H -2-吡喃酮的合成，其中包括Sharpless动力学拆分和烯烃交叉复分解反应。
• Stereoselective total synthesis of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one by Prins reaction and olefin cross-metathesis
  作者：Gowravaram Sabitha、Narjis Fatima、Peddabuddi Gopal、C. Nagendra Reddy、Jhillu S. Yadav

  DOI：10.1016/j.tetasy.2008.12.004

  日期：2009.2

  Prins and olefin cross-metathesis reactions were used as the key steps for the stereoselective total synthesis of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one. Removal of MOM protecting groups under neutral conditions using CeCl3·7H2O is an attractive addition to the present strategy.

  Prins和烯烃的交叉复分解反应被用作（+）-strictifolione和（6 R）-6-[（4 R，6 R）-4,6-二羟基-10-苯基癸酸酯的立体选择性全合成的关键步骤-1-烯基] -5，6-二氢-2 H-吡喃-2-一。使用CeCl 3 ·7H 2 O在中性条件下去除MOM保护基是本策略的一项有吸引力的补充。
• An Efficient, Modular Approach for the Synthesis of (+)-Strictifolione and a Related Natural Product
  作者：Susanthi Jayasinghe、Phanindra K. M. Venukadasula、Paul R. Hanson

  DOI：10.1021/ol403110p

  日期：2014.1.3

  An efficient, library amenable, “pot economical” total synthesis of (+)-strictifolione and the related natural product, (6R)-6[(E,4R,6R)-4,6-dihydroxy-10-phenyl-1-decenyl]-5,6-dihydro-2H-2-pyrone, are reported. This modular approach takes advantage of two consecutive phosphate tether-mediated, one-pot, sequential protocols, followed by a final cross metathesis to deliver both antifungal natural products

  (+)-strictifolione 和相关天然产物 (6 R )-6[( E ,4 R ,6 R )-4,6-dihydroxy-10-phenyl的高效、适合图书馆的“盆栽经济”全合成-1-癸烯基] -5,6-二氢-2- ħ -2-吡喃酮报告。这种模块化方法利用两个连续的磷酸盐系链介导的单锅顺序方案，然后进行最终的交叉复分解，在三锅过程中从各自的对映体 ( R , R )-和 (小号，小号)-三烯的纯化最少。该路线的一个显着特征是由于磷酸三酯固有的正交保护和离去基团特性，不需要额外的保护基团。
• A Stereoselective Aldol Approach for the Total Syntheses of Two 6-Alkylated 2<i>H</i>-Pyran-2-ones
  作者：Singanaboina Rajaram、Dasari Ramesh、Udugu Ramulu、Peddikotla Prabhakar、Yenamandra Venkateswarlu

  DOI：10.1002/hlca.201300139

  日期：2014.1

  A simple and highly efficient stereoselective total synthesis of the 6‐alkylated pyranones (6R)‐6‐[(1E,4R,6R)‐4,6‐dihydroxy‐10‐phenyldec‐1‐en‐1‐yl]‐5,6‐dihydro‐2H‐pyran‐2‐one (1) and (6S)‐5,6‐dihydro‐6‐[(2R)‐2‐hydroxy‐6‐phenylhexyl]‐2H‐pyran‐2‐one (2) was developed using Crimmins' aldol reaction, SmI2 reduction, Grubbs‐II‐catalyzed olefin cross‐metathesis, and Still's modified HornerWadsworthEmmons

  6烷基化吡喃酮（6 R）-6 [[（1 E，4 R，6 R）-4,6-二羟基-10-苯基癸-1-烯-1-基]的简单高效立体选择性全合成] ‐5,6‐dihydro‐2 H ‐pyran‐2‐one（1）和（6 S）‐5,6‐dihydro‐6 ‐ [[（2 R）‐2‐hydroxy‐6‐phenylhexyl] ‐2 H吡喃-2-酮（2）使用开发克里敏斯'醛醇缩合反应，SMI 2还原，格鲁布斯- II催化的烯烃交叉复分解，和静止的改性霍纳沃兹沃思埃蒙斯反应。
• Concise Total Syntheses of (+)-Strictifolione and (6<i>R</i>)-6-[(4<i>R</i>,6<i>R</i>)-4,6-Dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2<i>H</i>-pyran-2-one
  作者：Shibing Tang、Xingang Xie、Xiaolei Wang、Liuer He、Ke Xu、Xuegong She

  DOI：10.1021/jo101875w

  日期：2010.12.3

  Concise and efficient asymmetric total syntheses of (+)-strictifolione 1 and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one 2 have been achieved based on the strategic application of one-pot double allylboration and ring-closing metathesis reactions. The total syntheses proceeded in only five and seven steps, respectively, from readily available 3-butenal and represent the shortest syntheses of 1 and 2 reported to date.