(R)-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carbaldehyde | 118100-81-5

• 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: (R)-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carbaldehyde
• 英文别名: (R)-6-(benzyloxy)-2,5,7,8-tetramethylchromane-2-carbaldehyde；(2R)-2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromene-2-carbaldehyde
• CAS: 118100-81-5
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: RIMUAYZWJHXSJG-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carbaldehyde 在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 48.0h， 生成 (S)-2-(12-hydroxydodecyl)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-ol
  参考文献：
  名称：

  生育酚脂肪醇及其类似物的合成得到改善：小胶质细胞活化调节剂

  摘要：

  强大的小胶质细胞活化调节剂生育酚脂肪醇（TFA）的合成是通过三甲基氢醌的C-烷基化实现的。使用维蒂希反应已经合成了几种类似物，特别是水溶性前药，并且已经评估了它们的抗氧化活性。

  DOI：

  10.1016/j.tet.2006.09.082
• 作为产物：
  描述：

  [(2S)-6-hydroxy-2-(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-2-yl]methyl acetate 在 sodium tetrahydroborate 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (R)-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carbaldehyde
  参考文献：
  名称：

  Synthesis of (S)-α-tocotrienol via an enzymatic desymmetrization of an achiral chroman derivative

  摘要：

  The stereoselective acylation of an achiral chromandimethanol derivative by vinyl acetate in the presence of Candida antarctica lipase in organic media gave the corresponding (S)-monoester in high enantiomeric purity (ee=98%). (S)-alpha-Tocotrienol was synthesized in 19% overall yield over six steps from this (S)-monoester. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01865-8

文献信息

• Screening of a virtual mirror-image library of natural products
  作者：Taro Noguchi、Shinya Oishi、Kaori Honda、Yasumitsu Kondoh、Tamio Saito、Hiroaki Ohno、Hiroyuki Osada、Nobutaka Fujii

  DOI：10.1039/c6cc03114e

  日期：——

  We established a facile access to an unexplored mirror-image library of chiral natural product derivatives using D-protein technology. In this process, two chemical syntheses of mirror-image substances including a target...

  我们使用D蛋白技术轻松访问未开发的手性天然产物衍生物的镜像库。在此过程中，包括目标物在内的镜像物质的两种化学合成...
• Synthesis of (S)-α-tocotrienol via an enzymatic desymmetrization of an achiral chroman derivative
  作者：Robert Chênevert、Gabriel Courchesne

  DOI：10.1016/s0040-4039(02)01865-8

  日期：2002.10

  The stereoselective acylation of an achiral chromandimethanol derivative by vinyl acetate in the presence of Candida antarctica lipase in organic media gave the corresponding (S)-monoester in high enantiomeric purity (ee=98%). (S)-alpha-Tocotrienol was synthesized in 19% overall yield over six steps from this (S)-monoester. (C) 2002 Elsevier Science Ltd. All rights reserved.
• CHAN, KA-KONG;SAUCY, GABRIEL G.
  作者：CHAN, KA-KONG、SAUCY, GABRIEL G.

  DOI：——

  日期：——
• Improved synthesis of tocopherol fatty alcohols and analogs: microglial activation modulators
  作者：Thierry Muller、Djalil Coowar、Mazen Hanbali、Paul Heuschling、Bang Luu

  DOI：10.1016/j.tet.2006.09.082

  日期：2006.12

  The synthesis of tocopherol fatty alcohols (TFAs), potent microglial activation modulators, was achieved via C-alkylation of trimethylhydroquinone. Several analogs, in particular water-soluble prodrugs, have been synthesized using a Wittig reaction and their antioxidant activities have been evaluated.

  强大的小胶质细胞活化调节剂生育酚脂肪醇（TFA）的合成是通过三甲基氢醌的C-烷基化实现的。使用维蒂希反应已经合成了几种类似物，特别是水溶性前药，并且已经评估了它们的抗氧化活性。
• Chemoenzymatic synthesis of both enantiomers of α-tocotrienol
  作者：Robert Chênevert、Gabriel Courchesne、Nicholas Pelchat

  DOI：10.1016/j.bmc.2006.03.035

  日期：2006.8

  The stereoselective acylation of the achiral chromanedimethanol derivative 1 by vinyl acetate in the presence of Candida antarctica lipase B gave the (S)-monoester 2 in high enantiomeric purity (ee >= 98%). Enzymatic hydrolysis of diesters of compound I failed to give (R)-monoester 2 in good yield and high ee. Thus, both enantiomers of alpha-tocotrienol were synthesized from the (S)-monoester 2. (c) 2006 Elsevier Ltd. All rights reserved.