2,2-Bis(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-6-ol | 105857-77-0

• 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: 2,2-Bis(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-6-ol
• CAS: 105857-77-0
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: KGMZKCCNVQUQAB-UHFFFAOYSA-N

物化性质

• 沸点：
  459.7±45.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-Bis(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-6-ol 在 Candida antarctica lipase B 、 sodium tetrahydroborate 、 3 A molecular sieve 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 2H-1-苯并吡喃-2-甲醇,3,4-二氢-6-羟基-2,5,7,8-四甲基-,(2R)-
  参考文献：
  名称：

  Chemoenzymatic synthesis of both enantiomers of α-tocotrienol

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.03.035
• 作为产物：
  描述：

  6-(tert-butyldimethylsilyloxy)-5,7,8-trimethylchroman-2-one 在 盐酸 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 生成 2,2-Bis(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-6-ol
  参考文献：
  名称：

  Enantioselective functionalization of prochiral diols via chiral spiroketals: preparation of optically pure 2-substituted 1,3-propanediol derivatives and asymmetric synthesis of chroman ring and side chain of .alpha.-tocopherol

  摘要：

  DOI：

  10.1021/ja00236a034

文献信息

• 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.
• Enantioselective functionalization of prochiral diols via chiral spiroketals: preparation of optically pure 2-substituted 1,3-propanediol derivatives and asymmetric synthesis of chroman ring and side chain of .alpha.-tocopherol
  作者：Toshiro Harada、Toshio Hayashiya、Isao Wada、Naoko Iwaake、Akira Oku

  DOI：10.1021/ja00236a034

  日期：1987.1
• 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.