(3RS,5RS)-2,4,6-trimethylpentane-3,5-diol | 113889-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3RS,5RS)-2,4,6-trimethylpentane-3,5-diol
• 英文别名: 2,4,6-Trimethyl-heptane-3R,5R-diol；(3R,5R)-2,4,6-trimethylheptane-3,5-diol
• CAS: 113889-53-5
• 化学式: C₁₀H₂₂O₂
• 分子量: 174.283
• InChiKey: UPIITWBUFQQTNX-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diisopropylsilanediyl bistriflate 、 (3RS,5RS)-2,4,6-trimethylpentane-3,5-diol 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到2,2-r-4-t-6-Tetraisopropyl-5-methyl-1,3-dioxa-2-silacyclohexane
  参考文献：
  名称：

  1,3-versus 1,2-Asymmetric induction in the reduction of β-hydroxy ketones by intramolecular hydrosilylation

  摘要：

  The role of 1,2-asymmetric induction has been investigated in the 1,3-anti-selective reduction of beta-hydroxy ketones via intramolecular hydrosilylation. For the alpha-methyl beta-hydroxy ketones 2a, 3a, the effect of the alpha-substituent is negligible except that it appears to reinforce 1,3-asymmetric induction. For the alpha-ethyl beta-hydroxy ketones 2b, 3b, 1,3-asymmetric induction is dominant but not overwhelming. The super-acid TfOH2+ B(OTf)4- has been used as a catalyst for the hydrosilylation giving, in one case, an improved result when compared with previous methodology.

  DOI：

  10.1039/p19910001383
• 作为产物：
  描述：

  2-甲基-3-戊酮 在 sodium tetrahydroborate 、 air 、 三丁基硼 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (3RS,5RS)-2,4,6-trimethylpentane-3,5-diol
  参考文献：
  名称：

  通过硼螯合物将β-羟基酮立体选择性还原为1,3-二醇的高选择性1,3-不对称诱导

  摘要：

  通过硼螯合物还原无环β-羟基酮可以实现高度选择性的不对称诱导。β羟基酮的治疗（1）用三丁基-或三- isobutylborane和依次用硼氢化钠，得到顺式-1,3-二醇（3在高度立体选择性的方式），Syn的-α取代-β-hydroxyketones（8）为也还原为仅生成syn，syn -1,3-二醇（9）。该反应进一步用于方便地制备3-脱氧己糖。

  DOI：

  10.1016/0040-4020(84)80006-x

文献信息

• Directed reduction of .beta.-hydroxy ketones employing tetramethylammonium triacetoxyborohydride
  作者：D. A. Evans、K. T. Chapman、E. M. Carreira

  DOI：10.1021/ja00219a035

  日期：1988.5

  The mild reducing agent tetramethylammonium triacetoxyborohydride reduces acyclic P-hydroxy ketones to their corresponding anti diols with high diastereoselectivity. a-Alkyl substitution does not significantly affect the stereoselectivity of these reductions. In all cases examined, good to excellent yields of diastereomerically homogeneous diols were obtained. The mechanism of these reductions involves

  温和的还原剂四甲基铵三乙酰氧基硼氢化物以高非对映选择性将无环 P-羟基酮还原为其相应的反二醇。α-烷基取代不会显着影响这些还原的立体选择性。在所有检查的情况下，都获得了良好到极好的非对映异构体均质二醇的产率。这些还原的机制涉及三乙酰氧基硼氢化物阴离子将乙酸盐与底物醇进行酸促进的配体交换。所得氢化物中间体，大概是烷氧基二乙酰氧基硼氢化物，还原近端 OH 0 OH OH 0 Me,NHB(OAc), Mew Me&OR - OR Me he
• The directed reduction of β-hydroxy ketones employing Me4NHB(OAc)3
  作者：David A. Evans、Kevin T. Chapman

  DOI：10.1016/s0040-4039(00)85367-8

  日期：1986.1

  The diastereoseiective reduction of a range of acyclic β-hydroxy ketones with triacetoxyborohydride is described. In all cases, the anti 1,3-diol diastereomer is the principal product (eq 1).

  描述了用三乙酰氧基硼氢化物对一系列无环β-羟基酮进行非对映选择性还原。在所有情况下，抗1,3-二醇非对映异构体都是主要产物（式1）。
• 1,2-anti diastereoselective reduction of 2-alkyl-3-hydroxy-ketones via their silyl ethers
  作者：R. Bloch、L. Gilbert、C. Girard

  DOI：10.1016/0040-4039(88)85324-3

  日期：1988.1

  T-butyldimethylsilyl ethers of a range of acyclic 2-alkyl-3-hydroxy-ketones are reduced with lithium aluminum hydride to give with a high 1,2-anti diastereoselective induction syn,anti or anti,anti 2-alkyl-1,3-diols.

  用氢化铝锂还原一系列无环2-烷基-3-羟基酮的叔丁基二甲基甲硅烷基醚，得到具有高1,2-抗非对映选择性诱导的顺，反或反2-烷基-1,3 -二醇。
• Simple Metal Alkoxides as Effective Catalysts for the Hetero-Aldol−Tishchenko Reaction
  作者：Cheryl M. Mascarenhas、Matthew O. Duffey、Shih-Yuan Liu、James P. Morken

  DOI：10.1021/ol990246c

  日期：1999.11.1

  [GRAPHICS]This paper reports the utility of simple metal alkoxides for the catalytic, stereoselective hetero-aldol-Tishchenko reaction (eq 1), Choice of metal alkoxide is crucial to achieving high efficiency and stereoselectivity, Whereas NaO-t-Bu is an effective catalyst, delivering one product in 68% yield and 99:1 stereoselection, Sm(O-i-Pr)(3) is less effective and delivers the same product in 42% yield with 4:1 stereoselection.
• Tandem Aldol−Tishchenko Reactions of Lithium Enolates:  A Highly Stereoselective Method for Diol and Triol Synthesis
  作者：Paul M. Bodnar、Jared T. Shaw、K. A. Woerpel

  DOI：10.1021/jo971012e

  日期：1997.8.1