(+)(S)-2,3,3-trimethyl-1-butanol | 54712-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)(S)-2,3,3-trimethyl-1-butanol
• 英文别名: (S)-2,3,3-trimethyl-1-butanol；(S)-2,3,3-trimethylbutan-1-ol；2,3,3-trimethyl-1-butanol；(S)-2,3,3-trimethyl-butan-1-ol；(+)-(S)-2,3,3-Trimethylbutan-1-ol；(2S)-2,3,3-Trimethylbutan-1-OL
• CAS: 54712-26-4
• 化学式: C₇H₁₆O
• 分子量: 116.203
• InChiKey: IWWVOLGZHKFWKK-ZCFIWIBFSA-N

物化性质

• 沸点：
  138.3±8.0 °C(Predicted)
• 密度：
  0.818±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)(S)-2,3,3-trimethyl-1-butanol 在 吡啶 、 氯化亚砜 作用下， 生成 (+)-(R)-3,4,4-trimethylpentanoic acid
  参考文献：
  名称：

  Giacomelli,G. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1795 - 1798

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,3-trimethylbutan-1-ol 在 Pseudomonas cepacia lipase 、 三乙胺 作用下， 以 aq. phosphate buffer 、 异丙醇 为溶剂， 生成 (+)(S)-2,3,3-trimethyl-1-butanol
  参考文献：
  名称：

  A new mechanism of enantioselectivity toward chiral primary alcohol by lipase from Pseudomonas cepacia

  摘要：

  The stereo-recognition of chiral primary alcohols by lipase from Pseudomonas cepacia was found to deviate from earlier observations. Enantioselectivity toward 14 pairs of chiral primary alcohol esters by this lipase was dependent on the existence of an Onon-alpha (oxygen at non-alpha-position of the acyloxy group) in the alcohol moiety, and decreased as the size of the acyl moiety increased. Chemical modification on the lipase and molecular dynamics simulations indicated that Tyr(29) located within the catalytic cavity forms a hydrogen bond with the Onon-alpha of the preferred enantiomer of the primary alcohol ester. However, a larger acyl moiety suffered stronger hindrance from the catalytic cavity wall of the lipase, pushing the Onon-alpha away from Tyr(29), and thus weakening the stereo-recognition. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.08.014

文献信息

• A Very Mild and Chemoselective Oxidation of Alcohols to Carbonyl Compounds
  作者：Lidia De Luca、Giampaolo Giacomelli、Andrea Porcheddu

  DOI：10.1021/ol016501m

  日期：2001.9.1

  oxidation of primary alcohols and beta-amino alcohols to the corresponding aldehydes and alpha-amino aldehydes can be carried out at room temperature and in methylene chloride, using trichloroisocyanuric acid in the presence of catalytic TEMPO: aliphatic, benzylic, and allylic alcohols, and beta-amino alcohols are rapidly oxidized without no overoxidation to carboxylic acids. Secondary carbinols are slowly

  伯醇和β-氨基醇可在室温下和在二氯甲烷中使用三氯异氰尿酸在TEMPO催化下高效氧化为相应的醛和α-氨基醛：脂族，苄基和烯丙基醇，以及β-氨基醇被迅速氧化而不会过度氧化成羧酸。仲甲醇被缓慢氧化，因此反应具有高度的化学选择性。反应：见文字。
• Stereochemistry of the sn2′ displacement of chiral 1, 3-disubstituted bromoallenes to form chiral acetylenes
  作者：E.J. Corey、Neil W. Boaz

  DOI：10.1016/0040-4039(84)80007-6

  日期：——

  Optically active 1,3-disubstituted bromoallenes react with a variety of cuprate reagents preferentially in an SN2′ fashion with very high anti selectivity.

  光学活性的1,3-二取代的溴化亚丙烯优先以S N 2'的方式与多种铜酸盐试剂反应，并具有很高的抗选择性。
• CHEMICAL COMPOUNDS
  申请人：ASTRAZENECA AB

  公开号：US20140206700A1

  公开（公告）日：2014-07-24

  The invention concerns compounds of Formula (I) or pharmaceutically-acceptable salts thereof, wherein R 1 and R 2 have any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of cell proliferative disorders.

  这项发明涉及公式(I)的化合物或其药用盐，其中R1和R2具有在描述中定义的任何含义；它们的制备方法，含有它们的药物组合物以及它们在治疗细胞增殖性疾病中的用途。
• An Efficient Route to Alkyl Chlorides from Alcohols Using the Complex TCT/DMF
  作者：Lidia De Luca、Giampaolo Giacomelli、Andrea Porcheddu

  DOI：10.1021/ol017168p

  日期：2002.2.1

  [reaction: see text] Efficient conversion of alcohols and beta-amino alcohols to the corresponding chlorides (and bromides) can be carried out at room temperature in methylene chloride, using 2,4,6-trichloro[1,3,5]triazine and N,N-dimethyl formamide. This procedure can also be applied to optically active carbinols.

  [反应：见正文]醇和β-氨基醇高效转化为相应的氯化物（和溴化物）可以在室温下在二氯甲烷中使用2,4,6-三氯[1,3,5]三嗪和N，N-二甲基甲酰胺。该程序也可以应用于旋光甲醇。
• Nickel-catalyzed stereodifferentiating displacement reaction between prochiral 1-alkenes and optically active organoaluminium solvates.
  作者：Giampaolo Giacomelli、Luigi Bertero、Luciano Lardicci

  DOI：10.1016/0040-4039(81)80021-4

  日期：1981.1

  The displacement reaction between optically active AlBui3 solvates and vinylidene alkenes, in the presence of Ni(mesal)2, affords optically active trialkylalanes and hence, upon hydrolysis or oxidative procedure, alkanes or 1-alkanols.

  在Ni（mesal）2存在下，光学活性的AlBu i 3溶剂化物和亚乙烯基烯烃之间的置换反应提供了光学活性的三烷基丙氨酸，因此在水解或氧化过程中产生了烷烃或1-链烷醇。