(2R*,3S*)-2-Ethylhexan-1,3-diol

• 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: (2R*,3S*)-2-Ethylhexan-1,3-diol
• 英文别名: (2R,3S)-2-ethylhexane-1,3-diol
• 化学式: C₈H₁₈O₂
• 分子量: 146.23
• InChiKey: RWLALWYNXFYRGW-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  5
• 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：

  2,2-二甲氧基丙烷 、 (2R*,3S*)-2-Ethylhexan-1,3-diol 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 2.5h， 生成 (4R)-5-ethyl-2,2-dimethyl-4-propyl-1,3-dioxane
  参考文献：
  名称：

  通过体外定向进化完全转变醛缩酶的反应特异性：通用脂肪族醛缩产物的合成

  摘要：

  对果糖-6-磷酸醛缩酶进行了结构引导工程，以将其底物混杂性扩展到脂肪族亲核试剂，即未取代的烷酮和烷醛。创建了一个针对残基 D6、T26 和 N28 的“智能”组合文库，这些残基在亲核碳原子周围形成结合袋。通过高性能薄层色谱法进行双选择性筛选，可以同时测定总活性以及优先选择丙酮与丙醛作为竞争亲核试剂。D6 被证明是能够与非羟基化亲核试剂发生反应的关键残基。总共发现了 25 个单位点和双位点变体（D6X 和 D6X/T26X），它们表现出有用的合成活性，并且对酮或醛作为羟醛亲核试剂具有不同的偏好。值得注意的是，所有新变体都完全失去了裂解 6-磷酸果糖的天然活性。

  DOI：

  10.1002/anie.201804831
• 作为产物：
  描述：

  2-ethyl-1-hydroxy-3-hexanone 在 sodium hydroxide 、 双氧水 、 lithium hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 36.67h， 生成 (2R*,3S*)-2-Ethylhexan-1,3-diol
  参考文献：
  名称：

  The Role of theα-Stereogenic Center in the Control of Stereoselection in the Reduction ofα-Alkyl-β-hydroxy Ketones: A Highly Diastereoselective Protocol for the Synthesis of 1,2-syn-2-Alkyl-1,3-diols

  摘要：

  Accurate investigations on the role played by an alpha-stereogenic center in controlling the reduction of various classes of beta-hydroxy ketones allowed us to set up a general and highly diastereoselective protocol for the synthesis of 2-alkyl-1,3-diols with 1,2-syn relationship. This methodology is based on the conversion of a beta-hydroxy ketone into the corresponding titanium alcoholate that permits us to organize the substrate in a stable and rigid structure, which stereofacially favors attacking hydride ions. The use of THF as solvent makes available a variety of hydride donors that cover a large spectrum of steric demand: the choice of the more appropriate one depends on the conformational stability of the cyclic intermediate. Excellent results are obtained also in the presence of an additional stereogenic center in the beta-position, even if it exerts a concordant or an opposite steric effect with respect to the alpha-substituent.

  DOI：

  10.1002/1521-3765(20000717)6:14<2590::aid-chem2590>3.0.co;2-x

文献信息

• Asymmetric cross- and self-aldol reactions of aldehydes in water with a polystyrene-supported triazolylproline organocatalyst
  作者：Patricia Llanes、Sonia Sayalero、Carles Rodríguez-Escrich、Miquel A. Pericàs

  DOI：10.1039/c6gc00792a

  日期：——

  A polystyrene-immobilized triazolylproline has been prepared by a bottom-up approach involving co-polymerization with full regiocontrol. The resulting PS resin swells in water and has been applied to the enantioselective cross-aldol...

  聚苯乙烯固定的三唑基脯氨酸是通过自下而上的方法制备的，该方法涉及共聚合和完全区域控制。所得的PS树脂在水中溶胀，并已应用于对映选择性交叉醇醛树脂。
• The Role of theα-Stereogenic Center in the Control of Stereoselection in the Reduction ofα-Alkyl-β-hydroxy Ketones: A Highly Diastereoselective Protocol for the Synthesis of 1,2-syn-2-Alkyl-1,3-diols
  作者：Giuseppe Bartoli、Maria C. Bellucci、Marcella Bosco、Renato Dalpozzo、Enrico Marcantoni、Letizia Sambri

  DOI：10.1002/1521-3765(20000717)6:14<2590::aid-chem2590>3.0.co;2-x

  日期：2000.7.17

  Accurate investigations on the role played by an alpha-stereogenic center in controlling the reduction of various classes of beta-hydroxy ketones allowed us to set up a general and highly diastereoselective protocol for the synthesis of 2-alkyl-1,3-diols with 1,2-syn relationship. This methodology is based on the conversion of a beta-hydroxy ketone into the corresponding titanium alcoholate that permits us to organize the substrate in a stable and rigid structure, which stereofacially favors attacking hydride ions. The use of THF as solvent makes available a variety of hydride donors that cover a large spectrum of steric demand: the choice of the more appropriate one depends on the conformational stability of the cyclic intermediate. Excellent results are obtained also in the presence of an additional stereogenic center in the beta-position, even if it exerts a concordant or an opposite steric effect with respect to the alpha-substituent.
• Complete Switch of Reaction Specificity of an Aldolase by Directed Evolution In Vitro: Synthesis of Generic Aliphatic Aldol Products
  作者：Sebastian Junker、Raquel Roldan、Henk-Jan Joosten、Pere Clapés、Wolf-Dieter Fessner

  DOI：10.1002/anie.201804831

  日期：2018.8.6

  as competing nucleophiles. D6 turned out to be the key residue that enabled activity with non‐hydroxylated nucleophiles. Altogether 25 single‐ and double‐site variants (D6X and D6X/T26X) were discovered that show useful synthetic activity and a varying preference for ketone or aldehyde as the aldol nucleophiles. Remarkably, all of the novel variants had completely lost their native activity for cleavage

  对果糖-6-磷酸醛缩酶进行了结构引导工程，以将其底物混杂性扩展到脂肪族亲核试剂，即未取代的烷酮和烷醛。创建了一个针对残基 D6、T26 和 N28 的“智能”组合文库，这些残基在亲核碳原子周围形成结合袋。通过高性能薄层色谱法进行双选择性筛选，可以同时测定总活性以及优先选择丙酮与丙醛作为竞争亲核试剂。D6 被证明是能够与非羟基化亲核试剂发生反应的关键残基。总共发现了 25 个单位点和双位点变体（D6X 和 D6X/T26X），它们表现出有用的合成活性，并且对酮或醛作为羟醛亲核试剂具有不同的偏好。值得注意的是，所有新变体都完全失去了裂解 6-磷酸果糖的天然活性。