Benzoesaeure<(R)-3-hydroxybutyl>ester | 82598-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoesaeure<(R)-3-hydroxybutyl>ester
• 英文别名: (R)-(-)-1,3-butanediol 1-benzoate；(3R)-1-benzoyloxy-3-butanol；(R)-3-hydroxybutyl benzoate；(3R)-butan-3-ol-1-benzoate；Benzoesaeure((R)-3-hydroxybutyl)ester；1,3-Butanediol, 1-benzoate, (3R)-；[(3R)-3-hydroxybutyl] benzoate
• CAS: 82598-19-4
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: ZLYDSUAKIPQLNA-SECBINFHSA-N

物化性质

• 沸点：
  318.6±25.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzoesaeure<(R)-3-hydroxybutyl>ester 在 咪唑 、 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(S)-3-bromobutyl benzoate
  参考文献：
  名称：

  通过 Pd 催化的氧化还原级联直接 β-烷基化酮和醛

  摘要：

  我们报告了通过 Pd 催化的氧化还原级联策略用简单的烷基溴对酮和醛进行直接 β-烷基化。铜助催化剂的使用对于提高效率很重要。该反应是氧化还原中性的，不需要强酸或强碱。环状和无环酮以及α-支化醛都是与仲和叔烷基溴偶联的合适底物。Zanapezil 的简明正式合成是使用这种 β-烷基化方法实现的。

  DOI：

  10.1021/jacs.8b03530
• 作为产物：
  描述：

  Benzoic acid (R)-3-(tetrahydro-pyran-2-yloxy)-butyl ester 在 甲醇 、 4-甲基苯磺酸吡啶 作用下， 反应 3.0h， 以56%的产率得到Benzoesaeure<(R)-3-hydroxybutyl>ester
  参考文献：
  名称：

  Asymmetric Addition of an Electrophile to Naphthalenes Promoted and Stereodirected by Alcohol

  摘要：

  4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) reacts with 1 -methoxy-4-methylnaphthalene to give the 1,4-addition product in the presence of methanol; the reaction does not proceed in the absence of the alcohol. Methoxy exchange (with CD3OD) was also observed during the reaction. Reactions of PTAD with 1-(3-hydroxypropoxy)-4-methylnaphthalene and related naphthalenes afford stereoselectively 1,4-adducts (70-98% of the major diastereomer). The stereoface-selective addition of PTAD at C-4 with concurrent formation of an acetal at C-1 takes place in a syn manner, which is induced by the hydrogen-bonding interaction between PTAD and the hydroxy group. The alpha -methyl substitution on the propoxy side chain strongly enhances the stereodifferentiation (90% de) and accelerates the cyclization by the Thorpe-Ingold effect. The alkoxy moiety of the adduct is easily removed to give 4-methyl-4-amino-4H-naphthalen-1-one with high enantiomeric excess. The gamma -methyl group of the side chain also affects the stereodifferentiation. Thus, the two stereogenic centers of the (1S,3R)-3-hydroxy-1-methylbutoxy side chain work together to achieve the high stereodifferentiating 1,4-addition from the Si-Re face (up to 96% ee). Epimerization of the cyclic acetal of a minor adduct was observed during the reaction of 1-(3-hydroxybutoxy)-4-methylnaphthalene, indicating that the minor component of the final products is derived from the initial minor syn adduct formed from the opposite face. The syn selectivity of the addition is achieved completely in the initial stage of formation of both the major and the minor adducts.

  DOI：

  10.1021/ja0029477

文献信息

• Über die Depolymerisierung von Poly-(<i>R</i>)-3-hydroxy-buttersäureester (<i>PHB</i>)
  作者：Dieter Seebach、Max Züger

  DOI：10.1002/hlca.19820650208

  日期：1982.3.17

  On the Depolymerization of Poly-(R)-3-hydroxy-butanoate (PHB)

  关于聚（R）-3-羟基丁酸酯（PHB）的解聚
• Total Synthesis of Macrosphelide M from Diacetone Glucose
  作者：Gangavaram V. M. Sharma、Post Sai Reddy

  DOI：10.1002/ejoc.201101603

  日期：2012.4

  The total synthesis of macrosphelide M is described. The key steps include the preparation of the acid and alcohol fragments from diacetone glucose and (S)-malic acid, respectively, followed by Yamaguchi esterification and macrocyclization of the tris-olefin by ring-closing metathesis. Finally, one-pot deprotection of the PMB and TBS groups with TiCl4 results in the target. The C-3/C-4 stereocenters

  描述了 macrosphelide M 的全合成。关键步骤包括分别从双丙酮葡萄糖和 (S)-苹果酸制备酸和醇片段，然后通过闭环复分解对三烯烃进行山口酯化和大环化。最后，用 TiCl4 对 PMB 和 TBS 基团进行一锅法脱保护，得到目标。双丙酮葡萄糖的 C-3/C-4 立体中心用于引入四个立体中心，而第五个立体中心由 (S)-苹果酸实现。
• Stereoselective synthesis of ophiocerin B
  作者：Bhasker Akkala、Krishna Damera

  DOI：10.3998/ark.5550190.p007.986

  日期：——

  A stereoselective total synthesis of ophiocerin B is reported by asymmetric synthesis, starting from L-malic acid. Of the three stereogenic centers, the vic-diols C-3, C-4 were obtained by Sharpless asymmetric dihydroxylation.

  通过不对称合成，从 L-苹果酸开始，报道了 ophiocerin B 的立体选择性全合成。在三个立体中心中，vic-二醇 C-3、C-4 是通过 Sharpless 不对称二羟基化获得的。
• Stereospecific synthesis of secondary amines by the Mitsunobu reaction
  作者：Michael L. Edwards、David M. Stemerick、James R. McCarthy

  DOI：10.1016/s0040-4039(00)97411-2

  日期：1990.1
• Use of the Mitsunobu reaction in the synthesis of polyamines
  作者：Michael L. Edwards、David M. Stemerick、James R. McCarthy

  DOI：10.1016/s0040-4020(01)85630-1

  日期：1994.1

  The Mitsunobu reaction has been used in the synthesis of polyamine analogues. The synthesis of the (R,R), (S,S) and meso- isomers of a tetraamine are described. The chemistry was used to synthesize a fluorinated polyamine analog and a hexaamine.