(2R)-acetic acid 3-hydroxy-2-methyl-propyl ester | 119786-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-acetic acid 3-hydroxy-2-methyl-propyl ester
• 英文别名: (R)-3-hydroxy-2-methylpropyl acetate；(R)-3-acetoxy-2-methyl-1-propanol；[(2R)-3-hydroxy-2-methylpropyl] acetate
• CAS: 119786-13-9
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: IYAIBVKPRAZUDT-RXMQYKEDSA-N

物化性质

• 沸点：
  142.6±13.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (2R)-acetic acid 3-hydroxy-2-methyl-propyl ester 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以45%的产率得到(-)-(S)-3-(acetyloxy)-2-methylpropanoic acid
  参考文献：
  名称：

  An easy route to 4-substituted 2-oxazolidinones from prochiral-1,3-diols

  摘要：

  A novel synthesis of 4-substituted 2-oxazolidniones starting from prochiral-1,3-diols has been developed. After enzymatic desymmetrisation the resulting monoacetyled diols were transformed into amides. A Hofmann rearrangement of these amides led to 2-oxazolidinones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.034
• 作为产物：
  描述：

  (+/-)-3-(4-methoxybenzyloxy)-2-methylpropyl acetate 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 丙酮 为溶剂， 反应 48.5h， 生成 (2R)-acetic acid 3-hydroxy-2-methyl-propyl ester
  参考文献：
  名称：

  Stereo flexible synthesis of the C8–C23 fragment of antarlides, androgen receptor antagonists

  摘要：

  By combining enzymatic and chemical processes, we achieve stereo-flexible synthesis of a key C8–C23 fragment shared among all antarlides which are androgen receptor antagonists.

  DOI：

  10.1039/d4ob00852a

文献信息

• Chemoenzymatic Asymmetric Total Synthesis of Nonanolide (<i>Z</i>)-Cytospolides D, E and Their Stereoisomers
  作者：Rohan Kalyan Rej、Samik Nanda

  DOI：10.1002/ejoc.201301365

  日期：2014.2

  asymmetric total synthesis of the (Z)-isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring-closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was accessed by two

  据报道，天然存在的癸内酯细胞质 D、E 和六种立体异构体的 (Z)-异构体的化学酶不对称全合成。该合成企业的主要亮点涉及适当官能化的酯化合物的闭环复分解 (RCM) 反应，该反应通过所需的酸和醇片段的 Yamaguchi 偶联组装而成。醇片段通过两种替代的化学酶促过程获得，一种是羟腈裂解酶介导的氢氰化，而脂肪酶催化的酯交换是第二种途径中的关键 sep。酸片段是通过前手性 2-甲基-1,3-丙二醇和 Corey-Bakshi-Shibata (CBS) 介导的立体选择性羰基还原的对映选择性酶解对称 (EED) 构建的。
• Tunable <i>P</i>-Chiral Bisdihydrobenzooxaphosphole Ligands for Enantioselective Hydroformylation
  作者：Renchang Tan、Xin Zheng、Bo Qu、C. Avery Sader、Keith R. Fandrick、Chris H. Senanayake、Xumu Zhang

  DOI：10.1021/acs.orglett.6b01452

  日期：2016.7.15

  Air-stable and tunable chiral bisdihydrobenzooxaphosphole ligands (BIBOPs) were employed in rhodium-catalyzed asymmetric hydroformylation of various terminal olefins with excellent conversions (>99%), moderate-to-excellent enantioselectivities (up to 95:5 er), and branched to linear ratios (b:l) of up to 400.

  空气稳定且可调的手性双二氢苯并恶唑磷配体（BIBOP）用于铑催化的各种末端烯烃的不对称加氢甲酰化反应，具有出色的转化率（> 99％），中等至优异的对映选择性（高达95：5 er），并分支为线性比（b：l）高达400。
• Lipase-catalyzed asymmetric synthesis of chiral 1,3-propanediols and its application to the preparation of optically pure building block for renin inhibitors
  作者：Keiichiro Tsuji、Yoshiyasu Terao、Kazuo Achiwa

  DOI：10.1016/s0040-4039(01)93338-6

  日期：——

  Asymmetric synthesis of chiral 2-substituted-1,3-propanediols was realized by the lipase-catalyzed transesterification in vinyl acetate and it was applied to the synthesis of an optically active sulfone derivative.

  通过在乙酸乙烯酯中的脂肪酶催化的酯交换反应实现了手性2-取代-1,3-丙二醇的不对称合成，并将其用于旋光砜衍生物的合成。
• Chemo-enzymatic synthesis of the C₁₅–C₂₃unit of Leptomycin B
  作者：Michael Scheck、Herbert Waldmann

  DOI：10.1139/v02-070

  日期：2002.6.1

  The asymmetric synthesis of the C₁₅–C₂₃unit of Leptomycin B (LMB) is described. All four stereocenters of the C₁₅–C₂₃unit were prepared from one building block exhibiting only one stereocenter. This building block was synthesized via either an enzymatic transformation or starting from a chiral reagent.Key words: Leptomycin, natural product synthesis, enzymatic transformation, Aldol reaction, Pseudomonas fluorescence lipase (PFL).

  描述了Leptomycin B（LMB）的C₁₅–C₂₃单元的不对称合成。 C₁₅–C₂₃单元的四个立体中心均由一个仅具有一个立体中心的构建块制备而成。 该构建块通过酶转化或从手性试剂出发合成。关键词：Leptomycin，天然产物合成，酶转化，Aldol反应，假单胞菌荧光素酶（PFL）。
• A facile synthesis of (–)-muscone using a chemo-enzymatic approach
  作者：Zhuo-Feng Xie、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1039/c39880001638

  日期：——

  Pseudomonas fluorescens lipase catalysed hydrolysis of the meso-diacetate (1) to give specifically the (R)-enantiomer (2) with high optical purity allows the synthesis of (–)-muscone in combination with a three-carbon ring expansion.

  荧光假单胞菌脂肪酶催化内消旋二乙酸酯（1）水解，得到具有高光学纯度的（R）-对映异构体（2），可以合成（-）-muscone和三碳环扩环。