DL-4-氯-3-羟基丁酸乙酯 | 10488-69-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: DL-4-氯-3-羟基丁酸乙酯
• 中文别名: 4-氯-3-羟基丁酸乙酯；S(-)-4-氯-3-羟基丁酸乙酯；S-4-氯-3-羟基丁酸乙酯；ATS-4；(S)-4-氯-3-羟基丁酸乙酯；S-4-氯-3-羟基丁酸乙脂；(R,S)4-氯-3-羟基丁酸乙酯；COBE
• 英文名称: ethyl 4-chloro-3-hydroxybutanoate
• 英文别名: 4-chloro-3-hydroxybutyric acid ethyl ester；ethyl (+/-)-4-chloro-3-hydroxybutanoate；rac-ethyl 4-chloro-3-hydroxybutanoate；ethyl 3-hydroxy-4-chlorobutyrate；ethyl 4-chloro-3-hydroxybutyrate；4-chloro-3-hydroxybutanoate
• CAS: 10488-69-4
• 化学式: C₆H₁₁ClO₃
• mdl: MFCD09839767
• 分子量: 166.605
• InChiKey: ZAJNMXDBJKCCAT-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  155-157 °C(Press: 10 Torr)
• 密度：
  1.1257 g/cm3(Temp: 16 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090
• 危险品标志：
  Xi
• 危险类别码：
  R41
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P273,P280,P305+P351+P338+P310,P312,P501
• 危险品运输编号：
  3082
• 危险性描述：
  H302,H318,H401
• 安全说明：
  S26,S39
• 储存条件：
  室温

制备方法与用途

奥拉西坦中间体

反应信息

• 作为反应物：
  描述：

  DL-4-氯-3-羟基丁酸乙酯 生成 S(-)-4-氯-3-羟基丁酸乙酯
  参考文献：
  名称：

  A novel generation of optically active ethyl 4-chloro-3-hydroxybutyrate as a C4 chiral building unit using microbial dechlorination

  摘要：

  A novel procedure for the generation of optically active ethyl 4-chloro-3-hydroxybutyrate using bacterial cells was developed. Ethyl (S)-4-chloro-3-hydroxybutyrate was prepared by Pseudomonas sp. OS-K-29, which stereoselectively assimilates 2,3-dichloro-1-propanol. The reaction was based on its kinetic dehalogenation for both enantiomers using the resting cells. The obtained 4-chloro-3-hydroxybutyrate rate had high enantiomeric excess of >98%, with a yield of 33% at the microbial resolution step. Moreover, several C4 compounds having the 4-chloro-3-hydroxyl function were also resolved and gave good enantiomeric purities (>95 %ee). Ethyl (R)-4-chloro-3-hydroxybutyrate was also obtained with high enantiomeric purity (>98 %ee) using the cells of Pseudomonas sp DS-K-NR818. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00410-7
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 在 Ru((S)-biaryl diphosphine)Cl₂(DMF)n 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 70.0 ℃ 、344.75 kPa 条件下， 反应 24.0h， 生成 DL-4-氯-3-羟基丁酸乙酯
  参考文献：
  名称：

  新型非对映体二膦配体的合成及其在不对称氢化反应中的应用。

  摘要：

  ［结构：见正文］合成了在主链上增加了手性中心的非对映体联芳基二膦配体10和11。在非对映体二膦氧化物的制备的偶联步骤中发生了底物定向的不对称合成。通过使用硅胶的柱色谱法容易地分离非对映体二膦氧化物。含有这些配体的钌催化剂在2-（6'-甲氧基-2'-萘基）丙酸和β-酮酸酯的氢化中非常有效。额外的手性中心对催化剂的对映选择性和活性有重大影响。

  DOI：

  10.1021/ol026817+

文献信息

• Structure elucidation of pantherine, a flycidal alkaloid from Amanita pantherina (DC.) Fr.
  作者：YAEKO KONDA、HIROSHI TAKAHASHI、MASAYUKI ONDA

  DOI：10.1248/cpb.33.1083

  日期：——

  Pantherine is identified as 5-aminomethyl-3-hydroxyisoxazole by means of spectroscopic experiments and chemical correlation with synthetic compounds.

  通过光谱实验及与合成化合物的化学关联，鉴定出Pantherine为5-氨基甲基-3-羟基异恶唑。
• Process for the preparation of 3-hydroxytetrahydrofuran
  申请人：Kaneka Corporation

  公开号：US06359155B1

  公开（公告）日：2002-03-19

  An industrial advantage process for producing high-purity 3-hydroxytetrahydrofuran easily and simply, which comprises reducing a 4-halo-3-hydroxybutyric acid ester (1) with a boron hydride compound and/or an aluminum hydride compound as a reducing agent in an organic solvent immiscible with water; treating the reaction mixture with an acid and water to thereby effect conversion to the corresponding 4-halo-1,3-butanediol and at the same time giving an aqueous solution containing said compound; carrying out the cyclization reaction of the 4-halo-1,3-butanediol in said aqueous solution; extracting the resulting 3-hydroxytetrahydrofuran from the 3-hydroxytetrahydrofuran-containing aqueous solution using an organic solvent immiscible with water; and isolating the 3-hydroxytetrahydrofuran by concentration and/or distillation of the solution obtained.

  一种用于轻松简便地生产高纯度3-羟基四氢呋喃的工业优势工艺，包括在一种与水不相溶的有机溶剂中，将4-卤代-3-羟基丁酸酯（1）用硼氢化合物和/或铝氢化合物作为还原剂还原；用酸和水处理反应混合物，从而使其转化为相应的4-卤代-1,3-丁二醇，同时给出含有该化合物的水溶液；在所述水溶液中进行4-卤代-1,3-丁二醇的环化反应；使用一种与水不相溶的有机溶剂从含有3-羟基四氢呋喃的水溶液中提取所得的3-羟基四氢呋喃；通过浓缩和/或蒸馏所得溶液来分离3-羟基四氢呋喃。
• Practical Syntheses of (S)-4-Hydroxytetrahydrofuran-2-one, (S)-3-Hydroxytetrahydrofuran and Their (R)-Enantiomers
  作者：Yoshifumi Yuasa、Haruki Tsuruta

  DOI：10.1002/jlac.199719970911

  日期：1997.9

  Optically active 4-hydroxytetrahydrofuran-2-one (3) has been synthesized in good yield from optically active ethyl 4-chloro-3-hydroxybutanoate (2) by refluxing with dilute hydrochloric acid. In a similar manner, optically active 3-hydroxytetrahydrofuran (5) was prepared from optically active 4-chloro-1,3-butanediol (4), which was derived from 2 by NaBH4 reduction. These new cyclizations proceed without

  光学活性的4-羟基四氢呋喃-2-酮（3）是由光学活性的4-氯-3-羟基丁酸乙酯（2）通过与稀盐酸回流而合成的。以类似的方式，由旋光的4-氯-1，3-丁二醇（4）制备旋光的3-羟基四氢呋喃（5），所述旋光的4-氯-1，3-丁二醇（2）通过NaBH 4还原而从2中衍生。这些新的环化反应没有消旋作用。
• Strain‐Release Driven Spirocyclization of Azabicyclo[1.1.0]butyl Ketones
  作者：Jasper L. Tyler、Adam Noble、Varinder K. Aggarwal

  DOI：10.1002/anie.202102754

  日期：2021.5.17

  engage in electrophile‐induced spirocyclization‐desilylation reactions. Primary, secondary and tertiary silyl ethers were effectively transformed into a library of new spiro‐azetidines, with a range of substituents and ring sizes. In addition, the products are generated with synthetically useful ketone and protected‐amine functional groups, which provides the potential for further elaboration and for

  由于其固有的刚性、三维性和结构新颖性，螺环分子已成为药物发现中越来越受欢迎的部分。在此，我们报告了通过利用氮杂双环[1.1.0]丁烷（ABB）片段的固有环应变，以应变释放驱动合成含氮杂环丁烷的螺环。一步合成了带有甲硅烷基保护醇的新型 ABB 酮前体，并显示其参与亲电试剂诱导的螺环化-脱甲硅烷化反应。伯、仲和叔硅醚被有效地转化为具有一系列取代基和环尺寸的新型螺氮杂环丁烷库。此外，这些产品是用合成有用的酮和受保护的胺官能团生成的，这为进一步阐述以及将这种化学用于快速组装医学相关化合物提供了潜力。
• Stereoselective Enzymatic Synthesis of Chiral Alcohols with the Use of a Carbonyl Reductase from <i>Candida </i><i>m</i><i>agnoliae</i> with Anti-Prelog Enantioselectivity
  作者：Dunming Zhu、Yan Yang、Ling Hua

  DOI：10.1021/jo0603328

  日期：2006.5.1

  carbonyl reductases with anti-Prelog enantioselectivity, the activity and enantioselectivity of a carbonyl reductase from Candida magnoliae have been examined with various ketones of diverse structures. This carbonyl reductase catalyzed the reduction of a series of ketones, α- and β-ketoesters, to anti-Prelog configurated alcohols in excellent optical purity. The usefulness of this carbonyl reductase has

  在我们努力寻找具有抗Prelog对映选择性的羰基还原酶的过程中，已经用各种结构不同的酮检查了来自白色假丝酵母的羰基还原酶的活性和对映选择性。这种羰基还原酶催化将一系列酮（α-和β-酮酸酯）还原为具有出色光学纯度的抗Prelog构型醇。该羰基还原酶的有用性已通过几种具有药学重要性的手性醇中间体的合成得到证明。