2-氯-3-羟基-3-苯基丙酸乙酯 | 29782-09-0

• 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: 2-氯-3-羟基-3-苯基丙酸乙酯
• 英文名称: ethyl anti-2-chloro-3-hydroxy-3-phenylpropanoate
• 英文别名: ethyl 2-chloro-3-hydroxy-3-phenylpropanoate；ethyl 2-chloro-3-hydroxy-3-phenylpropionate；(2RS,3RS)-2-chloro-3-hydroxy-3-phenyl-propionic acid ethyl ester；(2RS,3RS)-2-Chlor-3-hydroxy-3-phenyl-propionsaeure-aethylester；ethyl (2S,3S)-2-chloro-3-hydroxy-3-phenylpropanoate
• CAS: 29782-09-0；29782-10-3；88624-60-6；146452-39-3；146452-40-6
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: OHWTWQBFVOCYOY-UWVGGRQHSA-N

物化性质

• 熔点：
  72 °C(Solv: ligroine (8032-32-4))
• 沸点：
  165 °C(Press: 4 Torr)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 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：

  2-氯-3-羟基-3-苯基丙酸乙酯 在 indium(III) chloride 、 indium 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以75%的产率得到反式-肉桂酸乙酯
  参考文献：
  名称：

  Indium-Mediated Reductive Elimination of Halohydrins

  摘要：

  Olefin formation has been successfully carried out by reductive elimination reactions of halohydrins with Pd(PPh3)(4)/In/InCl3 in aqueous media.

  DOI：

  10.1021/jo0262964
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 2-氯-3-羟基-3-苯基丙酸乙酯
  参考文献：
  名称：

  GigaE PM: a high performance communication facility using a Gigabit Ethernet

  摘要：

  A high performance communication facility, called the GigaE PM, has been designed and implemented for parallel applications on clusters of computers using a Gigabit Ethernet. The GigaE PM provides not only a reliable high bandwidth and low latency communication, but also supports existing network protocols such as TCP/IP. A reliable communication mechanism for a parallel application is implemented on the firmware on a NIC while existing network protocols are handled by an operating system kernel. A prototype system has been implemented using an Essential Communications Gigabit Ethernet card. The performance results show that a 58.3 mu s round trip time for a four byte user message, Emd 56.7 MBytes/sec bandwidth for a 1,468 byte message have been achieved on Intel Pentium II 400 MHz PCs. We have implemented MPICH-PM on top of the GigaE PM, and evaluated the NAS parallel benchmark performance. The results show that the IS class S performance on the GigaE PM is 1.8 times faster than that on TCP/IP.

  DOI：

  10.1007/bf03037596

文献信息

• A NOVEL METHOD FOR THE GENERATION OF AN ESTER ENOLATE ANION FROM ETHOXYACETYLENE
  作者：Teruaki Mukaiyama、Masahiro Murakami

  DOI：10.1246/cl.1981.1129

  日期：1981.8.5

  An ester enolate anion was generated in situ by the successive treatment of ethoxyacetylene with mercury(II) chloride, pyridine-1-oxide and zinc dust, and the zinc enolate thus formed further reacted with aldehydes to give α-chloro-β-hydroxyesters.

  通过用氯化汞 (II)、吡啶-1-氧化物和锌粉连续处理乙氧基乙炔，原位生成酯烯醇阴离子，由此形成的烯醇锌进一步与醛反应生成α-氯-β-羟基酯。
• Synthesis of (2<i>S</i>)-2-Chloro-2-fluororibolactone via Stereoselective Electrophilic Fluorination
  作者：Coralie De Schutter、Ozkan Sari、Steven J. Coats、Franck Amblard、Raymond F. Schinazi

  DOI：10.1021/acs.joc.7b02245

  日期：2017.12.15

  A novel and efficient route for the preparation of (2S)-2-chloro-2-fluorolactone 29 is described. This approach takes advantage of a highly efficient diastereoselective electrophilic fluorination reaction (94% yield; >50:1 dr)

  描述了一种新颖且有效的制备（2 S）-2-氯-2-氟内酯29的途径。这种方法利用了高效的非对映选择性亲电子氟化反应（94％的收率；> 50：1 dr）
• A new dehydrogenase from Clostridium acetobutylicum for asymmetric synthesis: dynamic reductive kinetic resolution entry into the Taxotère side chain
  作者：Gregory A. Applegate、Ross W. Cheloha、David L. Nelson、David B. Berkowitz

  DOI：10.1039/c0cc04585c

  日期：——

  has been expressed and characterized. CaADH enantioselectively reduces aromatic alpha-, beta- and gamma-keto esters to the corresponding D-hydroxy esters and provides a building block for the Taxotere side chain (95% yield, 95% de, 99% ee) by dynamic reductive kinetic resolution (DYRKR).

  来自丙酮丁醇梭菌 (CaADH) 的 NADP 依赖性乙醇脱氢酶已得到表达和表征。 CaADH 对映选择性地将芳香族 α-、β- 和 γ-酮酯还原为相应的 D-羟基酯，并通过动态还原动力学拆分为泰索帝侧链提供构建模块（产率 95%，de 95%，ee 99%）（迪尔克）。
• Asymmetric Reduction of 2-Chloro-3-oxo Esters by Transfer Hydrogenation
  作者：Jinjin Bai、Shifeng Miao、Yun Wu、Yawen Zhang

  DOI：10.1002/cjoc.201180419

  日期：2011.11

  Asymmetric reduction of 2‐chloro‐3‐oxo esters was achieved by catalytic transfer hydrogenation using [RuCl2(p‐cymene)](S,S)‐TsDPEN as the chiral catalyst and HCOOH‐Et3N as the hydrogen source. Moderate to good yields (up to 85%) and good enantioselectivities (up to 98% ee) were obtained.

  通过使用[RuCl 2（p- cymene）]（S，S）-TsDPEN作为手性催化剂和HCOOH-Et 3 N作为氢源进行催化转移氢化，可以实现2-氯-3-氧代酸酯的不对称还原。获得了中等至良好的产率（高达85％）和良好的对映选择性（高达98％ee）。
• Biocatalytic dynamic reductive kinetic resolution of aryl α-chloro β-keto esters: divergent, stereocontrolled synthesis of diltiazem, clentiazem, and siratiazem
  作者：Xiaoping Yue、Yitong Li、Minjie Liu、Di Sang、Zedu Huang、Fener Chen

  DOI：10.1039/d2cc03102g

  日期：——

  of 100 g L−1 of substrate 6b at a ten-gram scale was achieved with a continuous fed-batch strategy, affording anti-(2S,3S)-1b, the key intermediate of diltiazem, in a record-breaking space-time yield of 96 g L−1 d−1. An eight-step synthesis of diltiazem, clentiazem, and siratiazem was accomplished in 32–45% overall yields, featuring this versatile biocatalytic reduction reaction as well as an efficient

  对芳基 α-氯 β-酮酯进行酮还原酶 (KRED) 催化的动态还原动力学拆分 (DYRKR) 的首次系统研究，并在 74– 98% 的分离产率，以及中等至优异的非对映选择性（高达 >99 : 1 dr）和良好至优异的对映选择性（大部分 >99% ee）。LfSDR1 催化完全还原 10 克规模的 100 g L -1底物6b是通过连续补料分批策略实现的，在破纪录的时空产量 96 g L -1 d -1. 地尔硫卓、克林特西姆和西拉硫卓的八步合成以 32-45% 的总收率完成，具有这种多功能的生物催化还原反应以及高效、绿色的流动氯化反应。