2-chloroethyl 2-phenylpropanoate | 33662-99-6

• 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: 2-chloroethyl 2-phenylpropanoate
• 英文别名: 2-chloroethyl 2-phenylpropionate；Chloroethyl 2-phenylpropionate
• CAS: 33662-99-6
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: VEJDVWKNNFHLAM-UHFFFAOYSA-N

物化性质

• 沸点：
  298.3±15.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloroethyl 2-phenylpropanoate 在 水 作用下， 反应 12.0h， 生成 S-2-苯基丙酸
  参考文献：
  名称：

  Cross-Linked Crystals of Candida rugosa Lipase: Highly Efficient Catalysts for the Resolution of Chiral Esters

  摘要：

  To date, most enzyme-based organic syntheses have employed enzymes in the form. of a crude protein extract. The instability and expense of highly purified proteins has all but obviated their use as catalysts for enantioselective hydrolyses. Herein, we describe the use of the major hydrolase from commercial Candida rugosa lipase (CRL) in the form of a cross-linked enzyme crystal (CLEC) for the enantioselective hydrolysis of chiral racemic esters. The enantioselectivity of CRL-CLECs in the hydrolysis of many important chiral esters is vastly superior to that of the crude CRL extract. Since the CRL-CLEC is insoluble, recoverable, and 2-3 orders of magnitude more stable than the soluble protein, the CRL-CLEC is an attractive replacement for the crude enzyme preparation. The use of this catalyst in the resolution of chiral esters 1-11 and in the preparative scale (la):and multicycle resolution (2a) of important anti-inflammatory drugs is described.

  DOI：

  10.1021/ja00131a006
• 作为产物：
  描述：

  2-乙基-2-苯基-1,3-二氧戊环 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到2-chloroethyl 2-phenylpropanoate
  参考文献：
  名称：

  2-烷基-2-苯基-1,3-二氧戊环与一氯化碘的反应：α-苯基链烷酸酯的形成

  摘要：

  用二氯甲烷中的一氯化碘处理后，2-烷基-2-苯基-1,3-二氧戊环经历高产率的转化为2-氯乙基α-苯基链烷酸酯。

  DOI：

  10.1039/c39820001311

文献信息

• Probing the Lewis Acidity and Catalytic Activity of the Metal–Organic Framework [Cu3(btc)2] (BTC=Benzene-1,3,5-tricarboxylate)
  作者：Luc Alaerts、Etienne Séguin、Hilde Poelman、Frédéric Thibault-Starzyk、Pierre A. Jacobs、Dirk E. De Vos

  DOI：10.1002/chem.200600220

  日期：2006.9.25

  diffraction, optical microscopy, SEM, X-ray photoelectron spectroscopy, N2 sorption, thermogravimetry, and IR spectroscopy of adsorbed CO. CO adsorbs on a small number of Cu2O impurities, and particularly on the free CuII coordination sites in the framework. [Cu3(btc)2] is a highly selective Lewis acid catalyst for the isomerization of terpene derivatives, such as the rearrangement of alpha-pinene oxide to

  设计了一种优化程序，用于制备微孔金属有机骨架（MOF）[Cu3（BTC）2]（BTC =苯-1,3,5-三羧酸酯）。通过X射线衍射，光学显微镜，SEM，X射线光电子能谱，N2吸附，热重分析和红外光谱对吸附的CO进行表征。CO吸附在少量Cu2O杂质上，尤其是在游离CuII上框架中的协调站点。[Cu3（BTC）2]是用于萜烯衍生物异构化的高选择性路易斯酸催化剂，例如将α-pine烯氧化物重排为樟脑醛和将香茅醛环化为异胡薄荷醇。通过使用2-溴苯乙酮的乙烯缩酮作为测试底物，证明了[Cu3（BTC）2]中的活性位是硬路易斯酸。催化剂稳定性，
• Enantioselective inhibition: strategy for improving the enantioselectivity of biocatalytic systems
  作者：Zhi Wei Guo、Charles J. Sih

  DOI：10.1021/ja00199a053

  日期：1989.8

  enantiomerically pure (R)-(+)-DCPP and (S)-(-)-DCPP. The observed inhibition pattern was that of partial noncompetitive inhibition for (R)-(+)-DCPP and that of pure noncompetitive inhibition for (S)-(-)-DCPP. Enantioselective biocatalysis in aqueous' and nonaqueousZ media is becoming increasingly important as a possible alternative method for the resolution of enantiomers. In recent years, hydrolytic enzymes such

  发现右美沙芬 (DM) 和左美沙芬 (LM) 是圆柱假丝酵母脂肪酶催化的多种 (*)-芳基丙酸酯和 (&)-(芳氧基)丙酸酯水解的有效对映选择性抑制剂。在 DM 或 LM 存在下，(&)-甲基 2-(2,4-二氯苯氧基)丙酸酯 (DCPP) 的生物催化拆分的对映选择性提高了 20 倍。已经开发了对映选择性抑制的通用模型，并且已经导出了定量表达式以显示控制对映选择性抑制的潜在参数。为了确定 DM 的作用机制，使用对映异构纯的 (R)-(+)-DCPP 和 (S)-(-)-DCPP 进行了一系列动力学抑制实验。观察到的抑制模式是 (R)-(+)-DCPP 的部分非竞争性抑制和 (S)-(-)-DCPP 的纯非竞争性抑制。水介质和非水介质中的对映选择性生物催化作为拆分对映体的一种可能的替代方法变得越来越重要。近年来，水解酶如猪肝酶、猪胰脂肪酶 Ic 和微生物脂肪酶 Ic (EC 3.1.1.3)
• Improving the enantioselectivity of biocatalytic resolution of racemic compounds
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：EP0387068A1

  公开（公告）日：1990-09-12

  A method of improving the enantioselectivity of biocatalytic resolution of racemic compounds by using an inhibitor to selectively block one of the competing enantiomer reactions.

  一种通过使用抑制剂选择性地阻断竞争对映体反应之一来提高外消旋化合物生物催化解析对映体选择性的方法。
• Giusti,G., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 273, p. 257 - 260
  作者：Giusti,G.

  DOI：——

  日期：——
• CC bond formation strategy through ecocatalysis: Insights from structural studies and synthetic potential
  作者：Claire Garel、Brice-Loïc Renard、Vincent Escande、Anouk Galtayries、Peter Hesemann、Claude Grison

  DOI：10.1016/j.apcata.2015.01.021

  日期：2015.9

  We report the elaboration of novel bio-sourced ecocatalysts for Heck and Suzuki cross-coupling reactions. Ecocatalysis is based on the recycling of metals issued from phytoremediation or rehabilitation, and an innovative chemical valorization of the subsequent biomass in the field of catalysis. Here, we describe the efficient palladium accumulation by plants (Brassica juncea, Lolium multiflorum) via rhizofiltration. Taking advantage of the remarkable ability of the selected plants to accumulate Pd(II) species into their roots, these latter can be directly used for the preparation of ecocatalysts, called Eco-Pd (R). The formed Eco-Pd (R) catalysts are thoroughly characterized via ICP-MS, XRD, XPS, TEM, SEM in order to elucidate the chemical composition and morphology of the formed materials. Significant differences to conventional Pd-based catalysts such as palladium(II) chloride can principally be related to a particular Lewis acid behavior of the Eco-Pd (R) catalysts. Finally, the obtained Eco-Pd (R) appear as highly active catalysts in Heck and Suzuki cross-coupling reactions necessitating considerably lower Pd quantity compared to precedently reported bio-sourced palladium containing catalysts. (C) 2015 Elsevier B.V. All rights reserved.