(+/-)-2-methyl-3-phenyl-1-propyl acetate | 79211-56-6

• 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-methyl-3-phenyl-1-propyl acetate
• 英文别名: (+/-)-3-phenyl-2-methyl-1-propyl acetate；2-methyl-3-phenylpropyl acetate；(±)-2-methyl-3-phenylpropyl acetate；acetic acid-(2-methyl-3-phenyl-propyl ester)；Essigsaeure-(2-methyl-3-phenyl-propylester)；(2-methyl-3-phenylpropyl) acetate
• CAS: 79211-56-6
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: REIIUUVNECGOHA-UHFFFAOYSA-N

物化性质

• 沸点：
  90-92 °C(Press: 0.6 Torr)
• 密度：
  1.000±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：
  0.42
• 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-methyl-3-phenyl-1-propyl acetate 在 甲醇 、 lithium hydroxide 作用下， 生成 2-甲基-3-苯丙醇
  参考文献：
  名称：

  亚磷酸-吡啶/铱配合物库作为高度选择性催化加氢最小功能化烯烃的催化剂。

  摘要：

  易于获得的亚磷酸酯-吡啶配体的模块库已成功地首次用于铱催化的各种最小官能化烯烃的不对称加氢中。已经表明，模块化配体设计对于寻找每种底物的高选择性催化体系至关重要。因此，在各种E-和Z-三取代烯烃（包括要求更高的三芳基取代的烯烃和二氢萘）中都获得了优异的对映选择性（ee高达99％）。良好的性能扩展到极富挑战性的末端二取代烯烃种类，并扩展到包含相邻极性基团的烯烃（ee最高可达99％）。通过简单地改变亚磷酸酯部分旁边的碳的构型，可以以优异的对映选择性获得还原产物的两种对映异构体。还使用碳酸亚丙酯作为溶剂进行氢化，这使得铱催化剂可以重复使用并保持优异的对映选择性。

  DOI：

  10.1002/adsc.201201017
• 作为产物：
  描述：

  2-苄基丙酸 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (+/-)-2-methyl-3-phenyl-1-propyl acetate
  参考文献：
  名称：

  光学活性β-烷基取代的γ-内酯和威士忌内酯类似物的合成和嗅觉评价

  摘要：

  合成了具有光学活性的β-烷基取代的γ-内酯和威士忌内酯类似物，并评估了其气味特性。在手性中间体的制备过程中，我们发现了3-芳基甲基-2-甲基-1-丙醇的高度对映选择性酯化反应的良好反应条件，以动力学方式将它们拆分。合成内酯的嗅觉评价结果表明，γ-内酯环上的烷基对气味分布起重要作用。

  DOI：

  10.1016/j.tet.2020.130984

文献信息

• Iridium Catalysts with Chiral Imidazole-Phosphine Ligands for Asymmetric Hydrogenation of Vinyl Fluorides and other Olefins
  作者：Päivi Kaukoranta、Mattias Engman、Christian Hedberg、Jonas Bergquist、Pher G. Andersson

  DOI：10.1002/adsc.200800062

  日期：2008.5.5

  New chiral bidentate imidazole-phosphine ligands have been prepared and evaluated for the iridium-catalysed asymmetric hydrogenation of olefins. The imidazole-phosphine-ligated iridium catalysts hydrogenated trisubstituted olefins with the same sense of enantiodiscrimination as known iridium catalysts possessing oxazole and thiazole as N-donors. The imidazole-based catalysts were shown to hydrogenate

  制备了新的手性二齿咪唑-膦配体，并进行了铱催化的烯烃不对称氢化的评估。与已知的具有恶唑和噻唑作为N-给体的铱催化剂一样，咪唑-膦连接的铱催化剂以对映异构的相同含义氢化三取代的烯烃。已显示基于咪唑的催化剂可氢化氟乙烯，在某些情况下，迄今公布的ee值最高。
• HYDROXY FORMAMIDE DERIVATIVES AND THEIR USE
  申请人：GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED

  公开号：US20160340328A1

  公开（公告）日：2016-11-24

  Disclosed are compounds having the formula: wherein R1, R2 and R3 are as defined herein, and methods of making and using the same, including use as inhibitors of BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.

  揭示了具有以下公式的化合物：其中R1、R2和R3如本文所定义，并且制备和使用这些化合物的方法，包括用作BMP1、TLL1和/或TLL2的抑制剂以及用于治疗与BMP1、TLL1和/或TLL2活性相关的疾病。
• Highly enantioselective kinetic resolution of primary alcohols of the type Ph-X-CH(CH3)-CH2OH by Pseudomonas cepacia lipase: effect of acyl chain length and solvent
  作者：Alessandra Mezzetti、Curtis Keith、Romas J. Kazlauskas

  DOI：10.1016/j.tetasy.2003.09.049

  日期：2003.12

  Although lipase from Pseudomonas cepacia (PCL) shows high enantioselectivity towards many secondary alcohols, it usually exhibits only low to moderate enantioselectivity towards primary alcohols. To increase this enantioselectivity, we optimised the reaction conditions for the PCL-catalysed hydrolysis of esters of three chiral primary alcohols: 2-methyl-3-phenyl-1-propanol 1, 2-phenoxy-1-propanol 2 and solketal 3. The enantioselectivity towards 1-acetate increased from E=16 to 38 upon changing the solvent from ethyl ether/phosphate buffer to 30% n-propanol in phosphate buffer and increased again to E greater than or equal to 190 upon changing the substrate from 1-acetate to 1-heptanoate. The same changes increased the enantioselectivity towards alcohol 2 from E=17 to 70, but did not significantly increase the enantioselectivity towards alcohol 3. The best solvent was similar to the solvent used to crystallise the open form of PCL and likely stabilises the open form of PCL. This stabilisation may increase the enantioselectivity by removing kinetic contributions from a non-enantioselective lid-opening step. We determined the kinetic contribution of the lid-opening step by measuring the interfacial activation of PCL. The activation energy for the PCL-catalysed hydrolysis of ethyl acetate was at least 2.6 kcal/mol lower in the presence of a water-organic solvent interface. (C) 2003 Elsevier Ltd. All rights reserved.
• A drop of enantioselectivity in the Pseudomonas cepacia lipase-catalyzed ester hydrolysis is influenced by the chain length of the fatty acid
  作者：Andrea Tafi、Fabrizio Manetti、Maurizio Botta、Silvana Casati、Enzo Santaniello

  DOI：10.1016/j.tetasy.2004.06.010

  日期：2004.8

  A two-step molecular mechanics based computational procedure has been applied to explain the enantioselectivity observed in the hydrolysis of esters of primary alcohols, carried out in the presence of a lipase from Pseudomonas cepacia. This approach proved to be very effective in explaining an unpredictable drop in enantioselectivity, experimentally observed when the chain of the fatty acid was lengthened and to predict the chain length in correspondence of which the effect should have revealed itself. (C) 2004 Elsevier Ltd. All rights reserved.
• US4601797A
  申请人：——

  公开号：US4601797A

  公开（公告）日：1986-07-22