(R)-methyl 2-(allyloxy)-2-phenylacetate | 95237-07-3

• 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: (R)-methyl 2-(allyloxy)-2-phenylacetate
• 英文别名: methyl 2-(allyloxy)-2-phenylacetate；(R)-Methyl 2-allyloxy-2-phenylacetate；methyl (2R)-2-phenyl-2-prop-2-enoxyacetate
• CAS: 95237-07-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: WJURZVWJABCBMX-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-(allyloxy)-2-phenylacetate 在 potassium permanganate 、 lithium aluminium tetrahydride 、 硫酸 、 D(+)-10-樟脑磺酸 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 trans-methyl 5-phenyl-1,4-dioxane-2-carboxylate
  参考文献：
  名称：

  Favourable involvement of α2A-adrenoreceptor antagonism in the I2-imidazoline binding sites-mediated morphine analgesia enhancement

  摘要：

  Aim of the present study was to obtain novel alpha(2)-adrenoreceptor (alpha(2)-AR) antagonists, possibly endowed with subtype-selectivity. Therefore, inspired by the non subtype-selective alpha(2)-AR antagonist idazoxan, we designed 1,4-dioxane derivatives bearing an aromatic area in position 5 or 6 and the imidazoline nucleus in position 2. Among the novel molecules 1-6, compound 2, with a trans stereochemical relationship between 5-phenyl and 2-imidazoline groups, was able to antagonize the sole alpha(2A)-subtype. Moreover, 2 showed an affinity at I-2-imidazoline binding sites (I-2-IBS) comparable to that at alpha(2A)-AR. In in vivo studies 2 strongly increased morphine analgesia. This interesting behaviour appeared to be induced by the favourable involvement of alpha(2A)-AR antagonism in the I-2-IBS-mediated morphine analgesia enhancement. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.016
• 作为产物：
  描述：

  (R)-(-)-扁桃酸甲酯 、 3-溴丙烯 在 silver(l) oxide 作用下， 以 乙醚 为溶剂， 反应 50.0h， 以78%的产率得到(R)-methyl 2-(allyloxy)-2-phenylacetate
  参考文献：
  名称：

  Alternative Sm(II) Species-Mediated Cascade Coupling/Cyclization for the Synthesis of Oxobicyclo[3.1.0]hexane-1-ols

  摘要：

  The allylSmBr/HMPA/MsOH system has been found to be an efficient reagent for the "ester-alkene" coupling/cyclization cascade of readily available a-allyloxy esters. Oxobicyclo[3.1.0]hexane-1-ols were thus prepared in good to excellent yields and diastereoselectivities. Investigation on the mechanism suggested the possible existence of a new Sm(II) species, namely, CH3SO3SmBr, which resulted from the reaction between allylSmBr and MsOH and may be the actual SET reagent.

  DOI：

  10.1021/acs.orglett.7b03613

文献信息

• Enantioselective C−C Bond Formation by Rhodium-Catalyzed Tandem Ylide Formation/[2,3]-Sigmatropic Rearrangement between Donor/Acceptor Carbenoids and Allylic Alcohols
  作者：Zhanjie Li、Huw M. L. Davies

  DOI：10.1021/ja9075293

  日期：2010.1.13

  The rhodium-catalyzed reaction of racemic allyl alcohols with methyl phenyldiazoacetate or methyl styryldiazoacetate results in a two-step process, an initial oxonium ylide formation followed by a [2,3]-sigmatropic rearrangement. This process competes favorably with the more conventional O-H insertion chemistry as long as donor/acceptor carbenoids and highly substituted allyl alcohols are used as substrates

  外消旋烯丙醇与苯基重氮乙酸甲酯或苯乙烯基重氮乙酸甲酯的铑催化反应产生一个两步过程，首先形成氧鎓叶立德，然后进行 [2,3]-σ 重排。只要使用供体/受体类卡宾和高度取代的烯丙醇作为底物，该过程就可以与更传统的 OH 插入化学竞争。当反应由 Rh(2)(S-DOSP)(4) 催化时，会以高对映选择性 (85-98% ee) 产生具有两个相邻季中心的叔 α-羟基羧酸衍生物。
• Enantioselective iron-catalysed O–H bond insertions
  作者：Shou-Fei Zhu、Yan Cai、Hong-Xiang Mao、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1038/nchem.651

  日期：2010.7

  environmentally benign character of iron mean that it is an ideal alternative to precious metals in catalysis. Recent growth in the number of iron-catalysed reactions reported reflects an increasing demand for sustainable chemistry. Only a limited number of chiral iron catalysts have been reported and these have, in general, proven less enantioselective than other transition-metal catalysts, thus limiting their

  铁的易得性、低廉的价格和环境友好的特性意味着它是催化中贵金属的理想替代品。最近报道的铁催化反应数量的增长反映了对可持续化学的需求不断增加。仅报道了有限数量的手性铁催化剂，并且通常证明这些手性铁催化剂的对映选择性低于其他过渡金属催化剂，因此限制了它们的吸引力。在这里，我们报告螺-双恶唑啉配体的铁配合物是不对称 O-H 键插入反应的高效催化剂。这些配合物催化插入各种醇甚至水的 O-H 键，在温和的反应条件下具有出色的对映选择性。选择性超过了用其他过渡金属催化剂获得的选择性。
• Alternative Sm(II) Species-Mediated Cascade Coupling/Cyclization for the Synthesis of Oxobicyclo[3.1.0]hexane-1-ols
  作者：Bingxin You、Mengmeng Shen、Guanqun Xie、Hui Mao、Xin Lv、Xiaoxia Wang

  DOI：10.1021/acs.orglett.7b03613

  日期：2018.2.2

  The allylSmBr/HMPA/MsOH system has been found to be an efficient reagent for the "ester-alkene" coupling/cyclization cascade of readily available a-allyloxy esters. Oxobicyclo[3.1.0]hexane-1-ols were thus prepared in good to excellent yields and diastereoselectivities. Investigation on the mechanism suggested the possible existence of a new Sm(II) species, namely, CH3SO3SmBr, which resulted from the reaction between allylSmBr and MsOH and may be the actual SET reagent.
• Favourable involvement of α2A-adrenoreceptor antagonism in the I2-imidazoline binding sites-mediated morphine analgesia enhancement
  作者：Valerio Mammoli、Alessandro Bonifazi、Fabio Del Bello、Eleonora Diamanti、Mario Giannella、Alan L. Hudson、Laura Mattioli、Marina Perfumi、Alessandro Piergentili、Wilma Quaglia、Federica Titomanlio、Maria Pigini

  DOI：10.1016/j.bmc.2012.02.016

  日期：2012.4

  Aim of the present study was to obtain novel alpha(2)-adrenoreceptor (alpha(2)-AR) antagonists, possibly endowed with subtype-selectivity. Therefore, inspired by the non subtype-selective alpha(2)-AR antagonist idazoxan, we designed 1,4-dioxane derivatives bearing an aromatic area in position 5 or 6 and the imidazoline nucleus in position 2. Among the novel molecules 1-6, compound 2, with a trans stereochemical relationship between 5-phenyl and 2-imidazoline groups, was able to antagonize the sole alpha(2A)-subtype. Moreover, 2 showed an affinity at I-2-imidazoline binding sites (I-2-IBS) comparable to that at alpha(2A)-AR. In in vivo studies 2 strongly increased morphine analgesia. This interesting behaviour appeared to be induced by the favourable involvement of alpha(2A)-AR antagonism in the I-2-IBS-mediated morphine analgesia enhancement. (C) 2012 Elsevier Ltd. All rights reserved.